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Key West Cottages

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 23
    5 of 5 stars (4) Excellent
    Studio / 1 Bathroom / Sleeps 2
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    1 / 17
    5 of 5 stars (2) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 4
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    5 of 5 stars (7) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    5 of 5 stars (1) Excellent
    Studio / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Grill
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    About this property
    Part of Southernmost Sanctuary Suites The Osprey Suite (Formerly the Osprey Suite) - Located in the Garden at the Southernmost Studios, the Osprey Suite is the perfect island getaway. Located within walking distance to all of the charms in Old Town you'll never want to leave! The Osprey has a... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 29 August 2014
    This was a last minute booking for us.. we had no idea what type of room we would be getting. Boy were we surprised! The gate is a little hard to find at first and you begin to...
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    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights*** MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO EXCEPTIONS Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light and bright... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 18 March 2015
    Stayed here for 2 months while I was having my house remodeled and I was very pleased with the facilities and the unit. The condo has been nicely redone and very well stocked...
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    1 / 23
    4.5 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    Two bedrooms, two and a half baths, Foundry Condo 121 Front Street in the Truman Annex, is located in the heart of Key West's Old Town. Fly in and take a taxi from the Key West airport or the Keys Shuttle from the Miami or Ft. Lauderdale airports. One reserved vehicle parking space. Available for... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 20 May 2014
    My husband & I, along with another couple, rented this condo for a week in May 2014. We found the condo to be larger than expected & quite comfortable for 4 adults. Living area...
    5 of 5 stars Reviewed 21 August 2011
    We had a great time staying at the Foundry Unit 6. The unit is very well decorated and has everything you need, it almost feels like if you are at home. Dave Lewis is wonderful to...
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    1 / 17
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    RENTAL RATES ARE NEGOTIABLE PLEASE SEE 'RATES' FOR SPECIAL OFFERS The City of Key West requires that we rent the house to you for a twenty-eight (28) day rental period, so if you, your family, friends, or guests want to use the house at any time during the twenty-eight (28) day rental... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 5 May 2010
    The best place to have a taste of old Key West. Not at all like anything you would rent anywhere else in the country!It was walking distance to everything in Old Town and the...
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    1 / 30
    5 of 5 stars (10) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    A Key West Gem! Fine dining abounds here with great restaurants such as Square One, Origami Sushi Bar and Panini/Panini, which offers free wi-fi). In the “must have” location of historic, old town Key West, it is a second story home-away-from-home, just steps from the sights, sounds and... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 25 June 2014
    Had a great time staying in this condo with 4 of my besties! We enjoyed having plenty of space...upstairs and downstairs, 2.5 baths...great for 5 women! The location of the...
    5 of 5 stars Reviewed 17 April 2014
    This is a fantastic complex and is managed/owned by Rick who will go out of his way to make you happy. He picked us from the airport, fishing and back in his Escalade at no...
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    1 / 15
    4 of 5 stars (7) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one... View all property information
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    Location Information
    Key West, Florida Keys 33040
    2 of 5 stars Reviewed 2 February 2014
    Although we enjoyed our holiday in Key West, we were disappointed in the quality of this rental, particularly in light of the cost: - The toilet in the master bath was...
    2 of 5 stars Reviewed 8 January 2014
    This could be a lovely house, spacious and in a good location if it was just cleaned and refurbished. The pictures online need updated. They do not reflect the current condition...
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    1 / 27
    4 of 5 stars (23) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
    traveller have booked this property
    Overview Reviews (23) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Southernmost Retreat features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. The perfect place to listen to your favorite music while... View all property information
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    Location Information
    Key West, Florida Keys 33040
    2 of 5 stars Reviewed 22 April 2015
    I stayed at this location in February with my husband and a friend, and we THOUGHT we enjoyed the cleanliness, location, etc. UNTIL 2 days after we checked out, my friend's...
    4 of 5 stars Reviewed 23 January 2015
    We just spent a week at SMR and really enjoyed our stay! Close to duval without the noise! We could hear some live music from la te da one night, but it was nice to sit on the...
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    4.5 of 5 stars (27) Very good
    Studio / 1 Bathroom / Sleeps 2
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    Overview Reviews (27) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    The Truman Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 30 October 2014
    Late reservation so I couldn't be picky. Bed mattress needs to be replaced. Nighttime security light didn't work. Pool nice. Clean full kitchen
    5 of 5 stars Reviewed 7 June 2014
    The home was clean and quiet. It was just perfect for the two of us. We would recommend it to others.
