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Rentals for Seniors in Key West, FL

71 Matching Rentals in Key West
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$186
/ Night
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1 / 21
5 of 5 stars (1) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Reviews (1) Make Inquiry
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$359
/ Night
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1 / 22
5 of 5 stars (23) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 5
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$199
/ Night
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1 / 14
5 of 5 stars (13) Excellent
2 Bedrooms / 1 Bathroom / Sleeps 6
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$195
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1 / 14
5 of 5 stars (42) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 6
travelers have booked this property
Overview Reviews (42) Make Inquiry
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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$290
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1 / 26
5 of 5 stars (14) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 6
travelers have booked this property
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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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From
$500
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1 / 23
3 Bedrooms / 2 Bathrooms / Sleeps 8
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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
  • ?
  • Wheelchair access
  • Elder access
About this property
Waterfront Condominium with 3 bedrooms, 2 bathrooms, sleeps 6 Your spacious oceanfront balcony will be a front row seat for a panorama of azure blue ocean and sky. With direct views of the ocean from the living room, master bedroom and your own private balcony, you will never want to leave this... View all property information
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From
$200
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1 / 27
5 of 5 stars (35) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 6
travelers have booked this property
Overview 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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$209
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1 / 17
5 of 5 stars (9) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 5
travelers have booked this property
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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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1 / 14
4.5 of 5 stars (16) Very good
2 Bedrooms / 2 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
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This weekly (minimum) condo is in a perfect location for enjoying all the sights of Old Town Key West - a car is not even necessary as you can walk to everything! Fly in to Key West or take the Keys Shuttle from the Miami or Ft. Lauderdale airports. This rare condominium with a second full bath... View all property information
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5 of 5 stars Reviewed August 19, 2014
Upon arrival we found condo clean and prepared for us. Location is excellent: 2 min to Duval Street, 15 min to Mallory square, 3 min ride or 10 min walk to Fort Zachary State Park...
5 of 5 stars Reviewed October 28, 2013
Drove from Co.,parked our car in assigned parking and rented bikes(The Bike Shop) for the whole week! Biking the side streets was so easy and we were very close , walking...
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From
$100
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1 / 27
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Make Inquiry
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
$400
/ Night
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1 / 6
2 Bedrooms / 2 Bathrooms / Sleeps 8
Overview Make Inquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Private Outdoor...
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Please note. This is a timeshare rental and I have only 1 week allotted to me. Please do not request any dates other than available week of March 8th through the 15th. This Hyatt property is a 2 floor--2 Bedroom Caribbean furnished condo type unit situated right in the heart of Key West facing... View all property information
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From
$250
/ Night
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1 / 15
5 of 5 stars (1) Excellent
2 Bedrooms / 3 Bathrooms / Sleeps 6
travelers have booked this property
Overview 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
/ Night
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1 / 20
4 of 5 stars (4) Very good
2 Bedrooms / 2 Bathrooms / Sleeps 6
travelers have booked this property
Overview Reviews (4) Make Inquiry
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
$149
/ Night
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1 / 20
5 of 5 stars (10) Excellent
1 Bedroom / 1 Bathroom / Sleeps 4
travelers have booked this property
Overview Reviews (10) Make Inquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Please find me elsewhere on the internet by searching for The Jungle Breeze Condo. People have been receiving the wrong quote on my property from FlipKey due to glitches in their software; the problem has been reported but I find the response time to be slow. The Jungle Breeze condo at LaBrisa... View all property information
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5 of 5 stars Reviewed October 14, 2014
My wife and I stayed here from Oct 4th thru the 11th. The Condo is situated minutes away from the airport so it was a quick taxi ride. The grounds of the complex are well taken...
5 of 5 stars Reviewed August 11, 2014
My wife, 2 adult daughters, and I, stayed at Pam's La Brisa "Jungle Breeze" condo from August 2 - 9, 2014. The condo is located in a very safe and friendly gated community. Pam...
