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Pet Friendly Holiday Rentals in Key West

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    $4,906
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    1 / 15
    4.5 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    5 of 5 stars (10) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    1 / 30
    4 of 5 stars (1) Very good
    Studio / 1 Bathroom / Sleeps 4
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    1 / 19
    4.5 of 5 stars (37) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (37) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
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    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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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. Our beautiful waterfront... View all property information
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    4 of 5 stars Reviewed 8 July 2014
    1960s property but well maintained with a good pool, new gas grills (all the better for cooking your catch) and located right on the marina. Our unit (1040) was on the first floor...
    4 of 5 stars Reviewed 10 September 2013
    had a great time, I'll be back.
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    1 / 23
    5 of 5 stars (4) Excellent
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    • Air Conditioning
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    The kitchen offers an under-counter fridge, microwave, coffee maker, toaster, blender and everything to cook, prepare and enjoy a light meal…and don’t forget the BBQ grill and Ice-maker by the pool! This very comfortable unit also has a very sexy two-person custom shower with glass door,... View all property information
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    5 of 5 stars Reviewed 1 July 2014
    The unit was clean and in a great location. Maintenance was attentive and cleaning staff also. The only trouble we had was virtually ever night some giant vehicle was running...
    5 of 5 stars Reviewed 4 April 2014
    The place we stayed at was small inside, but big on the outside space. The courtyard was beautiful and added another dimension to the space. Like a living room in the tropics!
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    1 / 27
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
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    About this property
    Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home in the 500 block of Olivia Street. The updated kitchen features granite counter tops and beautiful wooden floors. Your bathroom offers a large walk-in tiled shower. A semi-private pool with... View all property information
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    1 / 24
    5 of 5 stars (1) Excellent
    Studio / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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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    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
    4.5 of 5 stars (37) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (37) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Formerly Amelia St Hideaway With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-styled complex, this 1 bedroom/1 bathroom condominium features a full... View all property information
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    5 of 5 stars Reviewed 4 February 2015
    When I say the bathroom is teeny, I mean it makes a cruise ship bathroom look humungous. If you can get past that, the condo is super cute and comfortable and the location can't...
    4 of 5 stars Reviewed 2 December 2014
    All reviews have mentioned the veranda and the view but their were no chairs next to this unit. Also there was no WiFi. Very comfortable with a really nice kitchen.Quiet building...
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    1 / 34
    4 of 5 stars (23) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (23) Make Enquiry
    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
    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 opens to the living room,... View all property information
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    3 of 5 stars Reviewed 14 March 2015
    We have stayed in quite a few places in Key West, and the location was good, but there are things to be aware of. One thing to know is that it is a vacation rental unit in a...
    1 of 5 stars Reviewed 11 March 2015
    This condo was perfectly situated just off Duval, the management company was professional, and the place was clean and comfortable. However, I will never stay here again. At 3 am...
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    1 / 25
    4.5 of 5 stars (2) Very good
    Studio / 1 Bathroom / Sleeps 4
    traveller have booked this property
    Overview Reviews (2) Make Enquiry
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    • Air Conditioning
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
    • ?
    About this property
    Part of Southernmost Sanctuary Suites Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An adorable front porch to watch the people biking, walking or scooting along. Start your mornings on the porch with your Cuban coffee and a good book... View all property information
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    5 of 5 stars Reviewed 6 August 2014
    The room was a nice size for two friends. It was not fancy, but clean and well equipped. Another plus was the front porch where we sat and people watched while having coffee or a...
    4 of 5 stars Reviewed 26 July 2014
    The Egret Studio is very close to the Southernmost Point and next door to a Cuban cafe, so I had coffee there every morning. The studio is very clean, well appointed and we were...
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    1 / 33
    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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    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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    1 / 26
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • 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
    Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many... View all property information
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    5 of 5 stars Reviewed 6 January 2015
    You can book this place if you do not mind occassional airplanes landing and taking off. This is a great place with very friendly staff. The main center of the Island is 5-10...
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    1 / 35
    4.5 of 5 stars (3) Very good
    Studio / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Part of Southernmost Sanctuary Suites People looking for a vacation getaway in Key West are thrilled when they find a hidden gem like The Seagull Suite - located in the gardens of a private compound called The Sanctuary. Location, charm, and island appeal - the Seagull Suite is located in the... View all property information
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    5 of 5 stars Reviewed 17 October 2014
    We had an excellent experience staying in this studio for our honeymoon. Only drawback was the lack of kitchen equipment which made it difficult to cook a full meal for...
