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Vacation Rentals near Key West Intl Airport

3491 S Roosevelt Blvd, Key West, Florida 33040
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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 107 Rentals in Key West
    Sunrise Suite Key West 2 Bed Rooms 2 Full Baths1 / 18
    (94)Excellent
    0.5 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Top floor, two bedroom,two bath condo with private balcony,close to the Ocean1 / 47
    (4)Excellent
    0.5 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sunrise at Seaside Condo 2 Bedroom1 / 24
    (39)Very good
    0.5 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean1 / 19
    (17)Very good
    0.5 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    Reviewed February 22, 2019
    The condo was very nice. Clean and roomy! We had a wonderful time. Check in and out was simple and all directions were spot in
    Reviewed November 6, 2016
    Overall we were satisfied with our stay at this condo, but there were pros and cons. Pros: The layout was nice, almost like 2 separate hotel rooms joined by a shared kitchen...
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    About this property
    This two bedroom, two full baths condo with kitchen and private balcony, offers all the conveniences of your own home. There is one King bedroom, one Queen bedroom and one Queen size pull out couch in the living room. Kitchen is equipped with tableware for at least six guests. Pots, skillets, and...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Sunshine suit (2/2 apartment)1 / 25
    (2)Excellent
    0.5 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed April 19, 2021
    Booked last minute and luckily this apartment/ condo was open for the Saturday. We drove down from Miami and checkin time was 3:00pm but again , luckily we got in a hour earlier...
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    About this property
    Come to spend your Vacation in Key West Paradise! Stay with us! Enjoy the pool view! Our apartment is locating on the 4th floor at the Sunrise Suites Resort. We have 2 bedrooms and 2 bathrooms apartment with full kitchen. There is 2 king sized beds and 1 queen pull-out sofa beds in the apartment....
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.8 miles from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
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    About this property
    Private home located in New Town available for 28 day minimum rental. Beautifully landscaped yard with secure private back yard and pool. The home features a kitchen with all appliances and granite counter top. The master suite opens onto the pool deck and is furnished with a king size bed and...
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    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Truman Annex, two blocks from Duval1 / 35
    (74)Very good
    2.9 miles from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Balcony
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    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    'LOST SHAKER OF SALT' ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Pool1 / 14
    (130)Excellent
    2.5 miles from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Craig & Cindy Key West Truman Annex 212 Fleming House1 / 48
    (21)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    'Stone's Throw' ~ Beautiful home in a great location!1 / 17
    (11)Excellent
    2.6 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    BARGAIN RATES! Pool, wifi, renovated 2/2 1/2 private courtyard.1 / 50
    (79)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    2022 IS THE FINAL YEAR.  Giving it to a vacation rental company for 2023.1 / 39
    (101)Excellent
    1.1 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
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    Pet friendly
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.8 miles from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Tropical Key West Get Away1 / 33
    (111)Very good
    1.7 miles from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Secret Villa I * Old Town with Private Pool, close to Duval!1 / 25
    (89)Excellent
    2.5 miles from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    SUMMER 2023 COMING FAST - BOOK NOW & SAVE1 / 25
    (126)Very good
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval!1 / 24
    (143)Excellent
    2.3 miles from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    TRUMAN ANNEX - FOUNDRY 71 / 20
    (33)Excellent
    2.9 miles from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Apple of Your Eye in Paradise (Truman Annex)!1 / 24
    (78)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Attitude Key West (2 Bikes and Wireless Internet)1 / 51
    (146)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Completely renovated in 2016! Galleon Resort Efficiency Historic District1 / 33
    (45)Very good
    2.8 miles from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!1 / 34
    (10)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed April 26, 2021
    We stayed at Shipyard 206-7 by Cindy & Craig in October 2020 for 7 nights. The location is prime; not too far from Duval and all the fun activities, but def far enough away...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Key West Golf Club - Completely Renovated - Tree House Too.1 / 19
    (11)Excellent
    1.9 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.4 miles from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    1.8 miles from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Great location! Everything one would need. 3 month minimum1 / 13
    (6)Excellent
    2.1 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West1 / 37
    (70)Excellent
    2.7 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!1 / 25
    (72)Excellent
    2.5 miles from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin1 / 50
    (32)Excellent
    2.6 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    'OFF CALL' ~ Rustic, Nautical Decor With King Master Suite & Heated Pool!1 / 21
    (62)Very good
    1.7 miles from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Harbour Place 115 in Truman Annex Key West1 / 45
    (66)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    2022 IS THE FINAL YEAR.  Giving it to a vacation rental company for 2023.1 / 39
    (31)Excellent
    1.2 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Downtown Nassau Oasis 1 Bedroom Townhouse steps to Duval1 / 27
    (143)Very good
    2.4 miles from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
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    Key West, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.5 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Welcome to SALT PONDS SANCTUARY! This beautifully adorned condo on the third floor of the Salt Ponds Condominium Complex in Key West boasts a private balcony to view the sunset while sipping your favorite cocktail. You are minutes from Duval Street where you can sample the many restaurants and...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Downtown Location in Historic District-No Contact Check-In1 / 37
    (44)Very good
    2.1 miles from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Azure Morning- Oceanfront, near Marina, Pool & Jacuzzi1 / 24
    (98)Excellent
    2.0 miles from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    'Oceanside Oasis' * Kings Pointe: Direct Ocean Views & 3 BR'S1 / 32
    (91)Excellent
    2.0 miles from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Penthouse Level Ocean Views-  Live the Dream1 / 41
    (146)Very good
    1.1 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.5 miles from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Boli Townhouse - Luxury Rental in gated Truman Annex1 / 51
    (132)Excellent
    2.9 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.7 miles from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Ocean Breezes, Morning Sunrises, Excellent nightly rental condo on the ocean.1 / 49
    (88)Very good
    1.1 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Smuggler's Den: 3 Blocks to Downtown, Walk to Restaurants & Galleries Hot Tub1 / 29
    (4)Excellent
    2.4 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.1 / 44
    (127)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 23, 2021
    I have booked STARFISH in the past and have booked it again, and will not hesitate to book this property whenever my future travels include Key West, Florida. The interior of...
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    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Catherine House: A charming Old Town Key West cottage1 / 29
    (161)Excellent
    2.3 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    The Grande Vista: 2  BR, 2  BA Condominium in Key West, Sleeps 61 / 42
    (79)Very good
    1.1 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.7 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Attitude Key West at the Beach, 2 Bikes and Internet, Pool, Whirl Pool, Sauna1 / 51
    (198)Excellent
    1.2 miles from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Enjoy More Privacy in a Truman Annex End Unit Townhome1 / 24
    (121)Excellent
    2.8 miles from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
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    Suitability
    Pet friendly
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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