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    1 / 26
    5 of 5 stars (1) Excellent
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Brand New to the Rental Market! Part of Banana's Foster Guest House This cozy 2nd floor studio is perfect for a couple looking to be in the middle of the Duval action! After entering the compound from the shared off street parking into the courtyard with shared plunge pool and BBQ grill, go... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 12 November 2014
    This place was perfect for what we were looking for: Close to Duval, Close to Front Street, Pet Friendly, Shared Space but still alot of privacy. It is a small one bedroom, one...
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    4 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Come down and take part in in Key West's many fishing tournaments this summer! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family... View all property information
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    Location Information
    Key West, Florida Keys 33040
    2 of 5 stars Reviewed 16 April 2014
    We certainly did not get what we thought we were paying for. WiFi was virtually non-existent. The "fully-equipped" kitchen had no serving spoons, only two dish towels, and ants...
    5 of 5 stars Reviewed 11 February 2014
    I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
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    4.5 of 5 stars (17) Very good
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (17) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Part of 4 exclusive units at Abbey Road, renovated January, 2010, this suite is at 918-920 Center Street. Featuring a king pillow-top bed and marble floors, the state-of-the-art kitchen includes granite counter top, a 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 29 January 2015
    The room was very clean with daily housekeeping. The jacuzzi was amazing as was the heated pool next door. Perfect location to get to Duval Street. Can't wait to go back!
    4 of 5 stars Reviewed 3 January 2015
    This was exactly what we were looking for. The location was right in town, but still had a very private feel to it. It was within walking distance to everything, museums, the...
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    $3,170
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    1 / 37
    4 of 5 stars (1) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    A surprise awaits you inside the gates of the Southard Square village. Nestled in the heart of Historic Key West, you will be only 4 blocks from world famous Duval Street and 3 blocks away from the scenic Historic Seaport of Key West. Please see our video!! When you arrive, park your car in your... View all property information
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    Location Information
    Key West, Florida Keys
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    4.5 of 5 stars (24) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Reviews (24) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 15 January 2015
    My husband and I stayed here with another couple and it was great! Great location, lots of room! There is definitely a master suite and a second bedroom but both rooms have...
    5 of 5 stars Reviewed 13 January 2015
    Townhouse was nice,clean,stocked well and as promised .the location was great...walking distance to everything we wanted..quiet..pool was well kept, rental company was accessible...
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    4.5 of 5 stars (15) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 11 December 2014
    Amazing condo ! Great Staff ! Beautiful place with comfy beds and all the comforts of home and then some ! Hot Tub !!! Full kitchen w/washer and dryer. Gated parking and 2 pools...
    5 of 5 stars Reviewed 22 August 2014
    I have stayed in this location once before. They have upgraded the flooring and it looks great. The pool is quiet and relaxing. The unit sits back from Duval Street so there is...
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    5 of 5 stars (1) Excellent
    Studio / 1 Bathroom / Sleeps 2
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Part of Southern Palms ROYAL PALM (formerly Little Palm) - What an idyllic setting! Picture the most perfect romantic getaway cottage with all the must have's for a great Key West vacation - in a setting that nature provided in the late 1800's - the hardwood canopy is stunning! The Tommy Bahama... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 23 December 2014
    This was our second extended stay in this unit and we absolutely love it! You can't beat the location or the privacy of the unit. It's a perfect unit for two! There's a few...
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    5 of 5 stars (25) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 4
    traveller have booked this property
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! The bedroom is decorated in rich tropical colors. A writing desk and chair... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 9 October 2014
    Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
    5 of 5 stars Reviewed 19 August 2014
    My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Sauna
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach ,... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    1 / 10
    4 of 5 stars (55) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (55) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. 7 night minimum rental.Paradise is definitely found in this Non-Smoking,... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 28 April 2014
    Our rental was clean, with plenty of supplies and towels. It was in a gated area and we always felt very safe. I loved sitting on the patio outside, enclosed by foliage so it...
    5 of 5 stars Reviewed 3 September 2013
    It was close to walk to Duval Street and short drive or walk if you like to Fort Zachary Taylor state park for swimming at the beach.
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    4 of 5 stars (9) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This comfortable 2 bedroom unit features a huge oceanfront balcony... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 6 December 2012
    112 Beach Club is a large 2b/2b condo right on the atlantic! The complex is a secure property with very nice amenities. This condo itself is a bit dated, but was very clean and...
    2 of 5 stars Reviewed 3 February 2012
    It was a nice condo, accommodating my wife and I and another couple vacationing with us, but it was dirty. The refrig and appliances were not cleaned, the home was pretty much...
