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Rentals for Seniors in Key West, FL

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$209
Per Night
1 / 15
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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$250
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1 / 15
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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$233
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1 / 12
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1 Bedroom, 1 Bathroom, Sleeps 4
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$225
Per Night
1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
Make memories the whole family will cherish in this great family friendly condo in Key West. It's close to all the major attractions on the island but far enough away that everyone can get a good night's sleep if they want. Want to go to the beach? The condo is a short drive to Smathers Beach.... 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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$268
Per Night
1 / 33
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2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (22) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and... View all property information
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5 of 5 stars Reviewed November 16, 2014
Stayed in this condo for 3 nights during Key West boat races. Check in with Key west Vacation rentals was easy, they're right on premises. Condo is above Duval Square. Very...
4 of 5 stars Reviewed October 27, 2014
This was a very nice, two-bedroom rental very near Duval and Truman in Key West. The property is well-kept, and the two-seater hot tub was nice. Our only problems were when...
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$700
Per Night
1 / 25
3 Bedrooms, 3 Bathrooms, Sleeps 7
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
NEWLY LISTED WITH PLENTY OF AVAILABILITY Key West Vacation Rental "SECRET VILLA II" A Hidden Jewel in Historic Old Town Key West Our property "SECRET VILLA" is so popular and in such high demand, the owner has purchased and remodeled the mirror image of it to create "SECRET VILLA II" Location,... View all property information
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$199
Per Night
1 / 14
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2 Bedrooms, 1 Bathroom, Sleeps 6
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Details Reviews (12) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • 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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$225
Per Night
1 / 14
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (11) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Safe
  • 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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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...
5 of 5 stars Reviewed May 6, 2014
The location was great. Very Quiet. Exactly as described. Would definitely stay here again! I was also incredibly grateful the for the quick response times to my emails.
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$175
Per Night
1 / 10
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Washer
Suitability
  • 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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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.
4 of 5 stars Reviewed May 23, 2014
Condo was a great location. Near beaches and activities. Great place to relax. Owner was very courtious. Pool was a little small but the facilities were beautiful.
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From
$250
Per Night
1 / 11
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • 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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From
$258
Per Night
1 / 36
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2 Bedrooms, 1 Bathroom, Sleeps 6
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Details Reviews (15) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Part of ALMOST SOUTHERNMOST RETREAT This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St. The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features a... View all property information
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5 of 5 stars Reviewed July 1, 2014
Our first visit to the Keys celebrating our 28th anniversary with our adult children, (3 couples) this historic cottage slept all 6 of us very comfortably; in fact, the most...
5 of 5 stars Reviewed February 4, 2014
We have stayed at this property on previous visits to Key West- it is a great location- close to everything and has plenty of space. Easy to cook at home if you don't want to go...
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$258
Per Night
1 / 31
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2 Bedrooms, 1 Bathroom, Sleeps 6
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Details Reviews (7) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
One half of the group unit Tradewinds and Opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design. The Webster Dictionary dates windward back to 1549; defined as, the side or... View all property information
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4 of 5 stars Reviewed July 21, 2014
Very nice place, beds were super comfy. Close to Duval but quiet. This place does have a parking spot, but we were not told about it until I called.
5 of 5 stars Reviewed March 24, 2014
Excellent accommodations! Slept five adults comfortably, but the one bathroom was a little rough at times. We're all friends so no big deal! Especially enjoyed the hot tub and...
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$138
Per Night
1 / 26
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Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
The Mallory Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
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5 of 5 stars Reviewed June 23, 2014
Wonderful. And 'Ive stayed here several times. We also bring our 2 yorkies I love the Mallory, the Truman. So close to everything. Room is beautiful too. And very reasonable in...
5 of 5 stars Reviewed June 18, 2014
Very clean, great location, kitchen well equipped, dog friendly, bed was comfortable, quiet location, shower a little small
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$198
Per Night
1 / 23
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Details Reviews (32) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
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 November 16, 2014
Wow, did we EVER choose the right place to stay. We went to Key West for the week for my oldest daughter to have a Destination wedding their. It was our first time going to Key...
5 of 5 stars Reviewed November 10, 2014
This is a great option for the Keys. Close to all the major attractions of the keys. Very comfortable and clean. Pam has done an amazing job and is sweetheart to talk too. We're...
