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Key West Cottages

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    44 Matching Rentals in Key WestView all 851 rentals
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    Casa Manana Conch Cottage1 / 41
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Two Bedroom Historic Hideaway Olivia Retrea Private Pool  Key West- Monthly1 / 26
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Southernmost Retreat- 1 Block from Duval1 / 99
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    About us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique.... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both rooms to accommodate up to 4....
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Satellite TV
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    About this property
    This newly renovated unit is located just two blocks from world famous Duval Street surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway. The bungalow features an one level open space living/dining area, full kitchen and a spacious...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    ROBERT FROST COTTAGE1 / 10
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Over 100 miles from mainland Florida and the southernmost point in the United States, Key West has attracted numerous artists and writers, including Ernest Hemingway, Wallace Stevens, Ralph Ellison, Elizabeth Bishop, Tennessee Williams, Robert Frost, and James Merrill. At 410 Caroline Street is...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Atlantis House Master Suite1 / 22
    (21)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
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    About Us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique Guesthouse with only 2 suites... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Chick-a-Pea's Cottage: Pet-Friendly with Fenced Yard! Parking & Private Pool1 / 28
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    Pet friendly
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    About this property
    The house is a traditional Key West cottage that has undergone a complete renovation in 2012. The charm and historic features have been retained, while all the luxuries of today have been added. There is a master bedroom, with king bed and full bath, on the first floor. Additionally, there is a...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    Pet friendly
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    About this property
    Brand New! Solaris Cottage Garden, located on one of Key West most private slow lanes, and is a Bohemian Dream!. Perfect for a couple or single guest ready to explore all that Key West has to offer! This unique vacation rental just completed renovation December 1st 2016! All new furnishings and...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Ann Street Cottage: A bright and airy home near Duval Street1 / 24
    (47)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Patio
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    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer....
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Ann Street Tranquility:  A cozy and peaceful cottage1 / 16
    (49)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
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    Pet friendly
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    This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Ann Street Gardens1 / 25
    (55)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    END OF SUMMER DISCOUNT! 10% OFF already discounted prices for open dates AUGUST - SEPTEMBER 2017! Please call our office for details. (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect....
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. <BR><BR>Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    'TIDES ON SIMONTON' - Perfect location!1 / 24
    (8)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Solaris Garden Cottage: Historic Old Town Lane, 14 minute walk to Beach!1 / 24
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Seagull Suite - Downtown Room w/ 3 Hot Tubs On Site. Steps to Duval St!1 / 24
    (16)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    TROPICAL COTTAGE 30 DAY MINIMUM1 / 11
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Pete's West Cottage steps from Duval1 / 22
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Colony Caylpso - A quaint 1 Bedroom Cottage just two blocks to Duval1 / 22
    (9)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sea Breeze Cottage- in Beautiful Truman Annex1 / 24
    (22)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Downtown Location in Historic District1 / 20
    (7)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Key West, Florida Keys 33040
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Southernmost Sanctuary - 6 Private Rooms 1 Block from Duval St - 3 Hot Tubs1 / 16
    (2)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 24
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    Downtown Cottage in Historic District1 / 23
    (14)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 1 Bathroom, Sleeps 4
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    POOLSIDE * TROPICAL VILLAGE - Studio for 2 w/ Shared Pool. Close to ATL Ocean1 / 24
    (32)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Heron Suite - Old Town Studio - 3 Hot Tubs - Grill - One Block from Duval St1 / 24
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Truman * Duval- Old Town KW Home Just A Hop-Skip-And-Jump To Duval St.1 / 24
    (33)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    November

    Additional Key West Info

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    • Local time: 09:17 AM (EDT)
    • Peak travel: February - April
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