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Rentals with Pool in Key West, FL

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    $240
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    4 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    5 of 5 stars (15) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    5 of 5 stars (31) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    5 of 5 stars (18) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Wi-Fi
    • Watersports Nearby
    • TV
    • Air Conditioning
    • Dryer
    • Grill
    • Refrigerator
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • 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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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 2, 2015
    We stayed for three nights in April. Checked in Saturday, and as we were unloading our car owner came by to say hi and ask if we had any questions. She answered the few...
    5 of 5 stars Reviewed April 5, 2015
    Great old house with lots of character in the perfect location. Very clean, comfortable beds, and a great pool area. Had one minor issue that management fixed for us right away...
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    $295
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    1 / 26
    5 of 5 stars (16) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Water Views
    • Wi-Fi
    • TV
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
    About this property
    ******************************************************************************** TAKE 20% OFF: -- Stay September 3-6 (3 nights) and pay a reduced rate of $850 for all three nights instead of $1,065. -- Note, taxes and fees will be added to all rates.... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 23, 2015
    My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view...
    5 of 5 stars Reviewed June 16, 2015
    My husband and I stayed at this condo for 2 weeks. Had the best vacation ever. The view from the balcony is fabulous and tranquil. Didn't want to leave. The condo itself is...
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    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • DVD Player
    • Ocean Views
    • Satellite TV
    • Shared Tennis Court
    • Washer
    • Deck
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table and... View all property information
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    Key West, Florida Keys 33040
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    $185
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    1 / 5
    3.5 of 5 stars (2) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    • Shared Tennis Court
    • Grill
    • Air Conditioning
    • Internet Access
    • Garage
    • Satellite TV
    • Patio
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    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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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 25, 2015
    This room had all the comforts of home. A bit dated, but very clean. A bit of a drive to Duvall though. About a 10-12 min cab ride. We were there with 6 people and the cab drivers...
    3 of 5 stars Reviewed September 3, 2013
    Our first night I was kept up until 4 AM by noisy you people and I love to hang and have fun but come on they were really poorly behaved. The following night Saturday of Labor Day...
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    1 Bedroom / 2 Bathrooms / Sleeps 4
    travelers have booked this property
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    • Air Conditioning
    • Internet Access
    • Deck
    • Ocean Views
    • Water Views
    • Staffed Property
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a 'closet... View all property information
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    Key West, Florida Keys 33040
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    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Washer
    • TV
    • Deck
    • Hot Tub
    • Sauna
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    We are situated in New Town on the paradise island of Key West, about 12 minutes drive from downtown Duval Street. This romantic studio cottage consists of a bedroom with very comfortable king sized bed and a bathroom, with a pool and lush landscaping right outside your door. It has air... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
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    • Refrigerator
    • Stove
    • Internet Access
    • Balcony
    • Linens Provided
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveler have booked this property
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Deck
    • Watersports Nearby
    • Elevator/Lift access
    • Air Conditioning
    • Shared Tennis Court
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights*** MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 17, 2015
    Stayed here for 2 months while I was having my house remodeled and I was very pleased with the facilities and the unit. The condo has been nicely redone and very well stocked...
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    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travelers have booked this property
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    Amenities & Details
    • Stereo System
    • Air Conditioning
    • DVD Player
    • Dryer
    • Washer
    • Garage
    • Refrigerator
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 18, 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 March 2, 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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    4 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • There Are Tennis...
    • Internet Access
    • Hot Tub
    • Washer
    • DVD Player
    • Satellite TV
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 28, 2015
    Traveled with husband and teenage son. Plenty of room. Away from the really busy area of Key West. Clean. Close to the beach (brisk walk or bike ride). Did not use the pool...
    4 of 5 stars Reviewed March 30, 2015
    I traveled with my wife and 3 teen daughters for spring break. The condo was very nice with plenty of room for my family. The owner responded quickly to my Tripadvisor request and...
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    $1,700
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    1 / 26
    5 of 5 stars (24) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Stereo System
    • Washer
    • Internet Access
    • Satellite TV
    • Deck
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 16, 2015
    Spotlessly clean place. Everything as advertised. Quiet neighborhood in a semi-gated community. We took the auto-train to Sanford and drove down to Key West. Many quality...
    5 of 5 stars Reviewed May 5, 2015
    We scheduled our vacation with Jim and Joanne at Casa Del Sol and experienced a no hassle application. Our friendly hosts gave us all the information we needed to enjoy ourselves...
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    $10,750
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    1 / 24
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Housekeeping...
