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Key West Apartments, FL

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$174
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1 / 28
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Studio, 1 Bathroom, Sleeps 4
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$338
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2 Bedrooms, 1 Bathroom, Sleeps 6
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$3,151
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1 Bedroom, 1 Bathroom, Sleeps 2
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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About this property
This home has a unique pricing structure. While it can rent for less than 30 days, the owner prefers Monthly rentals. Because of this, this home offers substantial (25% off) Monthly Rental discounts. Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full... View all property information
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5 of 5 stars Reviewed 8 June 2011
This cottage is perfect for a couple, with occasional visitors. Walking distance to everything, away from the Duval madness, and reflecting the owner's taste, this rental is first...
5 of 5 stars Reviewed 6 March 2010
The heated pool and lush backyard foliage were the draw to this well appointed home. Parking was a nightmare, the neighbor to the right facing the house was most unpleasant. A...
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1 / 43
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
28 NIGHT MINIMUM STAY REQUIREMENT - SEABREEZE 4 Bedroom 3 Bath with Off Street Parking, Private Heated Pool, Fitness Center, Gorgeous!! A warm color scheme and meticulous design details lend an elegant tropical ambience to this spacious four bedroom, 3 bath home located in the 'Sanctuary' on the... View all property information
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4 of 5 stars Reviewed 2 May 2014
We rented Seabreeze for a month! It was in the Golf Course a gated community. It was a great home away from home. Very comfortable, stocked well. Had a few glitches with the...
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Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Ocean Views
  • Satellite TV
  • Washer
  • Waterfront
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Beautifully Renovated First Floor Studio for Two - Incredible Location in Historic Old Town Gorgeous studio apartment on the first floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street.... View all property information
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$613
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1 / 19
3 Bedrooms, 3 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool. This beautiful home is close to ocean and the... View all property information
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5 of 5 stars Reviewed 1 March 2014
This three bedroom condo (two upstairs bedrooms with king and twin beds and ensuite baths and a downstairs bedroom with full-sized bed and right-next-door half-bath) exceeded all...
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$315
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1 / 10
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Gym
  • 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. Bright, tropical colors and tile floors provide an island ambience to this... View all property information
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4 of 5 stars Reviewed 28 February 2014
This unit has recently been refreshed and is very comfortable. It has everything you need to have a perfect vacation. The kitchen is well stocked, if you are inclined to do some...
5 of 5 stars Reviewed 9 March 2013
We were very happy with our condo. Everything was neat and clean. Living room furniture was outdated but would not stop from returning.
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1 / 20
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1 Bedroom, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Duval Delight is a breathtaking, newly-renovated 2-story condo located at the historic 'Cuban Club' on the 'quieter' side of world famous Duval St. This high end vacation rental features a huge 55-inch flatscreen TV in the living room and all brand new furniture including a comfy, pull-out queen... View all property information
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$270
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1 / 11
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • 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. It is an upstairs unit with 2 bedrooms and 1 Bathroom with 1 queen, 2 twins... View all property information
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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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From
$334
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1 / 32
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Paradise found reservations must begin and end on a Saturday. You feel it the moment you arrive. It's a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to discover the charm and grace of Old Key... View all property information
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5 of 5 stars Reviewed 3 January 2015
We loved our stay in Key West which was enhanced by the condo's location, views, lovely large heated pool and jacuzzi with views of Atlantic Ocean, our balcony with view of ocean...
5 of 5 stars Reviewed 31 May 2014
The vacation property is well worth the price. It's well maintain with beautiful views and perfect pool. Very spacious and quiet, perfect for a family. The condo is a 2 to 3...
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$325
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1 / 23
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2 Bedrooms, 3 Bathrooms, Sleeps 7
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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$6,932
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1 / 36
3 Bedrooms, 2 Bathrooms, Sleeps 7
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
28 NIGHT MINIMUM STAY REQUIREMENT - SOUTH STREET SERENITY Beautiful Vacation Home just steps from the Beach! This light and airy 3 bedroom, 2.5 bath home has a wraparound Bahamian Style deck and expansive French doors that lead from every ground floor room to an outdoor space. Enter the private... View all property information
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4 of 5 stars Reviewed 30 April 2014
the service we received from Carlos the property manager from south street serenity was excellent. whenever we had a question he either answered the phone or called us back...
5 of 5 stars Reviewed 7 June 2014
Von der ersten Sekunde an haben wir uns sehr wohl in diesem tollen, gemütlichen und wunderbar eingerichteten Haus gefühlt. Das Haus bietet alles, was man braucht, nein, es bietet...
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$630
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1 / 9
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
The Pineapple Cottage is tucked away and totally private, yet it is only a half a block from Duval Street. This two story 'cottage' offers a first floor bedroom that opens through french doors to the private pool and gardens. A second floor suite includes a bedroom and bath plus a seperate living... View all property information
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5 of 5 stars Reviewed 19 January 2015
My wife & I have been to Key West a few times, and this last trip we brought some first timers with us. We stayed at the Pineapple Cottage and it was amazing. It truly is a...
5 of 5 stars Reviewed 29 January 2014
This place is amazing. I have been to Key West numerous times and it is rare to find a place so perfectly located in the Old Town area that also has the privacy and feeling of...
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$161
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1 / 29
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Studio, 1 Bathroom, Sleeps 2
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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
This wonderful unit is set apart from the others with cathedral ceilings and a skylight in each room; light and airy and yet very cozy and comfortable. This efficiency condo is perfect for 2 and can even accommodate the occasional guest with the living room sleeper sofa. The bedroom has a... View all property information
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3 of 5 stars Reviewed 8 October 2014
The place was pretty decent overall however it is not in the safest feeling part of town. We learned that it is right next to public housing and there are some loud neighbors at...
2 of 5 stars Reviewed 21 August 2014
The property was cute, but the surrounding areas are quite scary. The pool is a few blocks away... No Wi-Fi. The location is quite convenient and the suite was rather clean...
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From
$338
Per Night
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1 / 30
