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Holiday Rentals in Key West, FL

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    €240
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    1 / 14
    4 of 5 stars (12) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    €92
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    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
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    €322
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    1 / 18
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    €207
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    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
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    • 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 15 April 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 10 February 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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    €137
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    1 / 20
    5 of 5 stars (10) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • ?
    About this property
    The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment with a king size bed in the bedroom and a queen size sleeper sofa in the living area. It accommodates 2-4 people. This property is rented by the week from Saturday to Saturday, it is not a hotel; it is a privately... View all property information
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    5 of 5 stars Reviewed 14 October 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 11 August 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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    €323
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    1 / 19
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Sauna
    • Shared Outdoor Pool...
    • Waterfront
    • 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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    €249
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    1 / 15
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
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    5 of 5 stars Reviewed 19 March 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
    5 of 5 stars Reviewed 3 March 2015
    My wife and I stayed in Shelley's Rooftop Hideaway for the entire month of February. It was fantastic, and we had a great time in Key West, due in no small part to the location...
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    €193
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    1 / 17
    5 of 5 stars (13) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
    Overview Reviews (13) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • 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 17 March 2015
    Stayed in the Bimini Suite with 2 friends . My wife made the reservations and dealt directly with Evelyn and David who were always reachable and friendly . You will not regret...
    4 of 5 stars Reviewed 13 March 2015
    We stayed in the Bimini Suite for two nights in early March. It was perfect size for us - two retired couples. The owner happened to be there working on the roof and was very...
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    €129
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    1 / 13
    1 Bedroom / 1 Bathroom / Sleeps 4
    traveller have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • 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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    €161
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    1 / 10
    4.5 of 5 stars (7) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Gym
    • 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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    5 of 5 stars Reviewed 5 March 2015
    Located in a private condo complex, the unit we stayed in featured excellent amenities while also clean and well maintained. Location to old town and Duval will require...
    5 of 5 stars Reviewed 11 December 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...
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    €184
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    1 / 27
    5 of 5 stars (35) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (35) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Hot Tub
    • 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 8 January 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 31 December 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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    €183
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    1 / 14
    5 of 5 stars (15) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers 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
    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 2 February 2015
    We stayed here for a week, for our destination wedding. We were able to entertain all of our wedding guests from out of town. Perfect size for our needs; great front porch...
    5 of 5 stars Reviewed 18 November 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...
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    €182
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    1 / 10
    5 of 5 stars (3) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    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 12 July 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 12 June 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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    €174
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    1 / 13
    4 of 5 stars (6) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    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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    3 of 5 stars Reviewed 11 February 2015
    Clean, noisy window air conditioner, ants. Close to water. Staff pleasant and efficient. Musty smell but comfortable bed.
    4 of 5 stars Reviewed 10 July 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...
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    €2,765
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    1 / 34
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    28 NIGHT MINIMUM STAY REQUIREMENT - ANGELFISH COTTAGE 2 Bedroom 1 Bath Historic Conch House on a quiet Lane in Historic Old Town Key West This monthly vacation home is located in the heart of Historic Old Town Key West Florida on a very private, quiet lane. Restaurants and bars, marinas and... View all property information
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    €263
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    1 / 11
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Hot Tub
    • 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 22 March 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 23 January 2014
    The condo was fantastic. I was clean convenient and would recommend to anyone. This was exactly as described.
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    €189
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    1 / 14
    5 of 5 stars (44) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Gym
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The... View all property information
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    5 of 5 stars Reviewed 24 February 2015
    This trip to Key West was partially a college graduation present for our son and a family vacation. We had the most wonderful week and this was partially due to our stay at...
    5 of 5 stars Reviewed 1 February 2015
    All four of us were very happy with our stay ... very clean, beautiful, safe, conveinient location. Inside of the condo is as pictured and we couldn't have been more pleased with...
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    €277
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    1 / 26
    5 of 5 stars (28) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Sauna
    • 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 25 March 2015
    The condo is very spacious, lots of room for everyone and in a great location. The owners left us some very helpful tips and ideas for what to do in Key West. The Condo was clean...
    5 of 5 stars Reviewed 16 March 2015
    This Condo was perfect for my friends and I. It had all the comfort of home right down to small details. Everything in the kitchen you could need. The pool area is beautiful...
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    €267
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    1 / 26
    5 of 5 stars (14) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers 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 April 4-6 (2 nights) and pay a reduced rate of $765 for both nights instead of $1,025. -- Note, taxes and fees will be added to all rates.... View all property information
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    5 of 5 stars Reviewed 7 December 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 2 November 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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    €4,148
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    1 / 43
    4 of 5 stars (1) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    28 NIGHT MINIMUM STAY REQUIREMENT - SEABREEZE 4 Bedroom 3 Bath with Off Street Parking, Private Heated Pool, Fitness Center, Gorgeous!! A warm color scheme and meticulous design details lend an elegant tropical ambience to this spacious four bedroom, 3 bath home located in the 'Sanctuary' on the... View all property information
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    4 of 5 stars Reviewed 1 May 2014
    We rented Seabreeze for a month! It was in the Golf Course a gated community. It was a great home away from home. Very comfortable, stocked well. Had a few glitches with the...