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    4.5 of 5 stars (29) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (29) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Part of the Nightly Group PALM GARDENS Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 18 February 2015
    My wife and I recently rented this unit for the first week of February. Overall, I’d call it a solid good! We liked the location, with a grocery store and an excellent selection...
    5 of 5 stars Reviewed 3 September 2014
    I stayed here this past Labor Day weekend for a friend's bachelorette party. There were 10 of us, and the Heron Hideaway as well as the three other one-bedroom condos in the area...
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    4.5 of 5 stars (8) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 10 February 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 stars Reviewed 30 December 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
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    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Pets allowed
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    • Suitable for children
    • ?
    • x
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    • ?
    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 19 March 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
    5 of 5 stars Reviewed 3 March 2015
    My wife and I stayed in Shelley's Rooftop Hideaway for the entire month of February. It was fantastic, and we had a great time in Key West, due in no small part to the location...
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    5 of 5 stars (40) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
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    • Grill
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • ?
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. It is an upstairs unit with 2 bedrooms and 1 Bathroom with 1 queen, 2... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 25 June 2013
    Stayed at the Shipyard 253 and had a wonderful time. Very nicely decorated, comfortable and a great location - just 2 blocks from Duval St. I would stay there again!
    5 of 5 stars Reviewed 31 May 2013
    Great central location. Walking distance to most things of interest. Liked the fact it's a Gated community with assigned parking place. Not beach front, but that wasn't important...
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    4.5 of 5 stars (15) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
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    • Gym
    • Hot Tub
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • ?
    • ?
    About this property
    Part of ALMOST SOUTHERNMOST RETREAT This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St. The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 2 July 2014
    Our first visit to the Keys celebrating our 28th anniversary with our adult children, (3 couples) this historic cottage slept all 6 of us very comfortably; in fact, the most...
    5 of 5 stars Reviewed 5 February 2014
    We have stayed at this property on previous visits to Key West- it is a great location- close to everything and has plenty of space. Easy to cook at home if you don't want to go...
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    4.5 of 5 stars (21) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Water Views
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly landscaped garden of native Key West plants and trees.... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 26 September 2012
    Our recent stay at Vista Fresco was great. Everything we needed from the blender to extra bath towels was provided. The only issue was something that management could do nothing...
    2 of 5 stars Reviewed 5 July 2012
    We stayed at Vista Fresco in March, 2012 with our 9 & 11 year-old children for Spring Break. I feel like we were mislead about the property in some respects, and we didn't feel...
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    4 of 5 stars (18) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Private Outdoor...
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    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • ?
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    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This spacious 2 bedroom unit features a large oceanfront balcony accessed... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 17 January 2013
    The apartment was great overall. Very spacious and clean and there was a lot provided that I did not expect (ie batteries, beach towels, beach bags, fishing pole, coolers etc...
    4 of 5 stars Reviewed 11 May 2012
    We rented this on recommendation from trip advisor...it was a lovely as it was described. The beds were fantastic!!! The furniture comfortable for a vacation house. Linens...
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    4.5 of 5 stars (8) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • x
    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 26 March 2015
    The people who work on property were very friendly. The main areas in the condo were very clean. The guest bath could have been cleaner. The kitchen had everything you would need...
    5 of 5 stars Reviewed 6 March 2015
    Located in a private condo complex, the unit we stayed in featured excellent amenities while also clean and well maintained. Location to old town and Duval will require...
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    4.5 of 5 stars (27) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 26 January 2015
    We were pleased with the spacious accommodations at the Harbor Island Retreat. The rooms were clean and they (and view) were as depicted on the TA web site. The unit was...
    4 of 5 stars Reviewed 28 November 2014
    Not close to Duvall Street where everything is happening bit we enjoyed it and the unit was nicely decorated and had everything we needed. Huge balcony overlooking pool with a...
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    4.5 of 5 stars (23) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Grill
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    • ?
    About this property
    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (the entrance to Nancy's Secret Garden and 1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 6 April 2015
    The location was perfect and the accommodations good for the price. We had more room than we really needed. The service was good and the shuttle available to assist with to and...
    2 of 5 stars Reviewed 22 January 2015
    We booked with Key West Vacational Rentals and from the start it was a mess. They reserved the wrong dates and when i contacted them about this mix up my cottage had been...
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    4 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Air Conditioning
    • Wi-Fi
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    • Pets allowed
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    • Suitable for children
    • x
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    • ?
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    About this property
    Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they'll say hi to one another even if they've never met. This is your neighborhood during... View all property information
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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 16 February 2015
    comfortable front porch was nice for street watching. think this is over priced 1 1/2 bath but best deal I could find 4-5 months prior. the parking in front of the cottage is...