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From
$289
Per Night
1 / 11
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1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
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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From
$178
Per Night
1 / 26
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1 Bedroom, 1 Bathroom, Sleeps 4
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Details Reviews (47) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Part of the Nightly Group PALM GARDENS Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details. Osprey's Nest is an upstairs spacious unit at 905 White Street. The original Dade County pine walls have been saved... View all property information
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3 of 5 stars Reviewed November 11, 2014
The Osprey Nest accommodation is very comfortable and pleasant. It's a bit of a hike from the action on Duval Street, which is good because it's in a quiet neighborhood, but a...
5 of 5 stars Reviewed August 20, 2014
We stayed here for a week in August '14. Our friends stayed at the Southernmost Hotel and spent almost $1000 more than us for a double queen room. The place is very nice. Clean...
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$178
Per Night
1 / 22
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (28) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Part of the Nightly Group PALM GARDENS Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration... View all property information
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5 of 5 stars Reviewed September 2, 2014
I stayed here this past Labor Day weekend for a friend's bachelorette party. There were 10 of us, and the Heron Hideaway as well as the three other one-bedroom condos in the area...
5 of 5 stars Reviewed May 1, 2014
My husband and I spent 10 nights at Heron Hideaway in celebration of our 20th anniversary. Every thing that we needed was provided in this very clean and ideally located home...
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$268
Per Night
1 / 25
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2 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
Details Reviews (14) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security... View all property information
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5 of 5 stars Reviewed August 21, 2014
I have stayed in this location once before. They have upgraded the flooring and it looks great. The pool is quiet and relaxing. The unit sits back from Duval Street so there is...
5 of 5 stars Reviewed August 18, 2014
Positioned right with ammeneties, beaches, and bars close by. Short stroll to any need. Place was very clean and with 2 bedrooms, 2.5 baths , pull out beds was very...
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From
$248
Per Night
1 / 29
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2 Bedrooms, 1 Bathroom, Sleeps 6
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Details Reviews (8) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location. Enjoy nearby bars,... View all property information
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5 of 5 stars Reviewed July 4, 2009
My husband and I stayed here with my parents and had a really wonderful time. The house was adorable, clean and had everything we needed. It was close to all the action on Duval...
5 of 5 stars Reviewed July 2, 2009
Great location off the upper section of Duval. Close enough to walk to everything but far enough to be quiet. Perfect size for 2 or 4 people. Clean and comfortable. Would...
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$450
Per Night
1 / 9
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
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 August 16, 2014
I came down with my family and we loved this place. We had a direct view of the water and it was amazing waking up every morning to see that. Very relaxing. Friendly people...
5 of 5 stars Reviewed May 29, 2014
This was our first trip to Key West and everything was great including the condo. Very nice view, great pool, short walk to very nice beach. What more would you want.
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$378
Per Night
1 / 34
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Private Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Part of ALMOST SOUTHERNMOST RETREAT Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of... View all property information
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5 of 5 stars Reviewed July 25, 2014
This is our second time staying in this property. We stayed here again because the property manager & his team were fantastic, the property was very clean and it was a great...
5 of 5 stars Reviewed June 6, 2014
Very clean, looks recently redone. Great set up, plenty of room for the six of us. Most comfortable bed ever. Literally steps from Duval St. I would definitely stay here again.
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$188
Per Night
1 / 27
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1 Bedroom, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (18) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located inside the Villas known as Old Town Garden Villas Little Havana suite is a bi-level suite with a very spacious bedroom upstairs with king bed, down pillows, tv/dvd player, cordless telephone, writing desk and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, a/c... View all property information
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5 of 5 stars Reviewed June 25, 2014
I can't say enough about this rental! Excellent location, very clean and the courtyard is amazingly beautiful.. You feel like you are in a private paradise on the island.. The...
5 of 5 stars Reviewed June 14, 2014
We stayed here the first week of June 2014. We were welcomed by management at the rental office, offered a cold beverage, and given an umbrella for our use. We were picked up at...
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From
$268
Per Night
1 / 31
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2 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
Details Reviews (33) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa Caribe is a second story paradise just steps from the sights, sounds and excitement of world-famous Duval Street. Lush and tropical gardens surround this beautiful... View all property information
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4 of 5 stars Reviewed November 11, 2014
Casa Caribe was a wonderful place for us to stay while in KW. It's on the quiet end of Duval so don't be deterred by the address, only a few blocks from the Southernmost point...