    4 of 5 stars Reviewed 25 September 2014
    It was a great location out of the way but by everything. Also the room was very secluded to the back of the property for a nice romantic time.
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    1 / 25
    4.5 of 5 stars (15) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (15) Make Enquiry
    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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    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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    1 / 18
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Housekeeping...
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Eyebrow House is a very spacious one-bedroom suite with a large front porch and palm tree-filled private fenced-in yard overlooking a quiet side street. Our guests enjoy the best of both worlds as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a half block away.... View all property information
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    1 / 27
    5 of 5 stars (1) Excellent
    Studio / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Part of Southernmost Sanctuary Suites The Ibis Suite is located at The Sanctuary in Old Town key West, Only steps to the action, this studio suite has all the comforts of home but surrounds you in island style! Lush gardens surround the Jacuzzi and the calm atmosphere is exactly what you'll need... View all property information
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    5 of 5 stars Reviewed 30 October 2014
    We have stayed in this lodging five times. It is very clean and service is excellent and friendly. The location is secluded and especially quiet.
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    1 / 28
    4.5 of 5 stars (24) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (24) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Sea Breeze features all the amenities of then some! A full kitchen with glass top stove, dishwasher, icemaker, blender, toaster, coffee maker and radio/CD player to play your favorite Jimmy Buffet CD while enjoying a fresh cup of isn't a better way to start your day in paradise! A covered... View all property information
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    5 of 5 stars Reviewed 18 February 2015
    SEA BREEZE was great we were a block away from the 90miles to Cuba attraction. it was really close to little beach "south beach" it was very clean and had 1 parking spot just...
    4 of 5 stars Reviewed 8 February 2015
    For $1700 for 5 nights, I expected a little more. First, I considered doing laundry on the last day, but the dryer door doesn't close (as evidenced by the tape marks all over it...
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    4.5 of 5 stars (30) Very good
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (30) 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 Mallory 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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    5 of 5 stars Reviewed 24 June 2014
    Wonderful. And 'Ive stayed here several times. We also bring our 2 yorkies I love the Mallory, the Truman. So close to everything. Room is beautiful too. And very reasonable in...
    5 of 5 stars Reviewed 19 June 2014
    Very clean, great location, kitchen well equipped, dog friendly, bed was comfortable, quiet location, shower a little small
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    1 / 31
    4.5 of 5 stars (34) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (34) 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 and Origami Sushi Bar), Casa Caribe is a second story paradise just steps from the sights, sounds and excitement of world-famous Duval Street. Lush and tropical gardens surround this... View all property information
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    4 of 5 stars Reviewed 20 January 2015
    We've been to Key West a number of times, but never in January. We're not party animals or lovers of noise, so I knew to avoid the Mallory Square end of things. This condo was...
    4 of 5 stars Reviewed 12 November 2014
    Casa Caribe was a wonderful place for us to stay while in KW. It's on the quiet end of Duval so don't be deterred by the address, only a few blocks from the Southernmost point...
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    1 / 26
    3 of 5 stars (1) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many... View all property information
    Make Enquiry
    3 of 5 stars Reviewed 24 November 2014
    When we arrived they did not have our reservation in their system eve though I had prepaid. I booked through a third party. I showed them my receipts and they put us in a room...
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    1 / 29
    5 of 5 stars (13) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (13) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This house is in a quiet residential neighborhood where loud boisterous parties are not appropriate. This 2 bedroom, 2 bath, 2 story house has an open floor plan featuring lots of pine walls and floors throughout. Upstairs is the king bedroom and a full bath and downstairs is the second bedroom... View all property information
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    5 of 5 stars Reviewed 10 November 2014
    We were very happy with this house rental. The pictures only hold a small window into this gem. Walking distance to Duval (although a cab was only $6 if needed). Great living...
    3 of 5 stars Reviewed 13 August 2014
    Pros - charming cottage, two bathrooms, private pool, dish washer, washer and dryer, nice bed and linens, just a few blocks from Duval, plenty of street parking. Cons - across...