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    AVAILABLE FOR STAYS OF 28 DAYS OR LONGER. Vacation in style in this 2 bedroom, 2 bathroom beautifully furnished Keys Home, with lush landscaping with over 20 palm trees, tiki hut/bar with bar stools, heated swimming pool, pool deck chairs, private sandy beach, outdoor deck with dining, outdoor... View all property information
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    Key West, Florida Keys 33040
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    $210
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    1 / 27
    5 of 5 stars (42) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (42) Make Inquiry
    Amenities & Details
    • Hot Tub
    • Stereo System
    • Wi-Fi
    • Satellite TV
    • Watersports Nearby
    • Air Conditioning
    • Staffed Property
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • 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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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 13, 2015
    Pam your condo was great and easy access to all the great amenities of Key West. I loved the pool and the conveniences of home. We were located near the beach, we rented bicycles...
    5 of 5 stars Reviewed June 17, 2015
    It is away from the loud touristy area, which is what I wanted. We saved a ton of ,only by cooking our own meals. Condo was nice and clean. Beds were pretty comfortable. Pool...
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    $225
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    Amenities & Details
    • Wi-Fi
    • Hot Tub
    • Washer
    • Elevator/Lift access
    • Watersports Nearby
    • There Are Tennis...
    • Air Conditioning
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach. This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony... View all property information
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    Key West, Florida Keys 33040
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    $150
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    1 / 30
    4.5 of 5 stars (57) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (57) Make Inquiry
    Amenities & Details
    • Washer
    • Satellite TV
    • Stereo System
    • Wi-Fi
    • DVD Player
    • Watersports Nearby
    • Deck
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    All new luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in NEW gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa in LR. We are 4 miles from Duval St. and 2... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 4, 2015
    Judy's condo, Tee by the Sea is really a great place to stay. The location is away from the crowds but close enough to be only a short drive or bike ride away. The condo has...
    5 of 5 stars Reviewed March 3, 2015
    We loved our vacation! The house was in a great location, easily accessible to many of the best rated restaurants and local convenient stores. We LOVED the provided bikes and rode...
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    $175
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    5 of 5 stars (8) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Water Views
    • Deck
    • Air Conditioning
    • Watersports Nearby
    • Stereo System
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    What a unique way to spend time on the water. Its not a 5 star hotel but you will have a nice clean private chartered boat on the water. Get ready for a unique vacation that others will envy. Boat is a 2003 Beneteau 331, while the boat is dockside the marina has electricity, water and Internet.... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 18, 2015
    After a bit of a problem confirming the reservation, and no help from Trip Advisor, we arrived as scheduled on 5-15 and were met by Yanna who gave us a detailed tour of the boat...
    5 of 5 stars Reviewed March 6, 2015
    We spent 3 nights on this boat. James the owner was easy going and welcoming. He explained all we needed to know and was available by phone for any questions or concerns. Boat...
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    $375
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    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Water Park Nearby
    • Waterfront
    • There Are Tennis...
    • Water Views
    • Ocean Views
    • Washer
    • Deck
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Look at this! July 4th weekend is open for your holiday stay! Obsession 37'ft. 1979 O'Day completely renovated with new interior and new varnish and paint throughout. $375/night for two people three nights preferred minimum. Half day 4 hour sail worth $600 included free (please plan cash 20% tip... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $350
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    1 / 22
    2 of 5 stars (1) Poor
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    Amenities & Details
    • Waterfront
    • Refrigerator
    • Air Conditioning
    • Grill
    • Internet Access
    • Sauna
    • Gym
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Key West, Florida Keys 33040
    2 of 5 stars Reviewed May 18, 2015
    Would be lovely with lots of maintenance and repairs. Water leak in the cabin, smells humidity, surage, fridges are sticky from dirt and the fridge door won’t even close. Towels...
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
    traveler have booked this property
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    • Private Outdoor...
    • Air Conditioning
    • Deck
    • Internet Access
    • Washer
    • Dryer
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    ******** Key West laws state that this property can only be rented out monthly******* This lovely home is in the Casa Marina District of Key West. It has a front porch, front balcony that the 2 smaller bedrooms have access to, a large patio by the heated private pool in the back yard, and a... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $183
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Dryer
    • DVD Player
    • Satellite TV
    • Private Outdoor...
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Key West, Florida Keys 33040
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    $300
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    1 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Watersports Nearby
    • Waterfront
    • Shared Tennis Court
    • Housekeeping...