4 of 5 stars Reviewed July 2, 2014
Condo was in a great location, the staff was very helpful and friendly. Had one maintenance problem which was the garbage disposal and was fixed with in 24 hours. There is no...
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From
$258
Per Night
1 / 23
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2 Bedrooms, 3 Bathrooms, Sleeps 7
Details Reviews (17) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Short walk to Fort Zachary State Park and South Beach! This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private,... View all property information
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5 of 5 stars Reviewed September 27, 2014
Very, very nice! Comfortable and clean too. Only complaint is the roosters next door crowing early in the morning. Very audible on the master bedroom side of the unit.
5 of 5 stars Reviewed August 19, 2014
Traveling with a group of six people, we found Casa Bonita to be the perfect location for our stay in Key West. The property is gorgeous and incredibly well taken care of; and...
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From
$278
Per Night
1 / 13
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Housekeeping...
  • 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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From
$178
Per Night
1 / 28
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1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (20) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located inside the Villas known as Old Town Garden Villas With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door!... View all property information
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5 of 5 stars Reviewed June 26, 2014
Our stay at the Abaco Suite through Key West Vacation Rentals was near perfect. The rental company was very professional and helpful. The check-in and out was seamless. We...
4 of 5 stars Reviewed April 7, 2014
TThis is a lovely 1-bedroom townhome situated in an ideal location among 8-9 units on around a truly beautiful courtyard. First off, you really get the bang from your buck at this...
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From
$538
Per Night
1 / 31
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4 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
Details Reviews (44) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Two Queen bedrooms upstairs (each with a private bath) and two Queen bedrooms downstairs (each with a private bath) gives sleeping privacy and convenience for up to 8. Each bedroom has flat screen TVs, air-conditioning and ceiling fan. The two upstairs bedrooms have showers, the two downstairs... View all property information
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5 of 5 stars Reviewed November 17, 2014
Beautiful home with outstanding service. Every little detail was perfect. There were 6 of us and this large 4 bedroom, 4 Bath rental unit was incredible. The Key West Vacation...
4 of 5 stars Reviewed November 8, 2014
Not much to complain about in this property. Pool was supposed to be heated but was not working. It didn't bother me as I live in Florida but the people renting another cottage...
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$178
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1 / 32
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Dryer
  • Grill
  • Pool
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Part of the Nightly Group PALM GARDENS Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Stroll out your door and enjoy cafe con leche and the best Cuban Sandwiches at Sandy's Cafe, pulled pork... View all property information
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5 of 5 stars Reviewed February 12, 2014
We stay at the Palm Isle on White Street every year, and love it! It's perfectly close to everything in Old Town Key West, as well as the beaches. You can walk most places, but...
4 of 5 stars Reviewed January 2, 2014
Plenty of space for 2 people. Clean and well maintained. Bed was a little soft for me. It is on White St. and while not a busy street by city standards, it is one of the main...
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From
$5,000
Per Month
1 / 26
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (8) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Private Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The superb location at the top of Solares Hill, three blocks to the Historic Seaport and Duval Street, one block to the Public Library; Casa 625 will amaze you with the detailing, decorating and attention to... View all property information
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5 of 5 stars Reviewed December 23, 2013
The house is my perfect idea of what a Key West Conce Cottage should be. With Dade County pine walls, heated pool, all modern conveniences and perfect location for quite and easy...
5 of 5 stars Reviewed November 1, 2013
Really enjoyed the comfort of the unit. Close to everything but no need to leave!
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From
$275
Per Night
1 / 5
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the... View all property information
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3 of 5 stars Reviewed 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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From
$408
Per Night
1 / 29
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3 Bedrooms, 4 Bathrooms, Sleeps 8
Bookings
Details Reviews (49) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Heated Pool
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is within easy walking distance from Tropical Retreat to enjoy the exciting... View all property information
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5 of 5 stars Reviewed July 24, 2014
Everything was easy and perfect check in wise. Rooms were clean. Will stay here again. Walked to all bars and loved the tall ceilings.