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From
$265
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1 / 32
4.5 of 5 stars (5) Very good
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Reviews (5) Make Inquiry
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 January 2, 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 May 30, 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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From
$275
/ Night
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1 / 26
5 of 5 stars (27) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 6
travelers have booked this property
Overview Reviews (27) Make Inquiry
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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$298
/ Night
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1 / 10
3 Bedrooms / 2 Bathrooms / Sleeps 6
travelers have booked this property
Overview Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
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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From
$1,500
/ Week
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1 / 4
2 Bedrooms / 2 Bathrooms / Sleeps 6
travelers have booked this property
Overview Make Inquiry
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
$198
/ Night
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1 / 10
5 of 5 stars (3) Excellent
1 Bedroom / 1 Bathroom / Sleeps 6
travelers have booked this property
Overview Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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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From
$83
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1 / 34
Studio / 1 Bathroom / Sleeps 2
Overview Make Inquiry
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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From
$220
/ Night
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1 / 17
5 of 5 stars (2) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Satellite TV
  • Sauna
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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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$225
/ Night
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1 / 14
4 of 5 stars (12) Very good
2 Bedrooms / 2 Bathrooms / Sleeps 6
travelers have booked this property
Overview Reviews (12) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
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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From
$189
/ Night
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1 / 13
4.5 of 5 stars (5) Very good
1 Bedroom / 1 Bathroom / Sleeps 4
travelers have booked this property
Overview Reviews (5) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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
/ Night
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1 / 9
4.5 of 5 stars (14) Very good
2 Bedrooms / 2 Bathrooms / Sleeps 6
travelers have booked this property
Overview Reviews (14) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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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1 / 23
4.5 of 5 stars (14) Very good
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Reviews (14) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • 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
Two bedrooms, two and a half baths, Foundry Condo 121 Front Street in the Truman Annex, is located in the heart of Key West's Old Town. Fly in and take a taxi from the Key West airport or the Keys Shuttle from the Miami or Ft. Lauderdale airports. One reserved vehicle parking space. Available... View all property information
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5 of 5 stars Reviewed May 20, 2014
My husband & I, along with another couple, rented this condo for a week in May 2014. We found the condo to be larger than expected & quite comfortable for 4 adults. Living area...
5 of 5 stars Reviewed August 21, 2011
We had a great time staying at the Foundry Unit 6. The unit is very well decorated and has everything you need, it almost feels like if you are at home. Dave Lewis is wonderful to...
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$495
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1 / 18
3.5 of 5 stars (10) Average
4 Bedrooms / 4 Bathrooms / Sleeps 12
travelers have booked this property
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
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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From
$300
/ Night
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1 / 23
3 Bedrooms / 2 Bathrooms / Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
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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From
$2,650
/ Week
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1 / 12
2 Bedrooms / 3 Bathrooms / Sleeps 6
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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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1 / 18
2 Bedrooms / 2 Bathrooms / Sleeps 6
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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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1 / 37
4 of 5 stars (1) Very good
1 Bedroom / 1 Bathroom / Sleeps 2
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  • Pets allowed
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  • Suitable for children
  • x
  • x
  • x
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  • x
About this property
This vacation home is only licensed for stays of 28 nights or more. Southard Square Hideaway is a newly renovated first floor corner condo perfect for 2 plus space for visiting friends and family! Monthly Rental A surprise awaits you inside the gates of the Southard Square village. Nestled in the... View all property information
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1 / 35
3 Bedrooms / 2 Bathrooms / Sleeps 8
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  • Air Conditioning
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  • Hot Tub
  • Internet Access
  • Ocean Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
One of the very few & one of the largest oceanfront suites in Key West OCEANFRONT… there is nothing like it. To me, it means being directly on the shoreline with nothing between me and the sensation of the ocean. Totally different from ocean view, which could mean having to lean over your balcony... View all property information
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1 / 20
2 Bedrooms / 2 Bathrooms / Sleeps 6
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • 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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4.5 of 5 stars (7) Very good
3 Bedrooms / 2 Bathrooms / Sleeps 6
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  • Pets allowed
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  • Suitable for children
  • x
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About this property
Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
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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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1 / 10
4.5 of 5 stars (6) Very good
2 Bedrooms / 2 Bathrooms / Sleeps 5
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  • Dryer
  • Gym
  • Hot Tub
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  • Washer
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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 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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4 of 5 stars (1) Very good
4 Bedrooms / 3 Bathrooms / Sleeps 8
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  • Air Conditioning
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  • Dryer
  • Grill
  • Gym
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  • Private Outdoor...
