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Key West House Rentals

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    159 Matching Rentals in Key WestView all 330 rentals
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    Coral Villa1 / 24
    (11)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West Found1 / 24
    (32)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Penthouse On Duval ~ Weekly Rental1 / 20
    (11)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Wind Swept1 / 24
    (2)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
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    WIND SWEPT: Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States. This lovely 2 bedroom 1.5 bath Key West townhome is freshly painted and newly furnished. Enter the open and airy...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Casa Grande1 / 24
    (4)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa Grande...
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Vintage Luxury Cottage ~ Weekly Rental1 / 11
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Without a doubt, one of the rarest private Key West vacation cottages available. Situated in one of the most requested locations in Old Town Key West, this luxury renovated turn-of-the-century Vintage Luxury Cottage vacation rental is hidden just off upper Duval Street in Old Town. Enter the gate...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cockadoodle Cottage ~ Weekly Rental1 / 30
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West cottage architecture has been thoroughly 'time-tested' in 'island life and culture' in this somewhat infamous little wooden 'cigar maker's' cottage located on famous Duval Street, at the 'classier upper-end.' Since its original construction in the early 1900's this note-worthy Cockadoodle...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key Lime Pie1 / 22
    (7)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    KEY LIME PIE: One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town. Refurbished with updated kitchen cabinets, countertops, and appliances. On the first floor you will find the living room, kitchen, master bedroom and bathroom. On the second...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Heavenly Hideout at Rainbow's End ~ Weekly Rental1 / 33
    (9)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time. But when you rent this Heavenly Hideout at Rainbow’s End, you’re spot on, and you can do exactly that. This tropically...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • DVD Player
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    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this inviting Key West condo your home base when you come to Florida, and prepare yourself for a sunny, fun-filled, and convenient getaway with family or friends. Located right near the water's edge, this home makes it easy for you to partake of the sunny, sandy beach whenever you like....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Balcony
    • DVD Player
    • Terrace
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CORAL BREEZE (monthly rental): Imagine yourself living with the vibrant golf course greens in your backyard and cool tropical breezes wafting your way. Coral Breeze has that and more. Two bedrooms share the full bath upstairs. Kitchen, dining, half bath and living room space in an open floor...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Key West home with boating and private swimming pool! Lovely, well appointed home, remodeled, granite and stainless appliances, 2 bedrooms, each with ensuite baths, 3 baths, tile and wood floors throughout. Open living and kitchen, living room and master bedroom opens to swimming pool and boating...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    The Hemingway1 / 25
    (27)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Balcony
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    • Private Outdoor Pool (Heated)
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE HEMINGWAY -- A beautiful 2 bedroom 2 bath Florida Keys rental home located in the private, gated community of Truman Annex. An ideal location only 2 blocks from famous Duval Street and the attractions of historic Old Town Key West. You can walk or bike to restaurants, nightlife,...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Blackbeard's Treasure - MONTHLY Rental (30 night min.)1 / 21
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Grill
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water's edge has been quintessentially transformed into Old Town Key West's most...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building. Perched among mature tropical trees, the 1200 square foot 2nd floor flat is situated on a quiet road...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On an island full of resplendent Victorian architecture, the trend toward minimalist design has made its mark. This 2-story tropical luxury home is a ubiquitous example of this, an ingenious melding of classic Old Town Key West architecture with contemporary pared-down design. Created by connecting...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    On Hemingway's Rounds ~ Monthly Rental1 / 14
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Private Garden
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views. The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge. Fishing and diving just steps outside your door. Then at night, Key West is...
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    Location Information
    Key West, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Private Garden
    • Patio
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Strikingly set in the oft-missed Key West mid-town neighborhood, we find Island Elegance, making a classical curbside statement with its craftsman-colonial architecture, lush mature tropical landscaping, and white picket fencing. Built in 2005, the design of this home incorporates the timeless...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    When I went to preview this townhome called Cabana Boheme, I was intrigued by the name. And so it was fitting to its nom de plume, that I drive the 10 blocks in our hand-painted conch cruiser truck, transformed into rolling art by local mural artist Rick Worth. Key West is like that, as much a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Seaport Treasure Estate ~ Monthly Rental1 / 34
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Washer
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    • Cable/satellite TV
    • Ocean Views
    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    While you won’t need a treasure map to find this exclusive resort-style estate, you’ll know you’ve discovered a rare island gem from the moment you walk through the private gates. Hidden by white picket fences and mature tropical landscaping, this spacious Seaport Treasure Estate is cleverly...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    Hemingway's Library – MONTHLY Rental1 / 20
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    • Grill
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sensational vacation home provides three bedrooms, two and a half baths, pool, and a downtown location yet manages to create a serene, get-away-from-it-all feel. Called Hemingway's Library, the residence maintains the mystique of the island's most famous author by way of books, pictures, and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Hot Tub
    • Air Conditioning
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    • Patio
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Without a doubt, this vacation-defining residence will become as much a part of your holiday memories as the island of Key West itself. Its two-story classic Conch architecture, centrally located in Old Town, includes two spacious master bedrooms, two full en-suite baths, one half bath, a large...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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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 Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Hot Tub
    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Children's Pool
    • Cable/satellite TV
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfectly positioned on Sunset Key, ‘the islands island,’ the Ultimate Key West Beach House ~ Sunset Key VIP, is within 500 yards off-shore of the ‘main island’ of Key West. A splendid view gazing toward Mallory Dock and the famous sunset celebration, this one-of-a-kind waterfront property offers a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Cable/satellite TV
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Classic romantic 1800’s Key West architecture has inspired a superbly executed renovation of this extraordinary historic Victorian estate. Displaying a perfected cosmopolitan flair, the owner / designer has artfully intertwined a look-back into architectural history with a sophisticated...
