Top Winter Vacations - Vacation Rentals in Florida Keys Beaches

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From US $1,706

         

10.0 (14 Reviews)

House

Palm - Beach Houses Key West

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sugarloaf Key

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From US $313

         

7.4 (552 Reviews)

Cabin

Sugarloaf Lodge

• Air Conditioner
• Parking
• Pool

• Florida
• Sugarloaf Key

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From US $111

         

8.2 (1008 Reviews)

Hotel

Sugar Loaf Lodge

• Air Conditioner
• Parking
• Pool

• Florida
• Sugarloaf Key

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From US $2,430

         

10.0 (10 Reviews)

House

Azucar - Beach Houses Key West

• Air Conditioner
• Parking
• TV

• Florida
• Sugarloaf Key

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From US $1,395

         

New

House

Bungalows Beach Rental Key West - Lighthouse

• Air Conditioner
• Parking
• Pool

• Florida
• Sugarloaf Key

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From US $876

         

10.0 (9 Reviews)

House

Luxurious Oceanfront 5BR Property with heated Pool & Waterfall

• Air Conditioner
• Parking
• Pet Friendly

• Key West
• Bay Point

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From US $330

         

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New

House

Coral Queen Palm

• Air Conditioner
• Wheelchair Accessible
• Balcony/Terrace

• Key West
• Bay Point

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From US $469

         

10.0 (6 Reviews)

House

PARADISE on Sugarloaf Key! 704-650-8105 Summer and Fall low rates.

• Air Conditioner
• Parking
• Pet Friendly

• Sugarloaf Key
• Sugarloaf Shores

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From US $241

         

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New

House

Waterfront Key West Oasis with Float Dock!

• Parking
• View
• Balcony/Terrace

• Key West
• Bay Point

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From US $884

         

10.0 (4 Reviews)

House

Your own Private Resort! 50ft Dock on Canal w/Pool, Tiki and RV Hookup!

• Air Conditioner
• Parking
• Pet Friendly

• Key West
• Bay Point

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From US $458

         

10.0 (4 Reviews)

House

Discounts are available for extended summer rentals.

• Air Conditioner
• Parking
• Pet Friendly

• Sugarloaf Key
• Sugarloaf Shores

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From US $550

         

10.0 (3 Reviews)

House

Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Dining & Pet Friendly!

• Air Conditioner
• Pet Friendly
• Pool

• Sugarloaf Key
• Sugarloaf Shores

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From US $584

         

10.0 (2 Reviews)

House

$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, Dock & Pet-Friendly!

• Air Conditioner
• Pet Friendly
• Pool

• Florida
• Sugarloaf Key

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From US $1,983

         

9.8 (28 Reviews)

House

Florida Keys Beach Getaway

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sugarloaf Key

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From US $727

         

9.8 (14 Reviews)

House

Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!

• Air Conditioner
• Pet Friendly
• Pool

• Sugarloaf Key
• Sugarloaf Shores

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From US $362

         

9.8 (8 Reviews)

House

Sunset Bay: Spacious 5BR Getaway, Dockage, Heated Pool, Dog OK, Stunning Views & Minutes to Key West

• Air Conditioner
• Pool
• TV

• Key West
• Bay Point

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From US $1,334

         

9.6 (11 Reviews)

House

The Lighthouse - Beach Houses Key West

• Air Conditioner
• Parking
• Pool

• Florida
• Sugarloaf Key

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From US $2,284

         

9.6 (8 Reviews)

House

The Hemingway - Beach Houses Key West

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sugarloaf Key

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From US $345

         

9.6 (8 Reviews)

House

Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe

• Air Conditioner
• Parking
• Pet Friendly

• Sugarloaf Key
• Sugarloaf Shores

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From US $238

         

9.4 (8 Reviews)

House

30% Discounted Rate-Waterfront-Open Water View-Pool-Dock-Kayaks-Parking

• Air Conditioner
• Parking
• Pool

• Key West
• Bay Point

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From US $634

         

9.4 (6 Reviews)

House

Key West Beach House with heated pool, tiki, and dock.♿︎

• Air Conditioner
• Parking
• Pet Friendly

• Key West
• Bay Point

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From US $1,235

         

8.4 (7 Reviews)

House

Beach Getaway in the Florida Keys

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sugarloaf Key

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From US $3,276

         

8.0 (2 Reviews)

House

Hammock House - Beach Houses Key West

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sugarloaf Key

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From US $149

         

8.0 (1 Review)

House

Fish Camp | Old Florida canalfront getaway close to Key West

• Air Conditioner
• Parking
• Pet Friendly

• Key West
• Bay Point

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