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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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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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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From
$450
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1 / 27
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
SeaShadows is a townhouse located just 2 blocks from Duval Street and a few minutes walk from Mallory Square. Down the street is Ft. Zachary Taylor Park where you can spend the day fishing, swimming, barbecuing, walking, and anything else that you can think of doing in the sun. It sleeps 4... View all property information
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5 of 5 stars Reviewed 1 July 2013
The house was very nice and well kept and within walking distance to just about anything. We did a lot of walking and actually ate in most of our meals.
5 of 5 stars Reviewed 26 May 2013
An absolutely fantastic holiday home away from home. The cleanliness of the house is an absolute joy, and there is every household amenity to make your stay comfortable. It is...
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$262
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1 / 28
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2 Bedrooms, 1 Bathroom, Sleeps 4
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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 12 December 2014
The condo was great. The place was clean, comfortable, and 1/2 block from Duval Street. We were able to walk everywhere we needed to go. There was a porch off of one of the...
3 of 5 stars Reviewed 1 October 2014
If you don't mind the Anchors away people hanging out around your bedroom porch all hours of the night, or the people up stairs playing basketball at 430 in the morning, you...
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From
$199
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1 / 27
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • 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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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...
3 of 5 stars Reviewed 6 October 2014
At the south end of Duval St 4 blocks from southern most end of US. Next door to Key West Pub, great music and Amy the bartender is super great. Across the street is Latte another...
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1 / 12
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
******** Key West laws state that this property can only be rented out monthly******* This lovely home is in the Casa Marina District of Key West. It has a front porch, front balcony that the 2 smaller bedrooms have access to, a large patio by the heated private pool in the back yard, and a... View all property information
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$338
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1 / 26
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • 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
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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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...
5 of 5 stars Reviewed 15 January 2015
Would recommend new sofa bed. A little uncomfortable and the head slopes down. We actually went out and bought a air mattress. Loved the Hot tub! We didn't care for the cat...
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$237
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Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • 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
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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$174
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1 / 25
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Studio, 1 Bathroom, Sleeps 2
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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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$473
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1 / 9
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50', 42', and 27' flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home... View all property information
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5 of 5 stars Reviewed 29 May 2013
Hemingway's Retreat was more than we could have hoped for! The house was beautiful, the location was perfect, and the pool was awesome for our family. The owner was fantastic to...
5 of 5 stars Reviewed 4 January 2013
Recently I spent a month at the property. It was well taken care of and Mark was very responsive to our needs. The home was well set up and then some. The pool is very private and...
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From
$161
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1 / 28
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Studio, 1 Bathroom, Sleeps 2
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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
This wonderful unit that has been completely remodeled in July 2013 has a private entrance in to the quaint efficiency on the back side of the complex. Featuring hardwood floors, Dade County Pine walls and a high-end, fully stocked kitchenette, this secluded hideaway offers the finest of... View all property information
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4 of 5 stars Reviewed 15 July 2014
Coral Cove was a great place to stay for 2 people. We only stayed for one night, which was just enough. It was a little cramped, but was a safe and comfortable place to sleep. It...
2 of 5 stars Reviewed 2 June 2014
We stayed for 3 nights. Yes it's small, but tiny describes it better. I have never had back problems with all the traveling I've done, until now. The worst bed. Extremely cheap...
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From
$338
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1 / 33
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2 Bedrooms, 3 Bathrooms, Sleeps 6
Details 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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From
$378
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1 / 22
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Recently renovated, two bedroom, one bathroom, high end kitchen, luxurious living room, and balcony over looking garden restaurant. Tile throughout, modern kitchen, top-of-the-line appliances, are just a few nice features of this perfect vacation rental. Just moments from some of the best dinning... View all property information
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4 of 5 stars Reviewed 9 April 2014
Just got back from Key West and this condo is in a prime location on Duval St. It is towards the back so noise is not a problem-other than roosters crowing (they are all over the...
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From
$174
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1 / 24
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Studio, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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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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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$338
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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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
  • ?
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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 opens to the living room,... View all property information
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3 of 5 stars Reviewed 20 January 2015
Overall was okay. Some details that were lacking made the stay not quite as good as expected for the cost. TV was small. Guest BR bed was not comfortable. There was mold on...
5 of 5 stars Reviewed 2 November 2013
Very attractive, well located, and with so many nice little extras. The managers are attentive and very helpful. It's easy to tell that a lot of thought and care go into keeping...
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$347
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the... View all property information
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3 of 5 stars Reviewed 4 September 2013
Our first night I was kept up until 4 AM by noisy you people and I love to hang and have fun but come on they were really poorly behaved. The following night Saturday of Labor Day...
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$440
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Ocean Views
  • Shared Outdoor Pool...
  • Washer
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
FOR INSTANT PRICING, go to KeyWestYachtandBreakfast.com. Most nights require 3 night minimum but email or call us if you want less and we can negotiate a fair rate. Upscale 'Yacht and Breakfast'! 3 bedroom, 4 bed, 2ba luxury yacht. Fully equipped from bow to stern -- Galley (kitchen to the... View all property information
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5 of 5 stars Reviewed 13 January 2015
It never crossed my mind to look into staying on a Yacht in Key West. Now, everywhere we travel it is our first option. The boat accommodations were perfect for us. We could fish...
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$275