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • 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 May 1, 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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1 / 19
5 of 5 stars (9) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 6
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  • Washer
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Envision yourself unwinding and getting into the casual clothes we wear in Key West while you look around and know you are in Paradise as our island is called. Then ask anyone and they will tell you the best place to stay in Key West is the Truman Annex. My Bermuda-style cottage is on the... View all property information
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5 of 5 stars Reviewed September 4, 2014
After several visits to KW, this was our second time staying in a condo in Truman Annex. We were situated right on Southard Street, and sat on our porch enjoying a festive parade...
4 of 5 stars Reviewed August 24, 2014
This was our first visit to Key West and we stayed here with our 3 kids. While we could have walked to the beach, we drove anyway and it took about 3 minutes. The walk to Duval...
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1 / 11
5 of 5 stars (2) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 6
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
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  • Elder access
About this property
The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
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5 of 5 stars Reviewed March 22, 2014
A great condo. All the amenities. Covered parking, close to the pool. Easy access to downtown, either by car or taxi. Wonderful communication with the owner. First time for 4 of...
5 of 5 stars Reviewed January 23, 2014
The condo was fantastic. I was clean convenient and would recommend to anyone. This was exactly as described.
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3 of 5 stars (1) Average
2 Bedrooms / 2 Bathrooms / Sleeps 6
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  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
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  • 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 September 3, 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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1 / 19
3 Bedrooms / 2 Bathrooms / Sleeps 6
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  • Waterfront
  • Water Views
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  • Suitable for children
  • x
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  • Elder access
  • ?
About this property
BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach ,... View all property information
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1 / 18
5 of 5 stars (1) Excellent
3 Bedrooms / 2 Bathrooms / Sleeps 8
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  • Air Conditioning
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  • 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 January 12, 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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1 / 11
1 Bedroom / 1 Bathroom / Sleeps 4
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Tropical oasis in the heart of key west. Historic landmark 1 block from duval street. Walk to the pier for sunset celebrations, artists, musicians and entertainment. Surrounded by restaurants and shops and key wests popular theatre. Mel fishers museum is just down the street. Enjoy bicycles,... View all property information
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1 / 7
2 Bedrooms / 2 Bathrooms / Sleeps 6
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  • Air Conditioning
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  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This stunning 2 bedroom/2 bath suite can accommodate up to 6 guests. Whether you want the hustle and bustle of Key West or just want to kick back and relax, this resort has it all. View all property information
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1 / 17
4 of 5 stars (2) Very good
4 Bedrooms / 2 Bathrooms / Sleeps 8
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  • Air Conditioning
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  • Dryer
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  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
SEE 'RATES' FOR SPECIAL OFFER OVERVIEW The Main House is a (2) story 100+ year old, recently completely renovated Conch house. The design of this property lends itself perfectly to small gatherings of families and friends. The house can comfortably accommodate a maximum of eight (8) guests - (1)... View all property information
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4 of 5 stars Reviewed July 11, 2014
This property is lovely. With the large main house and several small cottages,it would be great for family reunions. The pool, jacuzzis and landscaping are all beautifully...