5 of 5 stars Reviewed May 9, 2014
We rented the Tropical Retreat for our parents during our wedding in Key West. They were extremely happy with everything that this house had to offer. Some of the comments I heard...
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From
$368
Per Night
1 / 34
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Heated Pool
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom and... View all property information
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5 of 5 stars Reviewed March 10, 2013
2br 2 bath with sleeper sofa in main room. Pictures are accurate. Private pool and location make this an ideal stay for more than 3 nights. VERY close to the action on Duvall...
4 of 5 stars Reviewed October 8, 2011
DuPont House was a great place to stay in a great location. You are close enough to walk to everything but just far enough off on a side street so you don't hear any noise from...
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From
$358
Per Night
1 / 25
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Heated Pool
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
The beaches of the Atlantic Ocean are less than a 7 minute walk...4 blocks away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder,... View all property information
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5 of 5 stars Reviewed October 25, 2014
The townhouse is excellent. Location is also a huge positive. Clean and updated. Wifi was easy to access.
5 of 5 stars Reviewed August 5, 2014
This is a wonderful home in a great location - easy walking to almost everything. We loved the pool and the homes layout. Very clean and bright with TV's in both large bedrooms...
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From
$188
Per Night
1 / 31
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1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (28) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Andros Suite is a bi-level suite with a very spacious bedroom upstairs with a... View all property information
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5 of 5 stars Reviewed November 18, 2014
For the location, the price was a bargain. There were a couple of lights that needed to be replaced (no biggie). Andros suite was more of a condo. Full kitchen, and all the...
5 of 5 stars Reviewed November 12, 2014
We loved our stay at the Andros Suite. This is one of a gated cluster of duplex houses on the quieter side of Key West. The apartment was so nicely decorated and had everything...
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From
$300
Per Night
1 / 19
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Private Beach
  • Sauna
  • Shared Outdoor Pool...
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach ,... View all property information
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From
$198
Per Night
1 / 20
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1 Bedroom, 2 Bathrooms, Sleeps 4
Booking
Details Reviews (25) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! The bedroom is decorated in rich tropical colors. A writing desk and chair completes... View all property information
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5 of 5 stars Reviewed October 8, 2014
Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
5 of 5 stars Reviewed August 19, 2014
My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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From
$208
Per Night
1 / 28
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2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Sea Breeze features all the amenities of home...and then some! A full kitchen with glass top stove, dishwasher, icemaker, blender, toaster, coffee maker and radio/CD player to play your favorite Jimmy Buffet CD while enjoying a fresh cup of brew...there isn't a better way to start your day in... View all property information
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3 of 5 stars Reviewed September 30, 2014
If you don't mind the Anchors away people hanging out around your bedroom porch all hours of the night, or the people up stairs playing basketball at 430 in the morning, you...
2 of 5 stars Reviewed September 19, 2014
The rental office is well organized and accommodating, and that is the only good thing I can say. The unit itself was clean, though sparsely furnished, especially the bathroom...
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From
$268
Per Night
1 / 28
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit with Mexican Tile downstairs and... View all property information
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2 of 5 stars Reviewed August 12, 2014
Overall the unit was nice. A few rips in the living room chair; could use recovering. The kitchen had all the amenities and we lacked for nothing. The master bedroom was very...
5 of 5 stars Reviewed August 6, 2014
Excellently furnished, Immaculately clean. Completely up to date appliances and amenities. (Washer & dryer just off the kitchen!) Tip-Bring your own laundry detergent Traveled...
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From
$7,000
Per Month
1 / 11
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Located at 516 Elizabeth Street, the Pinder House is an address and house of distinction! Previously owned by Theopolis Pinder of the historic Pinder Family, whose roots go back to the 1850’s, this historic... View all property information
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4 of 5 stars Reviewed January 23, 2014
B+ no Choices in cable channels no prkg On site , parrot sanctuary adjacent Property's remote pool. Access. K
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From
$2,650
Per Week
1 / 12
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2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Housekeeping...
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
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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From
$138
Per Night
1 / 22
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Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
The Truman Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
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3 of 5 stars Reviewed October 29, 2014
Late reservation so I couldn't be picky. Bed mattress needs to be replaced. Nighttime security light didn't work. Pool nice. Clean full kitchen
5 of 5 stars Reviewed June 6, 2014
The home was clean and quiet. It was just perfect for the two of us. We would recommend it to others.