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    €275
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    1 / 9
    4.5 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (14) Make Enquiry
    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 28 October 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 11 September 2014
    Great location for walking and biking all around Key West. Close to restaurants and attractions. Limited Parking.
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    €194
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    1 / 5
    3 of 5 stars (1) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the... View all property information
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    3 of 5 stars Reviewed 3 September 2013
    Our first night I was kept up until 4 AM by noisy you people and I love to hang and have fun but come on they were really poorly behaved. The following night Saturday of Labor Day...
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    €548
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    1 / 18
    3.5 of 5 stars (10) Average
    4 Bedrooms / 4 Bathrooms / Sleeps 12
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    • 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 8 January 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 3 January 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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    €3,761
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    1 / 35
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • 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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    4.5 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
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    • Satellite TV
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • 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 for... View all property information
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    5 of 5 stars Reviewed 20 May 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 21 August 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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    1 / 10
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
    • ?
    • x
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    • 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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    2 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
    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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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    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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    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Suitable for children
    • x
    • x
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    About this property
    Incredible resort during the 'peakest' of peak seasons in Key West, Florida. This extraordinary resort is not right in the heart of the Duval Street area, and it therefore offers the best of both worlds to visitors. Since it's within a short car or cab or scooter or bike ride from the Old Town... View all property information
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    1 / 37
    4 of 5 stars (1) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
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    • Satellite TV
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    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
    • x
    About this property
    This 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 / 7
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • 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 / 11
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Suitable for children
    • ?
    • x
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    • ?
    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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    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Dryer
    • Hot Tub
    • Ocean Views
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • 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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    1 / 9
    5 of 5 stars (8) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (8) Make Enquiry
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
    About this property
    Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50', 42', and 27' flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home... View all property information
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    5 of 5 stars Reviewed 9 March 2015
    We loved our stay at Catherine St. The home is set up with everything that you could ever need. The pool is very private. Skinny Dipping a definite. All of the furniture is custom...
    5 of 5 stars Reviewed 26 February 2015
    My husband and I spent both January and February here and loved it. Great beds, lots of room as we had at least another couple stay with us and twice we have three couples. Pool...
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    1 / 14
    4.5 of 5 stars (16) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (16) Make Enquiry
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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
    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 19 August 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 28 October 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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    1 / 19
    5 of 5 stars (9) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (9) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • 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 4 September 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 25 August 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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    4.5 of 5 stars (5) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Sauna
    • Shared Outdoor Pool...
    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 2 January 2015
    We loved our stay in Key West which was enhanced by the condo's location, views, lovely large heated pool and jacuzzi with views of Atlantic Ocean, our balcony with view of ocean...
    5 of 5 stars Reviewed 30 May 2014
    The vacation property is well worth the price. It's well maintain with beautiful views and perfect pool. Very spacious and quiet, perfect for a family. The condo is a 2 to 3...
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    1 / 19
    5 of 5 stars (8) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (8) Make Enquiry
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    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Truman Annex Best Location in Town!! 2 Bedroom 1 Bath ground floor Shipyard Condo. This beautiful townhome sits on a private quiet walking lane and is just a 5 minute walk to downtown where you will find Key West's famous bars and shopping. Also a 10 minute walk to Ft. Zachary Taylor, our... View all property information
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    5 of 5 stars Reviewed 23 January 2015
    While the Artist Cottage was not available, the owner had another Shipyard condo that was perfect for us. The property is nicely maintained, the pool clean and warm, and the...
    5 of 5 stars Reviewed 29 June 2014
    Wonderful location was able to walk to experience Key West. Something for everyone to enjoy with 2 older teenagers. Did something every day but was very relaxing, never felt...
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    1 / 7
    5 of 5 stars (25) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (25) Make Enquiry
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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 23 July 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 12 March 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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    1 / 13
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
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    • Elder access
    • x
    About this property
    This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer. Quaint and charming, with a view of the... View all property information
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    1 / 23
    4 of 5 stars (2) Very good
    6 Bedrooms / 6 Bathrooms / Sleeps 16
    Overview Reviews (2) Make Enquiry
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    • Air Conditioning
    • Dishwasher
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    • Grill
    • Internet Access
    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West's Old Town. It's like having your own private hotel. If you are vacationing with family and friends, Top of Duval offers a truly unique layout with six individual... View all property information
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    3 of 5 stars Reviewed 2 March 2015
    We traveled with a group of six couples and each had their own suite. The rooms were very clean and decorated in lively colors and an island motif. The problem with the Club...
    5 of 5 stars Reviewed 23 December 2014
    This place was fantastic. With friends or family every room has its own bathroom and kitchen so you Can spread out. The front of building is right in the action on duval and the...