    5 of 5 stars Reviewed 2 December 2013
    We just stayed here Thanksgiving week and had a great time. It is right off Duval Street and you can walk any where easily. The hot tub is the back yard is very private. The...
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    4.5 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • x
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    About this property
    The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch Cottage. It is a perfect example of turn-of-the-century island architecture. This adorable two bedroom cottage, each with queen bed and TV (the master has a large flat screen), two full baths and queen sleeper-sofa is... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 14 October 2014
    The Bahama House looked just like the pictures and the location was just as advertised-convenient!! The staff at Key West Rentals were quick to respond to issues with pool and...
    5 of 5 stars Reviewed 26 July 2014
    I can say this very simply, this is exactly what you picture in your mind when you think of a quaint bungalow in Key West, except more luxurious. Top notch value.
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    3 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Dishwasher
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    This nightly group rental consists of 3 separate units. 1) Porchside Paradise 2) Orange Blossom Suite 3) Deckside Suite . Three separate bedrooms with queen sized beds. Two sleeper sofas and two private hot tubs! Located at 510 Petronia St, literally steps from Duval St! Take advantage of the... View all property information
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    Key West, Florida Keys 33040
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    4 of 5 stars (25) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Grill
    • Gym
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    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (the entrance to Nancy's Secret Garden and 1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top... View all property information
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    Key West, Florida Keys 33040
    2 of 5 stars Reviewed 3 May 2015
    Key West Vacation Rentals was a great company. The staff was friendly and amenable. Whenever we come down to Key West, we would rent from them again...just not this particular...
    5 of 5 stars Reviewed 25 December 2014
    We only stayed 3 nights and it was the perfect location. The room was clean with all necessities needed. We didn't go to the pool but enjoyed being in walking distance to the...
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    5 of 5 stars (14) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 16
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    • Air Conditioning
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    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
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    About this property
    Almost Southernmost Retreat is made up of Part of ALMOST SOUTHERNMOST and Part of ALMOST SOUTHERNMOST TOOon the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets. This style is common throughout the islands. Located in a row of identical cigar-maker... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 2 January 2015
    Three generations, nine people, stayed here over Christmas. We each had space to be by ourselves, and we all had space to get together. Nine of us sat around the table in the...
    5 of 5 stars Reviewed 4 September 2014
    I came to the Almost Southernmost Retreat for my friends bachelorette party for Labor Day weekend 2014. We had 12 girls and there was more than enough room for everyone. This...
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    4.5 of 5 stars (23) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Gym
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • ?
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    About this property
    Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit with Mexican Tile downstairs... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 8 April 2015
    Very well decorated an equipped with everything needed. Nice open area, the pictures do not do it justice. Larger living area and dining than the photos show. Two nice balconies...
    2 of 5 stars Reviewed 12 August 2014
    Overall the unit was nice. A few rips in the living room chair; could use recovering. The kitchen had all the amenities and we lacked for nothing. The master bedroom was very...
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    4.5 of 5 stars (20) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    • Suitable for children
    • x
    • x
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    • x
    About this property
    CALL AND ASK ABOUT OUR WEEKLY SPECIAL WITH 1 NIGHT FREE! You will love staying in this great Key West historic old town location where 90% of the residents are local. They each have an interesting Key West tale to tell and are a very warm,friendly and diverse group. Here you will absorb the... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 8 April 2015
    The cutest little condo! Only blocks from Duval street, bike rental on the end of the street, tons of little restaurants, centrally located to EVERYTHING!!!! I would recommend it...
    3 of 5 stars Reviewed 5 March 2015
    We will go to a hotel in the future. The apartment was cute but when we arrived one of the a/c units didn't work, the porch light didn't work, the light on the ceiling fan in the...
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    Studio / 1 Bathroom / Sleeps 4
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    Part of Southernmost Suites The Pelican Suite is located in The Southernmost Suites on historic Simonton Street. Tucked back within the garden the Spoonbill Suite offers a serene escape from the hustle and bustle. The Pelican Suite has 2 Queen Beds and a kitchenette for you to enjoy meals in... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 stars (6) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
    • x
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    • Elder access
    • ?
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    About this property
    Part of ALMOST SOUTHERNMOST RETREAT Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 26 July 2014
    This is our second time staying in this property. We stayed here again because the property manager & his team were fantastic, the property was very clean and it was a great...
    5 of 5 stars Reviewed 6 June 2014
    Very clean, looks recently redone. Great set up, plenty of room for the six of us. Most comfortable bed ever. Literally steps from Duval St. I would definitely stay here again.
