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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.
    154 Matching Rentals in Key WestView all 317 rentals
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Bahamian Reed1 / 24
    (1)Average
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Top Of Duval- 6 Bedroom Penthouse1 / 26
    (17)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    The Meadows House1 / 19
    (23)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Bahama House1 / 24
    (27)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury rental with all the amenities you can ask for, Bahama House might just be right right vacation rental for you! Location, Location, Location! Totally gorgeous, this spacious house rental Key West is conveniently located on a quiet street in the heart of Old Town Key West around the corner...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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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
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Cable/satellite TV
    • Washer
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    Suitability
    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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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Tree House Old Town 2 Bedroom MONTHLY Rental1 / 16
    (7)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Grill
    • Air Conditioning
    • Porch
    • Outdoor Dining Area
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Washer
    • 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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    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
    • Grill
    • Wi-Fi
    • 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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    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
    • Wi-Fi
    • 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
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Grill
    • Cable/satellite TV
    • 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
    • Cable/satellite TV
    • Wi-Fi
    • 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
    • Cable/satellite TV
    • Parking
    • Washer
    • Air Conditioning
    • Patio
    • DVD Player
    Suitability
    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
    Suitability
    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
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    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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    Location Information
    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
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • 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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    Duval Square1 / 22
    (49)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There's no more perfect place to practice the art of tropical vacationing than this professionally decorated, two-story townhome, which features two bedrooms, two and a half baths, a private deck with private hot tub, and a master bedroom balcony. A short walkway flanked by lush gardens leads to a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Starlight Siesta ~ Weekly Rental1 / 10
    (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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Balcony
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Key West Dreamin' ~ Weekly Rental1 / 20
    (12)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Patio
    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    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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    Kemp House1 / 25
    (20)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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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
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    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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    Tropical ~ Tranquility ~ Weekly Rental1 / 17
    (8)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real. Extraordinarily secluded 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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    Key West Wabi Sabi ~ Weekly Rental1 / 31
    (3)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof....
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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 Casa1 / 24
    (26)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Terrace
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious 3 bedroom apartment is located in Shipyard of Truman Annex, one of the most desirable Key West communities, close to Blue Heaven and Santiago's Bodega, one of Key West most popular restaurants. Beautiful and spacious Shipyard condo Key West, Key West Casa is one of only a few 3...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spa On Duval1 / 24
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful vacation rental is located in the heart of Old Town, close to everything Key West has to offer! 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,...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Twice as Nice ~ Weekly Rental1 / 17
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    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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    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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    Key West Seashell Cottage-1 block to Duval, spa1 / 16
    (46)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Forget that 'been there, done that' hotel room; enjoy the comforts of home in Old Town Key West at the Seashell Cottage. Located on a quiet lane, just 1 block to Duval Street, walk to the grocery store, restaurants, museums, beach, and 'Sunset Celebration'. The original local artwork throughout...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Cockadoodle Cottage ~ Weekly Rental1 / 10
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Patio
    • DVD Player
    Suitability
    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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Caroline House Estate ~ Weekly Rental1 / 35
    (9)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Heated)
    • Grill
    • Cable/satellite TV
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for two families wanting to vacation together or large groups. This is a large duplex home with a total of 5 bdrms and 3.5 bathrooms: One side has 3 bdrms (two rooms with queen, one room with 2 twins) + 2 baths. The other side has 2 bdrms (one room with queen, one room with 2 twins) + 1.5...
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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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    Key West Spa Villa ~ Weekly Rental1 / 22
    (7)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    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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    Family Reunion ~ Weekly Rental1 / 53
    (2)Very good
    9 Bedrooms, 10 Bathrooms, Sleeps 28 Quick View
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    • Washer
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Thinking about getting your extended family or friends together for a Key West vacation? This one-of-kind gated Key West vacation rental compound, with large private swimming pool in spacious landscaped tropical garden setting, could be the perfect place. Family Reunion Key West vacation rental...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 9 Bedrooms, 10 Bathrooms, Sleeps 28
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    Coral Villa1 / 24
    (11)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming, clean and nicely decorated vacation rental home is located in Coral Hammock, one of Key West newest communities, very close to restaurants, boating and water adventure! Located right in the middle of the action, Coral Villa is a beautiful Key West Florida townhome with 3-bedrooms...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Exclusive Key West Beach Front ~ Weekly Rental1 / 21
    (4)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rare, one-of-a kind designer luxury condominium located in an exclusive gated Key West beachfront property. The Exclusive Key West Beachfront vacation rental has breath taking views overlooking the ocean and natural aquatic bird sanctuary. A spacious ocean front balcony provides the perfect setting...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Nautical Dreams1 / 24
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In a small gated community this perfect cottage with a large private deck to allow all the privacy you would need to grill, dine and lounge. Here's the perfect spot for whatever you desire, parties or peace & quiet in a Florida vacation home Key West. This 2-bedroom 2-bath cottage is located in...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Villa Nouveau Key West ~ Weekly Rental1 / 38
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sometimes a Key West cottage that at first glance appears predictable from the outside, is full of abundant surprises when you walk inside. Villa Nouveau Key West vacation rental has an interesting story that attests to this truth. Once a prosaic 'shot-gun' style cottage, a modern redesign has...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • DVD Player
    • Sauna
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re craving a Key West beach accommodation with a bone fide front-line view to the sea, you know they’re not easy to come by. But in this pretty vacation rental condominium, By The Beautiful Sea, you can instantly gratify this need for sensational vistas from your own vacation rental terrace...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    A Tropical Tradition (Gallup Arms) ~ Weekly Rental1 / 10
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in one of Key West's original gated 'mini-compounds,' the Tropical Tradition vacation rental is a spacious 1990's three-story Key West town home providing an island living experience in a traditional tropical style - both inside and out. A lush tropical garden complete with large 40' X 16'...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Flower Power House ~ Weekly Rental1 / 29
    (2)Average
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Flower Power House 5 - 6BR (Sleeping Porch) 4BA Sleeps 12+ Boho beautiful, the free-spirited presence of the Key West Flower Power House has much more in common with the real Key West than the shiny hotels around town. Kindred to memories we share about ‘the good old days,’ this 1938 wooden house...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Penthouse On Duval ~ Weekly Rental1 / 40
    (11)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Parking
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfectly staged in the island's city center, this spectacular downtown Key West rental received a major renovation to become the fabulous Penthouse on Duval. This unique private Caribbean style penthouse is the perfect prescription for some lofty relaxation. Perched just above the fun and frolic...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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