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1 / 7
5 of 5 stars (1) Excellent
7 Bedrooms / 6 Bathrooms / Sleeps 18
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  • Air Conditioning
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  • 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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$140
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1 Bedroom / 1 Bathroom / Sleeps 4
traveler have booked this property
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  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! The property is completely private and safe, surrounded by a 6 foot gated fence and tropical landscaping. Due to local zoning laws we... View all property information
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$200
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1 / 14
5 of 5 stars (8) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 6
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  • x
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About this property
Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two blocks from Duval Street, home of world famous watering holes, shopping and dining, you are steps away from Faustos grocery, Sandy's Café for the best... View all property information
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4 of 5 stars Reviewed April 23, 2012
We've stayed in 4 different vacation rentals for a month or more at a time, and I think we enjoyed Casa Manana the best. Lots of character, great location, friendly cats and...
5 of 5 stars Reviewed July 2, 2011
The home was wonderful & the perfect size for our family. It was close to everything & we enjoyed the nearby church bells while sitting by the pool. We were surprised however...
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$195
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4.5 of 5 stars (15) Very good
2 Bedrooms / 2 Bathrooms / Sleeps 6
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  • Air Conditioning
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  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
2 Bedroom 2 bath Island view condo located in the oceanfront condominium complex with the largest oceanfront pool & 20 person hot tub. Sleeps 4-6. Everything you need for an island vacation without the cramped hotel room! Outdoor balcony access from living and bedroom areas. Fully equipped kitchen.... View all property information
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5 of 5 stars Reviewed November 1, 2014
You name it, the condo had it. Plenty of bath towels. Beach towels and water toys. ironing board, cooking utensils, even some books to read. TVs in living room and both bedrooms...
5 of 5 stars Reviewed October 7, 2014
This condo is very spacious and was amazingly well supplied with beach towels, picnic basket, beach chairs, iron, utensils, beach toys etc. Compared to a lot of other condos I...
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1 / 10
5 of 5 stars (3) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 6
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  • Pets allowed
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  • Suitable for children
  • x
  • x
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  • ?
About this property
Unit C232 is one of the premium rental Condo's in the 1800 Atlantic Complex. Beautifully decorated with higher end furnishings. Top of the line full size fully equipped eat in Kitchen. Dining room area and spacious living room. Both Bedrooms and the living room open onto the expansive private... View all property information
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5 of 5 stars Reviewed January 2, 2012
We had an enjoyable experience from the time we arrived at 1800 Atlantic until we left. The nice security guard on duty on Sunday night couldn't have been more helpful. The unit...
5 of 5 stars Reviewed July 15, 2010
Every facet of our stay was perfect. We have stayed in many other places in Key West, and this is by far our favorite! We have stayed in this particular unit several times, and...
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1 / 8
5 of 5 stars (1) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 6
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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About this property
2 bedroom 2 bath top floor ocean-view condo at 1800 Atlantic. This unit has been totally renovated and no attention to detail spared. The Master Bedroom has king bed, The guest bedroom has a queen and the living room has a queen pull-out sleeper sofa. High speed interent available. There is a... View all property information
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5 of 5 stars Reviewed September 9, 2010
The condo we stayed in had obviously been remodeled. It was gorgeous with plenty of space for 4 people! Also, the pool and jacuzzi were huge! We really enjoyed the accomodations...
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5 of 5 stars (25) Excellent
2 Bedrooms / 2 Bathrooms / Sleeps 5
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Key West Vacation Rentals 2 Bed 2 Bath Condos On The Ocean with ocean and partial ocean views - rent weekly or nightly. To see both my condos on my website with active availability calendars and virtual tours - Click on my name 'Henry Karp' - just to the right of this paragraph then scroll down... View all property information
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5 of 5 stars Reviewed July 23, 2014
This was a great place to stay with my husband and four teenage kids. We all had plenty of room as the rooms were huge...even the bathrooms! Everything we needed was there...even...
5 of 5 stars Reviewed March 12, 2014
This was our first trip to Key West and after staying at Henry's we will be back next year! Everything is perfectly laid out for you by Henry before you get there! The Condo is...
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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.