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    • Hot Tub
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Crowner's Jewel1 / 24
    (35)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CROWNER'S JEWEL: Experience the finest in vacation home rentals in Key West Florida when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome in the heart of the exclusive gated community of Truman Annex. New owner has added lots of upgrades to make you feel welcome in his new...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Waterfront
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3000 SF, 3BDR, 2.5BATHS, SLEEPS 6 Treat yourself to a dream vacation in our beachfront residence on the private island of Sunset Key, located in the middle of Key West Harbor. Our tastefully designed upscale villa has beautiful ocean views, private pool, and 2 hot tubs for our guests to enjoy. It...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Twice as Nice ~ Weekly Rental1 / 17
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In this case... 'Two is definitely better than One'! A rare set of early 1900's 'twin-cigar maker's cottages' perched on the southern end of famous Duval Street. The Twice As Nice vacation rental is at once adorable and elegant and a perfect solution for a discerning group who want to lodge...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Key West Spa Villa ~ Weekly Rental1 / 22
    (7)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Washer
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites. Opposites attract...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Parking
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    TROPICAL CASITA (Monthly Rental) It is rare to find a true jewel like Tropical Casita, nestled in a sweet little spot amid lush landscaping and secluded tranquility. Upon entering this gated residence you will immediately feel the ease of the islands as you are greeted by the shimmering private...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Key West Dreamin' ~ Weekly Rental1 / 40
    (12)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Patio
    • DVD Player
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants the Florida Keys has to...
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    Location Information
    Key West, Florida Keys 33042
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New 1,500 sq. ft. townhouse with 2 large bedrooms with king beds, 3 full bathrooms plus covered deeded parking for your car. Fully equipped kitchen. Sleeps up to 6 comfortably as the downstairs living room has a queen sleeper and full bath. Luxury furnishings and appliances throughout make this...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'In-the-know' travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval,...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Spa On Duval1 / 24
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SPA ON DUVAL - Is a tropical two story, 2 bedroom 2.5 bath Old Town Key West condo located in the rooftop community of Duval Square where you only have to walk downstairs to great restaurants, speciality shops and the action of Duval Street. Spa On Duval is truly a Key West experience to enjoy!...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pavilion Villa ~ Weekly Rental1 / 20
    (8)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a half-block off Duval St. in Old Town Key West. I first visited this private home when it was featured on the prestigious Garden Home Tour of Key West which opens a few select...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island. Enjoy full use of direct TV channels, free current...
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    Location Information
    Key West, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Grande Dame Key West - 'The Watson House' ~ Weekly Rental1 / 38
    (10)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grande Dame Key West – (The Watson House) vacation rental estate is an impeccably detailed 3-story Classic Folk Victorian home with 7 bedrooms and 7 bathrooms. An award winning renovation of this stately Victorian mansion has achieved an impressive balance of timeless charm, classic elegance, and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 16
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Grill
    • Washer
    • DVD Player
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this cozy and chic Key West cottage your home away from home for your next Florida vacation, and revel in a private pool, deck, and covered back porch, as well as close proximity to the beach. And the real bonus: you can bring your favorite canine friend along, too. You'll be situated only...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Patio
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This genuine Key West combo of our Private Pool Garden Villa plus a classy private studio cottage that adjoins the property next door, can be your very own get-away for a week or more. When rented together, we call the property the Lazy Iguana. Off-the-beaten path of most tourist homes and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Wi-Fi
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    COCONUT COTTAGE -- Adorable, affordable, and near all the action.... You bet! Coconut Cottage is the perfect escape for a couple or singles looking to get away from it all in paradise… Located in a quiet neighborhood of Old Town Key West, this Key West vacation rental one bedroom two bath...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    The Caroline House Estate ~ Weekly Rental1 / 105
    (8)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen. An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Down Island Digs ~ Weekly Rental1 / 14
    (9)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Caribbean Cottage ~ Duval Street Key West ~ Weekly Rental1 / 28
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Washer
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they'll say hi to one another even if they've never met. This is your neighborhood during...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Starlight Siesta ~ Weekly Rental1 / 30
    (1)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cleverly hidden from view at the end of a narrow island urban lane that intersects with downtown Duval Street, this Starlight Siesta vacation rental encompasses the rear half of the Key West penthouse property known as Penthouse On Duval. Perfectly staged in the island's city center, this...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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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
    • Cable/satellite TV
    • 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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 11 Bedrooms, 11 Bathrooms, Sleeps 24
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Washer
    • Waterfront
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy some of the great back country fishing the Lower Keys has to offer! Welcome to Bonefish Lodge, an upscale, tastefully furnished, 2 bedroom, 2 bathroom duplex on Big Coppitt Key. This home is located on a deep canal just minutes from Snipe Point and the gulf, or out front to the Atlantic...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Truman House1 / 20
    (20)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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