    • Staffed Property
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    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 amenities... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 1, 2015
    My brother, mother and I and our spouses met up in Key West for a great vacation. This condo had plenty of space inside and out for 6 adults and was very comfortable. The deck...
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    $1,250
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    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Shared Tennis Court
    • Stereo System
    • Water Park Nearby
    • Deck
    • Air Conditioning
    • DVD Player
    • TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Elegantly furnished Key West vacation condo in the historic Truman Annex in the heart of Old Town in Key West. This is the premier gated community in Key West, bordering the Atlantic Ocean. Grounds of the Annex are beautifully landscaped. The Shipyard units are done in the traditional Key West... View all property information
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    Key West, Florida Keys 33040
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    1 / 24
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Washer
    • DVD Player
    • Stereo System
    • Internet Access
    • Private Outdoor...
    • Deck
    • Satellite TV
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
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    About this property
    2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered... View all property information
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    Key West, Florida Keys 33040
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    1 / 18
    5 of 5 stars (5) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
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    • Watersports Nearby
    • Water Views
    • DVD Player
    • Wi-Fi
    • TV
    • Air Conditioning
    • Ocean Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
    About this property
    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 3 WEEKS please contact us for reduced rates! Fully equipped from bow to stern -- Galley (kitchen to the non-boat speakers) has all cooking, baking and grilling items; 3/4 fridge/freezer, Keurig... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 26, 2015
    We had two couples staying for a long weekend,we couldn't of asked for a better place to stay,we have stayed in key west over 50 times in the past 10 years at numerous places and...
    5 of 5 stars Reviewed May 25, 2015
    It was a fun and unique vacation! At first it took some getting used to, flushing the toilets, water supply, close quarters, etc. But by the end that's what made it memorable. The...
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    • Ocean Views
    • Hot Tub
    • Wi-Fi
    • Sauna
    • Air Conditioning
    • Shared Tennis Court
    • Satellite TV
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
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    Key West, Florida Keys 33040
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    1 / 11
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    • Hot Tub
    • Air Conditioning
    • Private Outdoor...
    • Elevator/Lift access
    • Gym
    • Private Tennis Court
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Elder access
    • ?
    About this property
    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 26, 2015
    Very lovely condo!!! Close to everything you need! It was our first time to key west and when we return we will definitely try to stay here again!!!! We really enjoyed our time.
    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...
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    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Shared Outdoor Pool...
    • Internet Access
    • Satellite TV
    • Linens Provided
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • x
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    About this property
    Room 6 is conveniently located on the main floor. It has a door that opens onto the side deck with a secluded sitting area. The front porch sitting area is only a few steps away. People that stay in Room six often comment on how pleasant it is to wake up to the smell of breakfast cooking nearby in... View all property information
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    Key West, Florida Keys 33040
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    $175
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    1 / 7
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travelers have booked this property
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    • Satellite TV
    • Washer
    • Elevator/Lift access
    • Internet Access
    • Dryer
    • Air Conditioning
    • Gym
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
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    About this property
    Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool on property, perfect for sunbathing. Jacuzzi and gym. Tennis court. Small boats on trailer allowed.... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 13, 2015
    My family and I traveled to Key West for the sunset wedding of my Grandson and Bride. What a wonderful stay we had over 5 days! The condo had everything except groceries and we...
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    4.5 of 5 stars (8) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travelers have booked this property
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    • Shared Tennis Court
    • Gym
    • Internet Access
    • Air Conditioning
    • Dryer
    • Washer
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • 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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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 25, 2015
    The people who work on property were very friendly. The main areas in the condo were very clean. The guest bath could have been cleaner. The kitchen had everything you would need...
    5 of 5 stars Reviewed March 5, 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...
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    3 Bedrooms / 4 Bathrooms / Sleeps 8
    traveler have booked this property
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    • Ocean Views
    • Shared Tennis Court
    • Pool Table
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    28 DAY MINIMUM STAY IS MANDATED BY COUNTY LAW. PLEASE DO NOT SEND ENQUIRIES FOR SHORTER PERIODS!! Charted back in the 1800's, Shark Key was named by early explorers for its shark-like shape. This exclusive island boasts more than 2 miles of pristine shoreline, lush foliage, and a sparkling lagoon... View all property information
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    Key West, Florida Keys 33040
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    $205
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    5 of 5 stars (46) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    • Air Conditioning
    • Hot Tub
    • Shared Tennis Court
    • Stereo System
    • Private Outdoor...