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2 Bedrooms, 1 Bathroom, Sleeps 6
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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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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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$514
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3 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
POOLSIDE PARADISE is made up of POOLSIDE RETREAT and POOLSIDE SUITE With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens, this historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living... View all property information
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3 of 5 stars Reviewed 27 December 2014
The location is perfect--a block off Duval and 4 blocks from a grocery store. The two connected houses are somewhat run down but adequate and probably typical for "Old Town" Key...
5 of 5 stars Reviewed 6 December 2014
Poolside Paradise was the perfect place to call home during our stay in Key West and completely met our expectations. The two homes and pool were beautifully kept and staged for...
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From
$476
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • 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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3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
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  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
NEW ONE OF A KIND UNIT! To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water's edge has been quintessentially transformed into Old... View all property information
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$315
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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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5 of 5 stars Reviewed 1 January 2014
Really enjoyed staying at Shelleys Rooftop. Far enough down Duval St. to be away from the crowds but just a walk away to the crowds and popular bars. Spent Christmas with...
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From
$324
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This 2 bedroom, 1 and ½ bath end unit town home is located on President's walk ( Ivory Coast) in the prettiest section of the Truman Annex. The home is decorated in exceptional taste; including a King size bed in the master bedroom with ample closet space and its own private covered deck for your... View all property information
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5 of 5 stars Reviewed 13 January 2015
This is a wonderful place to stay in a perfect location! Just 2 blocks from Duval street and just down from Mallory Square! Its a Hidden treasure! close to everything! It was...
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$174
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Studio, 1 Bathroom, Sleeps 4
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  • 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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Studio, 1 Bathroom, Sleeps 2
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  • Air Conditioning
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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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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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This beautiful home offers you contemporary luxury combined with exquisite historical charm of Old Town Key West. The open and spacious downstairs floorplan has an abundance of natural light and opens onto a fabulous pool area with an expansive deck. Entertaining your family and friends is... View all property information
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5 of 5 stars Reviewed 3 November 2013
I was there with my husband. The place is so beautiful. It has everything you need for a great holiday. The house is spacious. The pool/garden area is very big and private. The...
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$237
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1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
AUDUBON'S LIVING ROOM HAS JUST BEEN REFURBISHED WITH NEW FURNITURE INCLUDING NEW CHAIRS AND A NEW QUEEN SLEEPER SOFA! The Audubon House is an historic free-standing one bedroom cottage featuring all the comforts of home, and more! The spacious, beautifully furnished great room features a... View all property information
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5 of 5 stars Reviewed 9 December 2014
The home was clean, centrally located. Also, safe. will be coming back and using you guys again on our next trip to key west!
4 of 5 stars Reviewed 21 November 2014
We booked here for one night because of the location. This worked out well for 2 couples - one private bedroom with full bath and separate entrance, one pull-out sofa bed with a...
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Elder access
  • ?
  • ?
About this property
Welcome to Artist House: a 2 bedroom 2.5 bath rooftop townhome located within the gated community of Duval Square. Beautifully decorated with bright colors and unique art work, this property will give you a great Key West experience and is perfectly located so that you can park your car in the... View all property information
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5 of 5 stars Reviewed 11 November 2014
My husband and I have rented this unit twice now and it is the perfect place. The rental company is wonderful to work with try to get you in to the unit early if possible. This...
4 of 5 stars Reviewed 6 August 2014
Nice condo right on duval st. Good location for a more quiet stay.Cvs right around the corner Rooms where nice. Hot tub on patio is a plus. Only negative comment is I wish we...
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$325
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2 Bedrooms, 1 Bathroom, Sleeps 6
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  • 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
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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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...
5 of 5 stars Reviewed 28 March 2014
Leeward Isle is a great place to stay for a trip to Key West. It is within walking distance to all the hot spots and to the beautiful sunsets at Mallory Square, yet far enough...
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$212
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Internet Access
  • 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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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...
5 of 5 stars Reviewed 14 October 2014
This cute little upstairs apartment was a great place to fix a quick breakfast & have coffee on the covered balcony before heading off to explore historical Old Town. The place...
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4 Bedrooms, 4 Bathrooms, Sleeps 10
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Elder access
  • x
  • ?
About this property
This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is... View all property information
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Air Conditioning
  • 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
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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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Internet Access
  • 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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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...
4 of 5 stars Reviewed 22 January 2015
We had a good time and the place was as expected based on pictures and comments from other guests. There is no stove and the sleeper sofa is appropriate for children but could not...
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$514
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • 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
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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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Hot Tub
  • 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 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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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...
5 of 5 stars Reviewed 2 May 2014
My husband and I spent 10 nights at Heron Hideaway in celebration of our 20th anniversary. Every thing that we needed was provided in this very clean and ideally located home...
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Pets allowed
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About this property
This is a lovely 3rd floor partial ocean-view unit. You will love the spacious 50 ft private balcony that runs the length of the unit. The unit is tiled throughout with a full size fully equipped eat in Kitchen. There is also a full size washer dryer for your convenience. Both bedrooms and the... View all property information
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Holiday Rental Accommodation on Key West

