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Key West Vacation Rentals

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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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    Coral Hammock 34- 3 Bedroom Townhouse with a Shared Pool1 / 23
    (62)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Penthouse On Duval ~ Weekly Rental1 / 20
    (10)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    'LOST SHAKER OF SALT' ~ Pet Friendly, 40' Private Pool, Two Blocks from the Fun!1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    About this property
    Stay in a beautifully restored Century Old Conch Home by the Southernmost Point, the beach and Duval Street. Enjoy the nightlife of what Key West has to offer without the need to drive or take a taxi. No detail was left undone through- out this home featuring lots of dade county pine and...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Hot Tub
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    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Overlooking Famous Duval St. Key West, FL1 / 15
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Claude Monet Suite - Artsy Old Town Studio Close To Everything1 / 21
    (41)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Craig & Cindy's Truman Annex Key West Property1 / 24
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Beach Club #408 - Unique Oceanfront living1 / 24
    (13)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Key West, Florida Keys 33040
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    'STARS & STRIPES' ~ Magnificent Home In The Heart of Old Town!1 / 24
    (2)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Balcony
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    Key West, Florida Keys 33040
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    Club Cuba Suite at Top of Duval1 / 23
    (8)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    • Private Outdoor Pool (Heated)
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    About this property
    Whether you want to connect or reconnect with the island paradise of Key West, this residence, aptly named The Sanctuary, is a dream destination. Its L-shaped architectural design centers around a temperature-controlled pool, built-in hydro massage spa, graceful waterfall, and outdoor rain shower....
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    Key West, Florida Keys 33040
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Butterfly Garden ~ Monthly Rental1 / 10
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Yard
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    About this property
    Completely hidden from the street, this recently redecorated garden flat provides you with two private entrances off a large gated manicured garden. Your own private expansive covered bricked front porch spans the width of the garden right out the front door and leads to a beautiful meditation...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Very Rare- Ocean Breeze Suites-3 Bd, 3 Bath with loft  Sleeps 101 / 24
    (23)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Key West, Florida Keys 33040
    Condo/Apartment - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Luxury 2 Bedroom with Full Kitchen - Sleeps 5 - Walk to the Beach & Nightlife1 / 24
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Casa Atlantica: A studio condo on the Atlantic shore of Key West1 / 10
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Pet friendly
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    'SOUTHERNMOST BELLE' ~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!1 / 24
    (2)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    New 35' Downeast Boat in Beautiful Key West!1 / 8
    (1)Excellent
    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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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Hemingways Atlantic Retreat C3391 / 24
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Potter`s Cottage: Sleeps 5, Walk to the Beach & Nightlife, Private Dip Pool!1 / 24
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Outdoor Pool (Unheated)
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Harbour Place 115 in Truman Annex Key West1 / 23
    (15)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    'This Place Has Everything!' - says houseguest JDA1 / 16
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    TOTALLY REDECORATED/BARGAIN RATES Truman Annex 2/2 1/2 WIFI, 2 blks to Duval St.1 / 24
    (5)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    737 The Place, a  Monthly Rental Old Town Key West1 / 15
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Reasonable rates, best for couples and small families, Key West, Private, gated property in Historic Old Town Key West. Fishermen will love smoker grille for their catch. Newly refurbished, tropical furnishings, private deck. Large kitchen with full range and oven, microwave, and toaster oven....
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    About this property
    Enjoy a classic Key West vacation at this charming 1BR apartment in a restored 1920's conch house. This prime Old Town location is just a short walk from Duval Street, the historic seaport, beaches, dining, and one-of-a-kind shops. Guests enjoy use of the heated pool. ABOUT THE APARTMENT This...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This is a luxury 43 foot yacht. Everything is first class. Full galley. Very clean. Brand new. Great friendly marina. Lots of artists and creative people work and live here. Great restaurant the Hogfish Bar and Grill is right next door. Six beds behind 4 doors and 2 baths. Three AC units....
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pineapple Cottage/526 Southard St1 / 23
    (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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    If you have had your fill of hotels and the street scenes of downtown Key West and you don't want to spend another minute on a boat loaded with people but do want to get out on the water, then S/V Tortuga may be the perfect solution for you. Tortuga Sailing Adventures offers a unique, totally...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    This is a House Boat that is 45 feet long and 18 feet wide two story. The Boat House is located Sunset Marina over looking the Gulf Of Mexico. Fisherman paradise and couples paradise. You are just minutes for all of Key West excitement. The marina is very quite and the water is crystal clear. You...
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    Location Information
    Key West, Florida Keys KEY WEST FL 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Shipyard Palms: A first floor condo in the Shipyard of Truman Annex1 / 13
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    KEYLIME COTTAGE - 1 Block From All The Duval Action! Pvt Parking, Shared Pool1 / 24
    (24)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Patio
    • Balcony
    • Grill
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    • Terrace
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Meeting Point - Key West ~ Weekly Rental1 / 54
    (2)Average
    11 Bedrooms, 11 Bathrooms, Sleeps 24 Quick View
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    • Patio
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    • Grill
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Meeting Point – Key West is by-far the most spacious and classically elegant vacation rental property on the island. Situated in the heart of Old Town, there is nothing else like it. If you’re looking for luxury and plenty of room, The Meeting Point is the grandest vacation rental in Key West,...
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    Key West, Florida Keys 33040
    Rental Home - 11 Bedrooms, 11 Bathrooms, Sleeps 24
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Terrace
    • Satellite TV
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Tom's Parrot Perch:  Gut Renovation, Ocean View, Heated Pool, Close to Beach1 / 24
    (36)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    • Sauna
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    • Shared Outdoor Pool (Unheated)
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    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Luxury ~ Weekly Rental1 / 29
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    • Private Yard
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Genuine ‘old-world’ charm meets modern tropical luxury in this wonderful historic island home. Built of original glistening clear heart pine from floor to 12 foot ceiling, the immaculate interior rooms radiate a warm and magical feel that would be nearly impossible to replicate by modern builders....
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Housekeeping Included
    • Ocean Views
    • Sauna
    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GALLEON RESORT PENTHOUSE with LOFT - 2BR/2BA + GREAT VIEWS OF THE GALLEON MARINA, SEAPORT & OCEAN 5th FLOOR CONDO RENTAL / SLEEPS 8 / Unit F-53 / ***Only available Week 2 (Jan 13-20, 2018) / 1 Master King - 2 Guest Room Twins - 2 Loft Twins - 1 Queen pullout BEAUTIFULLY LANDSCAPED OCEANFRONT...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Grenada Suite Treat your self to Key West sun and fresh air!1 / 24
    (8)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Terrace
    • Balcony
    • Satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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