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    4.5 of 5 stars (8) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The superb location at the top of Solares Hill, three blocks to the Historic Seaport and Duval Street, one block to the Public Library; Casa 625 will amaze you with the detailing, decorating and attention to... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 24 December 2013
    The house is my perfect idea of what a Key West Conce Cottage should be. With Dade County pine walls, heated pool, all modern conveniences and perfect location for quite and easy...
    5 of 5 stars Reviewed 2 November 2013
    Really enjoyed the comfort of the unit. Close to everything but no need to leave!
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    4.5 of 5 stars (2) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Gym
    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 4 February 2011
    We spent the month of March at Villa azul in 2008. It was amazing. We discovered Key West in a way I never thought possible...some of our best moments were spent in the oasis...
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    4.5 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Dishwasher
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    • Internet Access
    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • ?
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    About this property
    30 DAY MINIMUM RENTAL This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central location to get to the Historic seaport or new town. The light & airy combined living/dining area with its soft color toned furnishings, hardwood floors & many windows... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 7 February 2013
    We really loved the cottage and did appreciate all the little extras our host had provided. The location couldn't have been more convenient. We rented bicycles but could have...
    5 of 5 stars Reviewed 27 June 2009
    I have rented the Angla Cottage for the past three seasons. The house is very comfortable with space for guests in a separate portion of thje house. Swimming pool is great, and...
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    4.5 of 5 stars (16) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    This weekly (minimum) condo is in a perfect location for enjoying all the sights of Old Town Key West - a car is not even necessary as you can walk to everything! Fly in to Key West or take the Keys Shuttle from the Miami or Ft. Lauderdale airports. This rare condominium with a second full bath... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 20 August 2014
    Upon arrival we found condo clean and prepared for us. Location is excellent: 2 min to Duval Street, 15 min to Mallory square, 3 min ride or 10 min walk to Fort Zachary State Park...
    5 of 5 stars Reviewed 29 October 2013
    Drove from Co.,parked our car in assigned parking and rented bikes(The Bike Shop) for the whole week! Biking the side streets was so easy and we were very close , walking...
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    4.5 of 5 stars (8) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Gym
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The Shipyard’s Perch is a great place to stay and play near the water and Old Town Key West! Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 19 September 2014
    Highly recommend this facility to anyone who is looking for a conveniently located, quiet, easily acessable 2 bedroom / 2 bath condo. Our week stay was everything we could...
    5 of 5 stars Reviewed 13 May 2014
    Three friends that I have known since first grade and I traveled to Key West for a week to celebrate the year we all turn 60. Stayed at Shipyard Perch. it was perfect. The 2...
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    $3,170
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    4 of 5 stars (2) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    RENTAL RATES ARE NEGOTIABLE PLEASE SEE 'RATES' FOR SPECIAL OFFERS The City of Key West requires that we rent the house to you for a twenty-eight (28) day rental period, so if you, your family, friends, or guests want to use the house at any time during the twenty-eight (28) day rental... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 11 July 2014
    This property is lovely. With the large main house and several small cottages,it would be great for family reunions. The pool, jacuzzis and landscaping are all beautifully...
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    $4,438
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    5 of 5 stars (3) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 7
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 11 February 2015
    Absolutely loved our stay. Owners were great to work with. Furnishings were warm and inviting. Would definitely stay again!
    5 of 5 stars Reviewed 1 November 2014
    First of all, this hotel is awesome! We went as a group of 8 women and I was thrilled that we only needed two rooms and they were side by side! Had a balcony, and plenty of room...
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    $1,376
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    5 of 5 stars (4) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The Shipyard is a great place to stay and play near the water and Old Town Key West! Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and... View all property information
    Make Enquiry
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 8 January 2015
    We have been going to Key West for the past 15 years and we always stay at Truman Annex. We have been many times throughout the year but in the past six years we have been going...
    5 of 5 stars Reviewed 25 October 2014
    I visit Key West often (twice a year if I can). Over the past couple years, I've been booking exclusively with Key West Vacation Rentals. They have wonderful properties available...
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    From
    $1,014
    / Night
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    1 / 20
    3.5 of 5 stars (9) Average
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    'In-the-know' travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval,... View all property information
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    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 4 March 2015
    The property could use some updating. A little paint and some updated furniture would do wonders. Towels without rust and bleach stains should be considered. But we are used to...
    3 of 5 stars Reviewed 15 December 2014
    My family (a group of 9) stayed here for a week while in Key West for a wedding. Amelia's Hideaway was...ok. The rooftop deck and poolside patio were perfect for sitting outside...
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