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    1 / 25
    4.5 of 5 stars (31) Very good
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (31) 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 Monroe 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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    4 of 5 stars Reviewed 17 January 2015
    This rental company is one of the best - I've had numerous occasion to use their services. We arrived very early, but were allowed to park our car at the rental location and walk...
    5 of 5 stars Reviewed 18 November 2014
    We had a great stay and will for sure be staying in one of these cottages again. Great location close to nice restaurants approx midway Duval and North 2 blocks. Stayed for a long...
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    1 / 26
    4.5 of 5 stars (11) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    The kitchen is fully equipped with a glass top stove, refrigerator with ice-maker, microwave and everything needed for cooking a gourmet meal or just heating leftovers! French doors open from the kitchen and breakfast bar onto a private deck with a large 4 person private hot tub, table and chairs,... View all property information
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    5 of 5 stars Reviewed 6 June 2014
    Superb location, ideal for a few days in Key West. Only small but great outside space. Loads of character, only slight negative is the bathroom could do with a little tlc. But...
    4 of 5 stars Reviewed 17 April 2014
    The location was good. Not far from Duval. It was very clean. I really enjoyed the hot tub on the patio. The beds were so comfortable :)) Unfortunately a car was parked in front...
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    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 28 January 2015
    We stayed here once back in 2001. The place hasn't changed. That's good and not so good. Good because the facility met our needs for a short stay to participate in the Key West...
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    $1,014
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    1 / 54
    5 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa... View all property information
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    4.5 of 5 stars (29) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
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    • Shared Outdoor Pool...
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    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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    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 (47) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Inside, you will find all of the comforts of home and This two-story 1880's Cigar Maker's Cottage has been completely renovated and has a living room with 42' flat screen TV/DVD, Queen sleeper sofa, kitchen with dishwasher, dining room and bath (with outdoor shower) on the ground floor.... View all property information
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    4 of 5 stars Reviewed 13 February 2015
    Family House is in a great location -we could walk everywhere we wanted to go in Key West. We were on vacation with 6 adults. The major downside to this house is that the sofa bed...
    5 of 5 stars Reviewed 28 January 2015
    The best. The family members stated it was the best ever. Duval offered the best food and drink. Historical amenities offered an educational amenity to offset the drinking...
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    4.5 of 5 stars (36) Very good
    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
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    • Gym
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    • Pets allowed
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    About this property
    Romantic Retreat features a king pillow-top bed, Tommy Bahama furniture, flat screen TV and tropically inspired original fine art. The recently renovated kitchen includes granite counter tops, under counter refrigerator, microwave, toaster/oven, coffee maker, blender and soft mood lighting under... View all property information
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    5 of 5 stars Reviewed 24 January 2015
    Cozy and comfortable cottage - great location...walking distance to most attractions. Pool and hot tub were welcome amenities. We had a nice vacation.
    5 of 5 stars Reviewed 17 May 2014
    Heaven in the middle of Key West. Beautifully decorated, clean, perfect pool & hot tub, Amazing! Staff is very attentive and replenishes towels, changes garbage, maintains the...
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    4.5 of 5 stars (35) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    One half of the group unit Tradewinds Opposite Windward Isle , the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and... View all property information
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    5 of 5 stars Reviewed 12 February 2015
    Wonderful 2 bedroom one bath home! Private just off Duval but very quiet! private courtyard, hot tub and parking. Comfortable bed, kitchen area well equipped but we never used...
    4 of 5 stars Reviewed 6 June 2014
    This house is the perfect little hideaway. Close enough to Duval and all the action but far enough away that you can shut out the world and just relax. The hot tub is very...
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Dishwasher
    • Dryer
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    • Safe
    • Satellite TV
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    • Pets allowed
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    About this property
    This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! The property is completely private and safe, surrounded by a 6 foot gated fence and tropical landscaping. Due to local zoning laws we... View all property information
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    4.5 of 5 stars (10) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
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    • Private Outdoor...
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    • Pets allowed
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    About this property
    Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom... View all property information
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    5 of 5 stars Reviewed 11 March 2015
    Excellent location, between Duvall and Simonton. Home is decorated nice. Very clean. We had two couples and had plenty of privacy. The pool is so nice and it was heated! Daily...
    5 of 5 stars Reviewed 25 February 2015
    We could not have found a more perfect place to rent for our Girls Weekend- My girlfriends and I enjoyed this house so much! The rooms were big and spacious, the balconies...