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    1 / 5
    5 of 5 stars (3) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • 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
    Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our home across the pond. We know you will enjoy your time in Key West as much as we do and Our... View all property information
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    5 of 5 stars Reviewed 18 January 2015
    Loved our stay in this very homely apartment. The location was excellent in the private Truman annex but close to Duval st and the local Green Parrot! The apartment was very well...
    5 of 5 stars Reviewed 11 October 2010
    This was our first time visiting Key West and we truly enjoyed our stay at this condo. It was clean, well maintained and had all of comforts and amenties of home. The location...
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    1 / 14
    5 of 5 stars (8) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (8) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Private Outdoor...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    THIS PROPERTY IS A MONTHLY ONLY RENTAL 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... View all property information
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    4 of 5 stars Reviewed 23 April 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 2 July 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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    4.5 of 5 stars (31) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (31) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Gym
    • Internet Access
    • Sauna
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Fully Appointed Suite- Condominium Unit- 2 Bedrooms, 2.5 Baths (Sleeps 4-5) Our beautifully landscaped property and contemporary housing will provide you with a serene tropical setting ideal for a relaxing vacation getaway. Located off the azure waters of the Atlantic Ocean, minutes away from... View all property information
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    5 of 5 stars Reviewed 26 March 2015
    Great value for money. I am not a hot tub fan so this was not important to me. The weather did not cooperate but this did not matter as we were having such a great time.
    5 of 5 stars Reviewed 25 March 2015
    Condo was beautiful inside and out. The pool and grounds were amazing. The condo itself was clean and comfortable. Wanted to take the bed home with us, it was so comfortable...
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    1 / 11
    3 of 5 stars (4) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Enquiry
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Fabulous spacious two bedroom condominiums, directly on the Atlantic Ocean in Key West Florida. The Condo is fully equipped with a full size Kitchen. There is also a full size washer & dryer for your convenience. All rooms have a color cable TV and the unit has high There is an extensive... View all property information
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    4 of 5 stars Reviewed 11 March 2015
    We stay 4 days at 1800 Atlantic. Place is well located and secure. The rental company is very accommodating and friendly. The place is at the end of the beach and just a short...
    2 of 5 stars Reviewed 22 August 2014
    The condominium which appears to be clean is not clean at all. Dust everywhere when you get close. There are ant traps in every corner of the kitchen and there were ants...
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    1 / 17
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Enquiry
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    • 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 22 May 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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    4.5 of 5 stars (39) Very good
    10 Bedrooms / 6 Bathrooms / Sleeps 20
    Overview Reviews (39) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    THIS ISN'T JUST A HOUSE, THIS IS YOUR OWN PRIVATE MINI RESORT IN KEY WEST, FLORIDA. THIS IS THE PROPERTY USED BY MTV TO FILM THE 2006 REAL WORLD KEY WEST. 500 FEET OF OCEANFRONT, 8 to 10 BEDROOMS are available (sleeps up to 20) , 5 1/2 baths, 11 plasma TVs, pool table (and Ping Pong), tennis... View all property information
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    5 of 5 stars Reviewed 26 March 2015
    This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in...
    4 of 5 stars Reviewed 5 February 2015
    Our group of 18 stayed at the MTV house for my 60th birthday. We had a ball! The owner(Andrew) was very accommodating to our needs. The house was big enough for all of us to be...
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    4.5 of 5 stars (19) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (19) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    CALL AND ASK ABOUT OUR WEEKLY SPECIAL WITH 1 NIGHT FREE! You will love staying in this great Key West historic old town location where 90% of the residents are local. They each have an interesting Key West tale to tell and are a very warm,friendly and diverse group. Here you will absorb the... View all property information
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    3 of 5 stars Reviewed 4 March 2015
    We will go to a hotel in the future. The apartment was cute but when we arrived one of the a/c units didn't work, the porch light didn't work, the light on the ceiling fan in the...
    4 of 5 stars Reviewed 22 November 2014
    2nd time this year going to Key West & staying at this location. Perfect location. quiet, side street, around corner from grocery store & Sandy's Cafe, best coffee ever! Less than...
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    1 / 15
    4.5 of 5 stars (10) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (10) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Make our lovely home your dream vacation destination in fun-filled tropical Key West, Florida. '1800 Atlantic' is Key West's premiere luxury condo complex on a private Atlantic Ocean beach. Our beautifully furnished large 2 bedroom and 2 bath condo overlooks a serene tropical garden. Both... View all property information
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    5 of 5 stars Reviewed 16 March 2015
    Patrick was excellent. He responded to emails quickly. There were no extra charges. The location was just as described in a secure building. The condominium was very clean...
    5 of 5 stars Reviewed 16 February 2015
    We had a wonderful week at 1800 Atlantic. Patrick was a pleasure to deal with and was responsive to all our questions. The unit was in excellent condition. I was not prepared...
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    1 / 34
    Studio / 1 Bathroom / Sleeps 2
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    Amenities & Details
    • Air Conditioning
    • Dryer
    • Internet Access
    • Ocean Views
    • Satellite TV
    • Washer
    • Waterfront
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
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    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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