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Vacation Rentals in Key West, FL

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$186
Per Night
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1 / 21
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$249
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1 / 14
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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$359
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1 / 22
2 Bedrooms, 2 Bathrooms, Sleeps 5
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$199
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1 / 14
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2 Bedrooms, 1 Bathroom, Sleeps 6
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  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
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  • Elder access
  • x
About this property
Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West... View all property information
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5 of 5 stars Reviewed November 18, 2014
We were in key west playing music at a friend's wedding around the corner at old town manor. The Bahama House is perfect! it is close to everything, there's a beautiful pool...
5 of 5 stars Reviewed August 21, 2014
What an amazing location! Just half a block from Faustos market and one block from the Trolley stop. Could not have planned that any better. One of our group members had walking...
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$195
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1 / 14
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Gym
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The... View all property information
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5 of 5 stars Reviewed January 18, 2015
The accommodations were awesome. Very clean and updated with all the feeling of a home away from home. Communication with owners was excellent and we truly enjoyed our stay...
4 of 5 stars Reviewed January 17, 2015
Our 4 days staying at the Tropical Escape condo were great! It was comfortable, clean and had everything we needed. The pool and hot tub were warm and lovely. The owners of...
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$138
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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 January 16, 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 November 17, 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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$229
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1 / 17
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2 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an... View all property information
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5 of 5 stars Reviewed January 28, 2015
Loved the house, pool, location. Beds were very comfortable. Loved everything about it. Already have friends asking about rental.
5 of 5 stars Reviewed January 15, 2015
We were so pleased with this accommodation. The location is fantastic for enjoying all that Duval Street has to offer. Would recommend this place to anyone. Just sorry our...
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$290
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1 / 26
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Ocean Views
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
************************************************************************************************* TAKE 25% OFF: -- Stay March 1-4 (3 nights) and pay $355/night instead of $475/night. -- Stay April 4-6 (2 nights) and pay a reduced rate of $765 for both nights instead of $1,025. -- Stay April 11-14... View all property information
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5 of 5 stars Reviewed December 7, 2014
All the previous reviews are completely accurate. The location is quiet and peaceful but only minutes away (by car) from Duval Street. Inside, the condo is very well-appointed...
5 of 5 stars Reviewed November 2, 2014
This two bedroom condo has everything! Beautiful views, beautiful decor, incredibly clean and comfortable and equipped with everything you could want. We stayed for four days and...
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$138
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1 / 28
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Studio, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
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 October 29, 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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$200
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1 / 27
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (35) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This is a non-smoking condo (smoking on the balcony only) with that 'home away from home' appeal. My condo is reasonably priced and includes 1 king bed suite and 1 queen bed suite and a sofabed. All bed linens are provided. Wait there is more, 2 full baths, fully equipped kitchen (dine in/dine... View all property information
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5 of 5 stars Reviewed January 8, 2015
We have been going to Key West for 8-9 day stays for 20 years. Stayed in lots of rentals but this has been by far the best accomadations we've have had. It had the comforting...
5 of 5 stars Reviewed December 31, 2014
Fanatastic location. Perfectly appointed with every amenity. Immaculate. Pool was wonderful. Pam was very helpful. We had an amazing holiday away from home in a Pam's...
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From
$1,700
Per Week
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1 / 26
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
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5 of 5 stars Reviewed January 18, 2015
Recently spent one week at Casa del Sol. This rental was in a perfect location, wonderful amenities, tastefully decorated and as neat as a pin. The Truman Annex location was...
5 of 5 stars Reviewed July 31, 2014
Great rental, right in the middle of everything. We arrived and everything was as described. Wifi was a great bonus for teenage son. House clean and tidy with plenty of linen...
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$209
Per Night
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1 / 17
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street. Completely updated for your comfort and convience with new furnitire,... View all property information
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5 of 5 stars Reviewed December 28, 2014
I stayed there for my 60 th birthday celebration and enjoyed all the features tremendously, had a wonderful stay, really did not want to leave. Owners were always available to...
5 of 5 stars Reviewed November 28, 2014
If you want to be in the heart of all the Key West action and at the same time have all the comforts of home (living room, two bedrooms with comfortable beds, two full baths...
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From
$800
Per Night
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1 / 29
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4 Bedrooms, 4 Bathrooms, Sleeps 10
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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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From
$100
Per Night
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1 / 27
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 28 nights*** Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light and bright colors. There is a King bed in the master and a queen in... View all property information
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From
$138
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1 / 26
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Studio, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Part of Southernmost Suites The Pelican Suite is located in The Southernmost Suites on historic Simonton Street. Tucked back within the garden the Spoonbill Suite offers a serene escape from the hustle and bustle. The Pelican Suite has 2 Queen Beds and a kitchenette for you to enjoy meals in... View all property information
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From
$4,000
Per Month
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1 / 14
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2 Bedrooms, 5 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Private Outdoor...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
MONTHLY RENTAL ONLY Buoy's Backyard - an authentic Key West retreat in the historic district just a block from upper Duval (the quiet end), two blocks from Hemingway House, and three blocks to Southernmost Buoy and Beach. Brick driveway provides private gated parking for two cars. This home has... View all property information
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From
$250