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    4.5 of 5 stars (12) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
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    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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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
    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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    5 of 5 stars Reviewed 14 April 2013
    Everything was as promised , great location , very nice and helpful staff .
    5 of 5 stars Reviewed 6 January 2013
    Very spacious with great balcony with dock/pool access. Would definitely stay again
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    4.5 of 5 stars (34) Very good
    3 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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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
    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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    4 of 5 stars Reviewed 9 July 2014
    We had a large group visiting Key West for the Swim Around Key West annual event. We had plenty of space for all 10 of us to sleep comfortably. The washer and dryer were very...
    4 of 5 stars Reviewed 20 June 2013
    Had 7 friends stay in the St. Kitts for a long weekend. Rooms were great - there was a lot of space for all of us, with plenty of bathrooms (4), balconies, kitchen, etc. Never...
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    4.5 of 5 stars (22) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
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    • Pets allowed
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    • x
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    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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    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...
    4 of 5 stars Reviewed 24 November 2014
    Location right on Duval was awesome! We were close to everything! The condo has a great layout. Fully functional kitchen. 2 bedrooms with TVs. Outdoor space with hot tub which...
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    4 of 5 stars (25) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • 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. Our beautiful waterfront... View all property information
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    4 of 5 stars Reviewed 10 March 2014
    Traveled with wife and brother and his wife. Very clean, nice size 1200 sf, convenient layout, Pool was nicely heated, adequate parking. about 3/4 of a mile from Malory Square...
    4 of 5 stars Reviewed 12 July 2013
    The condo was nice, a few updates are in order. More cooking untesils and cookware would be nice. Overall, clean, nice location, friendly neighbors and friendly and helpful...
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    4.5 of 5 stars (27) Very good
    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
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    • Satellite TV
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    • Pets allowed
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    • Suitable for children
    • x
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    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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    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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    4.5 of 5 stars (28) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Air Conditioning
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    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • 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. Our beautiful waterfront... View all property information
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    5 of 5 stars Reviewed 22 August 2013
    This was an excellent location, rooom and staff for a week or more stay. We enjoyed it.
    4 of 5 stars Reviewed 13 July 2013
    Docking & unit satisfactory.
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    4.5 of 5 stars (9) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
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    • Pets allowed
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    • x
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    About this property
    Located in Duval Square (between Duval St and Simonton St) where fine and varied dining abounds (Square One, Origami Sushi Restaurant and New York Garden Cafe), This development extends from Duval Street to Simonton Street and is in the heart of historic Old Town. It is comprised of residential... View all property information
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    4 of 5 stars Reviewed 15 March 2015
    The apartment was very comfortable and spacious. It is centrally located and although it's a little noisy at meal times, it is not a problem at night. It does need some minor...
    4 of 5 stars Reviewed 13 January 2015
    We spent 5 nights at Casa Key West and enjoyed our stay . Great location for us . Planning on returning soon.
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    4.5 of 5 stars (17) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 7
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    • Air Conditioning
    • Balcony
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    • Shared Outdoor Pool...
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Short walk to Fort Zachary State Park and South Beach! 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.... View all property information
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    5 of 5 stars Reviewed 28 September 2014
    Very, very nice! Comfortable and clean too. Only complaint is the roosters next door crowing early in the morning. Very audible on the master bedroom side of the unit.
    5 of 5 stars Reviewed 20 August 2014
    Traveling with a group of six people, we found Casa Bonita to be the perfect location for our stay in Key West. The property is gorgeous and incredibly well taken care of; and...
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
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    • Internet Access
    • Private Outdoor...
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    • Pets allowed
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    • x
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    About this property
    2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered... View all property information
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    5 of 5 stars (1) Excellent
    Studio / 1 Bathroom / Sleeps 2
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    • Pets allowed
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    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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    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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    4.5 of 5 stars (31) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Grill
    • Gym
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    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Located on one of old town's prettiest historic streets, Frances Street. Casa Serendipity is one of the finest examples of the 'conch cottage' style architecture that Key West is famous for. Designed to accommodate a family, this three-bedroom home has two full baths, one full bath upstairs and... View all property information
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    4 of 5 stars Reviewed 12 November 2014
    The house was great. Roofs are a little low upstairs but still good enough. Nice patio area and a pool in the backyard. Only a few minutes walking distance from Duval St.