The diversity of the holiday rental accommodation available on Key West means that there is something available to suit every budget and surely all tastes. From cottages and modest condos, to villas and townhouses, to penthouses and country estates, Key West has it all, meaning that your holiday in Key West can be as free of restriction as possible, at a price you can afford. If you want the freedom to explore Key West at a time and in a manner of your choosing, selecting the holiday rental best suited to your individual requirements is the way to achieve your goal.

Water sports in Key West

The weather and geography of Key West make it an ideal location for a great many different types of water sports. Fishermen of all disciplines can choose from the art of fly fishing for tarpon, to deep sea fishing expeditions from a boat and most options in between. Those simply interested in being out on the water can go pleasure cruising on a charter boat, perhaps to view the dolphins and other marine life, hire a kayak and meander through the waterways at their own pace, or even jump on a jet ski and enjoy some high speed thrills. Scuba divers can admire the natural coral reefs or explore the wrecks in the area, some of which were deliberately sunk to form artificial reefs.

Popular attractions in Key West

The beaches of Key West are both numerous and beautiful but a visit to the Fort Zachary Taylor State Park allows you to combine your beach relaxation and activities with an inexpensive tour of the fort, or perhaps a casual stroll along one of the nature trails. Art lovers will find a great many galleries of interest in Key West, with the majority local to the popular Duval Street part of town. Key West Golf Club is not only about allowing golf lovers to practise their swing, it also has a popular restaurant and bar, which could perhaps serve as a point at which non-golfers can arrange to meet players after their round. One monument not to miss in Key West is the small round landmark which denotes the most southerly part of the continental United States.

Restaurants and bars in Key West

Duval Street is the popular centre of Key West in so many ways, not least when it comes to restaurants. When you are eating out from your Key West holiday rental of an evening, you may wish to sample popular outlets such as Nine One Five or Mangoes, or try the Banana Café for breakfast or lunch. Blue Heaven in the Bahama Village is the place to sample outdoor dining of the highest quality, with an indoor option available if preferred. The bars and clubs of Key West are plentiful in the extreme, with options to suit all tastes and requirements and allow you to party the night away in style.