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1 / 15
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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Details Reviews (1) Make Inquiry
Amenities & Details
  • 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 December 31, 2013
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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$225
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1 / 20
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
Come down and take part in in Key West's many fishing tournaments this summer! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family... View all property information
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2 of 5 stars Reviewed April 15, 2014
We certainly did not get what we thought we were paying for. WiFi was virtually non-existent. The "fully-equipped" kitchen had no serving spoons, only two dish towels, and ants...
5 of 5 stars Reviewed February 10, 2014
I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
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From
$139
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1 / 21
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1 Bedroom, 4 Bathrooms, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Pool Table
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Beautiful New large modern Home on very quiet street . Location , Location Location ! Share .5 Star $2.4m Home in Old Town Key West.. Own fully furnished bedroom with Queen size bed for 1 - 2 max ( see photos ) with large flat screen t.v. and 2 french doors leading onto private balcony... View all property information
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5 of 5 stars Reviewed January 12, 2015
Don is very attentive to the needs of his guests. Beautifull house. You have access to a little paradise in his backyard: warm water pool, jacuzzi, BBQ, even a living room pool...
5 of 5 stars Reviewed November 15, 2014
This house was great!!! Don was not only a gracious host but absolutely funny. House is EXACTLY as pictures online show, but better. The location for us was perfect as it was...
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From
$128
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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 October 7, 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 August 20, 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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$275
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1 / 26
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is oceanfront with an Olympic... View all property information
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5 of 5 stars Reviewed December 15, 2014
We stayed in the condo for four nights with five people and we were all pleasantly surprised to see how well equipped the condo was. The condo has two bedrooms and though we could...
5 of 5 stars Reviewed November 30, 2014
We (my wife, her mother, our 10 and 13 year old boys) had a great stay. Well equipped kitchen, bikes to use during our stay, comfortable for the five of us, good location. The...
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From
$395
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1 / 9
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3 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
1207 Heaven is Key West Casual at it's best! Decorated by a world travelling, gallery Curator/Artist/Entrepreneur- the place is a refreshing twist of elegant, sophisticated & funky with local & international art, contemporary & mid-century modern decor & comfort. The layout includes 2 bedrooms &... View all property information
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$1,500
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1 / 6
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1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a 'closet... View all property information
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$1,500
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1 / 6
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2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge... View all property information
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From
$128
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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 July 14, 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 June 2, 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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$1,500
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1 / 4
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping.... View all property information
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From
$450
Per Night
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1 / 15
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
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5 of 5 stars Reviewed December 29, 2014
The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
3 of 5 stars Reviewed December 28, 2014
Place needed a remodel. looked like from 70's Asian condo. Too many mirrors in the place and red ants in the master bedroom. We couldn't cook as the frying pans were so old and...
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From
$1,200
Per Night
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1 / 7
7 Bedrooms, 6 Bathrooms, Sleeps 18
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Our unique property consists of 3 suites (a total of 7 bedrooms and 6 baths) with 2 sparkling lagoon style dipping pools in one compound in the luxurious Casa Marina area of Old Town Key West. We can accommodate groups up to 18 guests. The breakdown of the 3 suites which are being rented... View all property information
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5 of 5 stars Reviewed February 16, 2014
So our stay was Friday - Tuesday in January … We rented the Hemingway suite then added additional rooms … Love Love Love this place !! can not say enough about the owners / and...
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From
$175
Per Night
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1 / 10
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Hot Tub
  • Internet Access
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About this property
Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
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5 of 5 stars Reviewed December 11, 2014
This condo at Sunrise at Seaside is perfect for a family vacation. We stayed there last Thanksgiving weekend and had a wonderful time. The condo is very well maintained and...
4 of 5 stars Reviewed June 9, 2014
Very good price for a 2 bed 2 bath in Key West! It Was clean and just what we needed! It was also not right in downtown close to everything so we could get away hen we wanted.
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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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About this property
The 'SeaJay' at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers... View all property information
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5 of 5 stars Reviewed May 21, 2014
We enjoyed our week in the condo immensely. I considered it a bargain compared to other vacation rentals we checked. There were 5 of us (3 generations) and there was plenty of...
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$495
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Suitable for children
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About this property
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft. on two... View all property information
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5 of 5 stars Reviewed April 17, 2014
This house was gorgeous. Clean, updated and simply beautiful. It also had everything we needed...hair dryers, ironing board, laundry room, etc. If you are looking for something...
5 of 5 stars Reviewed October 9, 2013
Six women stayed in this beautiful townhome for three nights for a girls getaway. We would normally have booked hotel rooms, but staying here far exceeded our expectations and we...
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$225
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  • Gym
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  • Smoking allowed
  • Suitable for children
  • x
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About this property
This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience... View all property information
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4 of 5 stars Reviewed January 26, 2015
We were pleasantly surprised with the condo. 2 separate bedrooms with 2 separate bathrooms and a kitchen and Living room. Bar stools for the kitchen bar. The condo was fully...
3 of 5 stars Reviewed November 16, 2014
This is a nice 2 bed 2 bath condo, clean, comfortable, and nicely decorated. The pool and hot tub in this small resort were very nice. Kitchen was adequate with new pans - I...