    2 of 5 stars Reviewed 28 October 2014
    My friends and myself stayed at this house during the week of Fantasy Fest in October of 2014. The house was nice, but was too far from town to walk everyday. Next time we will...
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    4 of 5 stars (37) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Gym
    • Hot Tub
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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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    About this property
    Overlooking the gardens and lily pond, the entrance to this spacious unit is through a totally enclosed private decked courtyard with a 4-person spa, table and chairs. Inside this spacious unit you will find a living room with cathedral ceilings, 56” TV, A/C, stereo, queen sleeper sofa and fabulous... View all property information
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    5 of 5 stars Reviewed 27 January 2015
    Wonderful property, great location for walking around Key West. Rooftop deck for morning coffee and enclosed patio. Parking is at a premium, especially around the property, so...
    5 of 5 stars Reviewed 5 November 2014
    My wife and I stayed at the Sunset Suite - Nightly which is managed by Key West Vacation Rentals. This was our first trip to Key West as we went for the Meeting of the Minds. We...
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    5 of 5 stars (25) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
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    • Suitable for children
    • x
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    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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    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
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    • Air Conditioning
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    • Sauna
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
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    • Pets allowed
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    • Suitable for children
    • x
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    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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    4.5 of 5 stars (30) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Gym
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    • Satellite TV
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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
    This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of the line flat screen TV and stereo. The living room has tropical furniture and a w/ Queen Sleeper Sofa. Efficiency kitchen is fully equipped for cooking w/... View all property information
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    3 of 5 stars Reviewed 2 December 2014
    Wonderful location, quiet. In desperate need of upgrades, 2 burner stovetop not fixed but portable one available, ac in bedroom starts and stops every 5 minutes...several cracked...
    4 of 5 stars Reviewed 18 November 2014
    Nice,good location but no parking onsite 95% of time. Had to park 2 blocks away. Cooktop did not work so had to use portable 110 volt spare.
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    4.5 of 5 stars (32) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • 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. Our beautiful waterfront... View all property information
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    4 of 5 stars Reviewed 19 September 2013
    Relaxing fun time with friends. Rented beach cruisers and saw the island.
    5 of 5 stars Reviewed 19 July 2013
    Excellent friendly,clean, lots of linen and supplies. Rooms large and very cozy. loved the balconies and outside furniture. Everyone had smiles on their faces,it made you feel...
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    5 of 5 stars (21) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Grill
    • Hot Tub
    • Internet Access
    • 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
    Part of 4 exclusive units at Abbey Road, The original Cuban tile has been preserved throughout the house, wherever possible. Upon entering the spacious living room, a large tropical sectional queen sleeper sofa allows you to comfortably watch the 46” flat screen TV/DVD. Also available is an I-Pod... View all property information
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    5 of 5 stars Reviewed 8 December 2014
    My spouse brought me to KW to celebrate my birthday, what a truly wonderful time we experienced on our entire trip. Lennon Lodge was absolutely cozy, comfortable, and private...
    5 of 5 stars Reviewed 31 October 2014
    We stayed in Lennon's Lodge for 7 days, and wish we could have stayed forever. The property itself is clean, quiet and private and the Lodge itself is beautiful, well-kept and...
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    4.5 of 5 stars (9) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Amelia House is surrounded by fine restaurants, art galleries, and fine shopping. The living room incorporates a sofa and chairs, in a colorful Caribbean print, which compliments the soft peach wall color. Included are rattan tables to complete the comfortable ambiance of the great room which... View all property information
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    4 of 5 stars Reviewed 14 January 2015
    Great location! 1/2 a block off the main street (Duval) and convenient to everything, but in a quiet dead end street. Private parking! (Hard to park anywhere in the Keys...
    5 of 5 stars Reviewed 13 January 2015
    Its just a few steps away from where all the actions is. Considering the location, it is actually quiet at night. We got ourselves lock out while drinking and partying at the...
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    $236
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Located on a quiet residential street in the beautiful Key West neighborhood of Casa Marina, A Low Key Paradise has a beautiful open layout, with views of the large private patio and pool visible as soon as you enter. Guests can walk to nearby Higgs beach, and Higgs beach dog park— perfect for your... View all property information
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