    • DVD Player
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • 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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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 14, 2015
    From the beginning to the end, the process of renting the condo was made very easy owners were a pleasure to deal with and the condo was nice, clean and comfortable and all...
    5 of 5 stars Reviewed June 11, 2015
    Grandparents, Children,Grandchildren, we all had a great stay. Our experience ranged from charter boat fishing to trips to the beach.
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    $138
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    1 / 10
    Studio / 1 Bathroom / Sleeps 2
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    • Shared Outdoor Pool...
    • Parking
    • Air Conditioning
    • Linens Provided
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    It is a pleasure to present the recently renovated Room Nine! It used to be a good room, now it's a great room! Comfortable and very peaceful, this room was originally opened up to make use of a portion of the attic space. Note that the ceiling is sloped in two directions and some taller guests... View all property information
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    Key West, Florida Keys 33040
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    $5,000
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    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
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    • Air Conditioning
    • TV
    • Stereo System
    • DVD Player
    • Wi-Fi
    • Private Outdoor...
    • Watersports Nearby
    • There Are Tennis...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 8, 2014
    This is a wonderful conch house in Old Town, Key West. The house is just around the middle of Old Town, so you can walk or bike to the harbor, the ocean, and the great music at...
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    1 / 17
    2 Bedrooms / 5 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Satellite TV
    • Water Views
    • Wi-Fi
    • Hot Tub
    • Watersports Nearby
    • Ocean Views
    • Staffed Property
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    This property is located on the north side of Key West 4 miles from downtown.It is available from Dec. 27th to January 3rd. A great venue for the holiday season. This is a great two bedroom two bath unit with master bedroom and en suite. Private balcony which overlooks outdoor infinity pool. Also a... View all property information
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    Key West, Florida Keys 33040
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    $6,950
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    1 / 18
    3 Bedrooms / 5 Bathrooms / Sleeps 9
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    • Wi-Fi
    • Air Conditioning
    • Children's Pool
    • Waterfront
    • Game Room
    • Hot Tub
    • Watersports Nearby
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
    About this property
    One of the very few & one of the largest Ocean Front Suites in Key West This place is really incredible! it's one of the largest ocean front suites in Key West. 3 bed room, 2 bath, 2200 square ft .You are literally 20 yards from the oceans edge. The wrap around balcony affords 90' of unobstructed... View all property information
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    Key West, Florida Keys 33040
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    1 / 8
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Wi-Fi
    • Refrigerator
    • Air Conditioning
    • Hot Tub
    • TV
    • Dryer
    • Stove
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
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    • Elder access
    • x
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    About this property
    KEY WEST VACATION CONDO RENTAL DESCRIPTION Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor. It is approximately 1200 sq ft... View all property information
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    Key West, Florida Keys 33040
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    $178
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    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool...
    • Linens Provided
    • Parking
    • Satellite TV
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    • Pet-friendly
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    • Child-friendly
    • x
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    • x
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    About this property
    Room 5 is on the ground floor with a King-sized bed, private bathroom & has access to a wraparound porch. The Curry House is an historic piece of Old Key West. Pearl Curry originally opened her home as 'Curry's Rooms' in the mid-1900's. Now the inn offers nine beautiful guestrooms and the... View all property information
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    Key West, Florida Keys 33040
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    $3,500
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    2 Bedrooms / 4 Bathrooms / Sleeps 6
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    • Wi-Fi
    • Private Outdoor...
    • Balcony
    • Grill
    • Terrace
    • Linens Provided
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    A hidden jewel in the old town of Key West. A private garden, with pool, and fountain, covered porch, and space to sun. Comfortable bedrooms, with a loft to sleep 2. fully equipped kitchen, air-conditioning internet, tv, cable. Bes quiet neighborhood. This home rents by the month and is occupied a... View all property information
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    Key West, Florida Keys 33040
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    $931
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    2 Bedrooms / 5 Bathrooms / Sleeps 4
    traveler have booked this property
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    • Dryer
    • Watersports Nearby
    • Private Outdoor...
    • Wi-Fi
    • Washer
    • TV
    • There Are Tennis...
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    MONTHLY RENTAL ONLY Buoy's Backyard - an authentic Key West retreat in the historic district just a block from upper Duval (the quiet end), two blocks from Hemingway House, and three blocks to Southernmost Buoy and Beach. Brick driveway provides private gated parking for two cars. This home has... View all property information
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    Key West, Florida Keys 33040
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    $188
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    1 / 28
    4.5 of 5 stars (22) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    traveler have booked this property
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    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Patio
    • DVD Player
    • Internet Access
    • Deck
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • x
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    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... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 30, 2015
    As good as the unit was and it really was its the people behind the organisation that make the difference ! I had stuffed up my original booking by 4 weeks, hey I'm old, it's...