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From
$338
Per Night
1 / 29
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
One block from Center St, Hemingway's View is a 3 bedroom, 2 bath charming turn-of-the-century Conch cottage. Each of the 3 bedrooms are air-conditioned. Both bathrooms have marble floors, large closets, hairdryers, and tubs with showers. The rear bath has a marble topped vanity with double sinks... View all property information
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4 of 5 stars Reviewed June 30, 2014
Great house pretty much right off Duval. Very close to great restaurants, bars, and shops, and a very short walk to the beach. Plenty of room for three couples and one child. Not...
5 of 5 stars Reviewed April 23, 2014
From the moment we received our key to the time we turned it in to go home. Everyone involved made our stay perfect.
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From
$258
Per Night
1 / 29
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2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
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Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
One half of the group unit Tradewinds Opposite Windward Isle , the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and walls,... View all property information
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4 of 5 stars Reviewed June 5, 2014
This house is the perfect little hideaway. Close enough to Duval and all the action but far enough away that you can shut out the world and just relax. The hot tub is very...
5 of 5 stars Reviewed March 27, 2014
Leeward Isle is a great place to stay for a trip to Key West. It is within walking distance to all the hot spots and to the beautiful sunsets at Mallory Square, yet far enough...
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From
$158
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1 / 27
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Formerly Amelia St Hideaway With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-styled complex, this 1 bedroom/1 bathroom condominium features a full... View all property information
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3 of 5 stars Reviewed October 5, 2014
At the south end of Duval St 4 blocks from southern most end of US. Next door to Key West Pub, great music and Amy the bartender is super great. Across the street is Latte another...
4 of 5 stars Reviewed March 20, 2014
The accommodations were nice and close to everything. We especially liked the balcony.
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$288
Per Night
1 / 10
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Grill
  • Housekeeping...
  • 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
$188
Per Night
1 / 30
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1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
AUDUBON'S LIVING ROOM HAS JUST BEEN REFURBISHED WITH NEW FURNITURE INCLUDING NEW CHAIRS AND A NEW QUEEN SLEEPER SOFA! The Audubon House is an historic free-standing one bedroom cottage featuring all the comforts of home, and more! The spacious, beautifully furnished great room features a living... View all property information
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4 of 5 stars Reviewed November 20, 2014
We booked here for one night because of the location. This worked out well for 2 couples - one private bedroom with full bath and separate entrance, one pull-out sofa bed with a...
4 of 5 stars Reviewed January 7, 2014
The listing was completely accurate and the property maintenance was good. The furniture and utensils (knives, peeler, grater) were tired and due for replacement. We had very...
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From
$408
Per Night
1 / 28
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Private Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located on one of old town's prettiest historic streets, Frances Street. Casa Serendipity is one of the finest examples of the 'conch cottage' style architecture that Key West is famous for. Designed to accommodate a family, this three-bedroom home has two full baths, one full bath upstairs and one... View all property information
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4 of 5 stars Reviewed November 11, 2014
The house was great. Roofs are a little low upstairs but still good enough. Nice patio area and a pool in the backyard. Only a few minutes walking distance from Duval St.
2 of 5 stars Reviewed October 27, 2014
My friends and myself stayed at this house during the week of Fantasy Fest in October of 2014. The house was nice, but was too far from town to walk everyday. Next time we will...
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From
$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
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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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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...
4 of 5 stars Reviewed May 5, 2014
Great location - walking distance to everything! It was clean and friendly great for the price! Would rent Monroe Efficiency again
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$208
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1 / 22
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Overlooking the gardens and lily pond, the entrance to this spacious unit is through a totally enclosed private decked courtyard with a 4-person spa, table and chairs. Inside this spacious unit you will find a living room with cathedral ceilings, 56” TV, A/C, stereo, queen sleeper sofa and fabulous... View all property information
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5 of 5 stars Reviewed November 4, 2014
My wife and I stayed at the Sunset Suite - Nightly which is managed by Key West Vacation Rentals. This was our first trip to Key West as we went for the Meeting of the Minds. We...
3 of 5 stars Reviewed March 29, 2014
First the pros. The location is great if you want to be close to Duval Street and an easy walk to many restaurants and other attractions. The pool area is very nice and well...
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • 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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