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$198
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1 Bedroom, 1 Bathroom, Sleeps 6
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  • Suitable for children
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About this property
The Bonaire Suite is a bi-level suite decorated in a rich contemporary Palm Tree motif with two queen beds separated by a privacy curtain in the upstairs bedroom. The upstairs bath features a custom tumbled marble shower with glass door. Downstairs is a living room with sofa which converts to a... View all property information
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5 of 5 stars Reviewed July 12, 2014
My friend and I stayed at the Bonaire Suite and it was perfect! Cute bungalow style with plenty of room and amenities. So close to Duval, but you couldn't hear the roar, which...
5 of 5 stars Reviewed June 12, 2014
Perfect location! Half block from Duval street. Very cozy and well equipped and lovely pool area. I highly recommend this place.
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1 / 8
3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Suitable for children
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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 November 3, 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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$189
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Suitable for children
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About this property
Resort style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages, amidst lush tropical landscaping, sits Island Style, the sister cottage of Hidden Treasure. One of our most popular properties, it was renovated by two fabulously funky sisters who share... View all property information
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4 of 5 stars Reviewed July 9, 2014
Nice little cottage with private patio, located adjacent to the pool. Cottage was clean and well maintained, and had a full kitchen with all the amenities. It was walking...
5 of 5 stars Reviewed December 22, 2012
Kevin, Shelby, and all the folks at KW Hideaways, I wanted to take a moment to thank you all for a wonderful experience! You and your team worked hard to ensure everything...
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$298
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Elder access
About this property
Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find Hidden Treasure. Truly a treasure, it is the sister cottage of Island Style, owned by two sisters who share a passion for Key West. It features every high end amenity that you... View all property information
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5 of 5 stars Reviewed October 28, 2014
Hidden Treasure is just that - a hidden treasure located off of Olivia street in The Colony. Lots of space including storage, a great outdoor area, a quiet secluded area and yet...
4 of 5 stars Reviewed September 11, 2014
Great location for walking and biking all around Key West. Close to restaurants and attractions. Limited Parking.
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$495
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4 Bedrooms, 4 Bathrooms, Sleeps 12
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  • Pets allowed
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  • Suitable for children
  • x
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About this property
Mermaid Cove is a small island compound that is great for large groups or big families. It's made up of 2 apartments and 2 cottages with an intimate courtyard in the middle with BBQ grill and table, shaded by a massive mango tree. Located right on Duval Street, Mermaid is just a block and a half... View all property information
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2 of 5 stars Reviewed January 8, 2015
I stayed at this property last August (booked by someone else) and have to say that it was an experience. We rented the whole property for 5 adults and the overall consensus was...
5 of 5 stars Reviewed January 2, 2015
If you want to experience Key West like the locals do, then Mermaid Cove is for you. Quaint hideaway in the midst of historic Key West close to shops and few restaurants Mermaid...
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$500
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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About this property
Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental View all property information
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$6,750
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Suitable for children
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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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3 Bedrooms, 2 Bathrooms, Sleeps 6
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WOW Oceanside Voted #1 Key West's Best Luxury Penthouse Marina/Condo/Pool Direct Oceanfront 1490 Sq Ft Condo, 3 Bedrooms, 2 Baths, (Sleeps 6) Oceanside Marina is one of the newest and one of the most prestigious communities offering breath taking water views and large, open units. The... View all property information
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$2,650
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Suitable for children
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About this property
100% Renovated in September 2013! A luxury, ocean front, 2 bedroom, (king in master, Bunk beds with lower Queen bed in 2nd Bedroom and a sleeper in living room couch) 2.5 bath condo at # 216 Harbor Place in Truman Annex in old town Key West. On the ocean behind the Little White House. Second floor... View all property information
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • ?
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About this property
Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in... View all property information
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$225
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Gym
  • Hot Tub
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool on property, perfect for sunbathing. Jacuzzi and gym. Tennis court. Small boats on trailer allowed.... View all property information
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$400
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
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  • Elder access
  • x
  • ?
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 June 7, 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 March 5, 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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About this property
Incredible resort during the 'peakest' of peak seasons in Key West, Florida. This extraordinary resort is not right in the heart of the Duval Street area, and it therefore offers the best of both worlds to visitors. Since it's within a short car or cab or scooter or bike ride from the Old Town... View all property information
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$183
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  • 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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About this property
Bluewater is a classic porch-on-porch Key West home with all the amenities to make your vacation ideal. Located in the prestigious Sanctuary of the Key West Golf Club, the house has two bedrooms each with its own private bath. The house sleeps 4 adults and two children or smaller adults. It... View all property information
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Safe
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
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  • ?
  • ?
About this property
The artist cottage is mainly used as a residence for visiting artist that are in town doing shows at my gallery. The cottage is very quiet and secluded with lots of privacy,situated amongst 100 year old trees and lush tropical foliage. The cottage was built in 1913 and is a true piece of old key... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
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  • Elder access
  • ?
  • ?
About this property
Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront condos have a range of room types to suite your... View all property information
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5 of 5 stars Reviewed September 4, 2013
We have been renting a condo at this property for many years under different mangement companies and the folks managing it now are top notch the are doing a great job
4 of 5 stars Reviewed July 31, 2013
The location was perfect for us since we had a boat and the rental came with a boat slip. Our balcony even looked down on our boat. Room space was very adequate for the eight of...
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Key West Vacation Rentals and Condos

Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!

Of course, it’s not all limes and leisure. Phenomenal water activities and outdoor recreation are just steps from your vacation rental, while kid-friendly adventure parks are abundant. The social scene on Duval Street caters to both a younger and older clientele looking to mingle over mouthwatering cuisine or tantalizing cocktails.

Condo rentals in Key West are so enticing that the island is known as the “Winter White House” because of its appeal to visiting U.S. presidents, and it’s been home to literary greats Ernest Hemingway and Tennessee Williams.

Where To Rent a Vacation Home in Key West

Vacation rentals in Key West can be found all over town, but knowing what each area offers will help you decide on the perfect place. Condo rentals in Old Town will put you in the center of the action – steps from the famous Duval Street, with numerous restaurants, bars, boutiques, souvenir shops and major attractions. Luxurious, modern house rentals on the beach offer more privacy and relaxation. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.

Many House Rentals Near Attractions and Activities For All Ages

Key West vacation rentals scatter the whole island, so you’ll always be close to family fun and adventure. Fury Water Adventures offers jet skis, kayaking, parasailing, boating and some of the best snorkeling and diving excursions you’ll ever find. Fishermen will marvel at the eclectic aquatic life in the crystal-blue waters, while families can take the kids to the Florida Keys Eco-Discovery Center, with interactive and dynamic sea exhibits – all just steps away from the island’s spacious, family-friendly condo rentals. Enjoy the romance of paradise on a sunset dinner cruise to wind down from a busy day on the beach or in town.

Key West Bars and Restaurants

Bustling nightlife and gastronomy surround the house rentals in the Historic Seaport neighborhood. Start your night with frozen daiquiris at the famous Lazy Gecko before moving to the award-winning Italian restaurant La Trattoria on the legendary Duval Street. A visit to Key West wouldn’t be complete without trying the conch fritters. And we recommend you indulge in as many different versions of key lime pie as possible. Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.

Book a Key West Vacation Rental For Your Next Trip

Vacation rentals in Key West are the perfect way to experience the island like a local. Traipse down Duval Street to take in the culture, enjoy the family-friendly attractions with your children and loved ones and relax on the white-sand beaches with a margarita in hand. Whichever way you vacation, TripAdvisor has the best deals on house rentals, condo rentals, and beach homes in Key West.