    5 of 5 stars Reviewed December 23, 2014
    Trying to pick out a vacation rental in Key West is like finding a needle in a haystack. You just never know what you are going to get. I did a lot of research before we settled...
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    5 of 5 stars (4) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Private Outdoor...
    • Stereo System
    • Deck
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
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    About this property
    Chick-A-Pea’s Cottage: Located in the gallery district of Key West. The house is steps off of Duval St. near Hemmingway’s house, the Southernmost Point, the Butterfly Museum and great shops, restaurants and bars . The location is quiet & private… yet in the heart of key west The house is a... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 12, 2014
    My family and fiance stayed at Chick a pea this past may. Todd was wonderful during all of the communication phases, booking and getting into the property. Upon arrival Todd...
    5 of 5 stars Reviewed May 20, 2014
    My husband and another couple went for a week of relaxation. This was the perfect home with all the amenities. The pool and outdoor sitting area is where we spent most of our...
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    Studio / 1 Bathroom / Sleeps 2
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    • Shared Outdoor Pool...
    • Air Conditioning
    • Parking
    • Satellite TV
    • Internet Access
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Elder access
    • x
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    About this property
    Room 2's pale shade of coral will continually remind you that you're staying in a tropical paradise. Step out onto the semi-private veranda overlooking the pool. Sit and relax, surrounded by the tropical vegetation that abounds on this magnificent island. An oversized shower in the private bathroom... View all property information
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    Key West, Florida Keys 33040
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    $265
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    1 / 32
    4.5 of 5 stars (5) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Satellite TV
    • Waterfront
    • Hot Tub
    • Sauna
    • Air Conditioning
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    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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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 2, 2015
    We loved our stay in Key West which was enhanced by the condo's location, views, lovely large heated pool and jacuzzi with views of Atlantic Ocean, our balcony with view of ocean...
    5 of 5 stars Reviewed May 30, 2014
    The vacation property is well worth the price. It's well maintain with beautiful views and perfect pool. Very spacious and quiet, perfect for a family. The condo is a 2 to 3...
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    4.5 of 5 stars (39) Very good
    10 Bedrooms / 6 Bathrooms / Sleeps 20
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    Amenities & Details
    • Waterfront
    • Hot Tub
    • Private Outdoor...
    • Satellite TV
    • Water Views
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 26, 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 February 4, 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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    5 of 5 stars (1) Excellent
    7 Bedrooms / 6 Bathrooms / Sleeps 18
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    • Deck
    • Washer
    • Internet Access
    • There Are Tennis...
    • Air Conditioning
    • Satellite TV
    • Watersports Nearby
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
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    • Elder access
    • ?
    About this property
    Our unique property consists of 3 suites (a total of 7 bedrooms and 6 baths) with 2 sparkling lagoon style dipping pools in one compound in the luxurious Casa Marina area of Old Town Key West. We can accommodate groups up to 18 guests. The breakdown of the 3 suites which are being rented... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 16, 2014
    So our stay was Friday - Tuesday in January … We rented the Hemingway suite then added additional rooms … Love Love Love this place !! can not say enough about the owners / and...
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    1 of 5 stars (1) Terrible
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Shared Outdoor Pool...
    • DVD Player
    • Hot Tub
    • Internet Access
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This popular island destination is the site of the only living coral reef in the coastal regions of the US. In addition to the marine life and water activities other features of Key West include natural preserves and unique land animals. Coconut Mallory Resort and Marina is located in Key West,... View all property information
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    Key West, Florida Keys 33040
    1 of 5 stars Reviewed April 3, 2014
    We booked this through Expedia (sorry trip Advisor). Check in began at 4 according to our printed information from Expedia. We arrived at 6:30--the office was closed--- it had...
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    4 of 5 stars (13) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (13) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Terrace
    • Balcony
    • Shared Outdoor Pool...
    • Gym
    • Linens Provided
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Bright, tropical colors and tile floors provide an island ambience to... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed February 27, 2014
    This unit has recently been refreshed and is very comfortable. It has everything you need to have a perfect vacation. The kitchen is well stocked, if you are inclined to do some...
    5 of 5 stars Reviewed March 8, 2013
    We were very happy with our condo. Everything was neat and clean. Living room furniture was outdated but would not stop from returning.
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