Florida Rental Vacations - Vacation Rentals in Upper Sugarloaf Key

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From US $259

         

8.6 (164 Reviews)

Cottage

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Cudjoe Key

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From US $304

         

|

9.6 (2 Reviews)

House

Pelico Paradise

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sugarloaf Key

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From US $983

         

|

10.0 (1 Review)

Villa

Atlantic View Luxury Villa with Pool

• Parking
• Pet Friendly
• Pool

• Florida
• Cudjoe Key

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From US $295

         

9.0 (145 Reviews)

Cottage

Quaint cottage, pool, dockage just minutes to Key West!

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Cudjoe Key

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From US $804

         

|

1.0 (1 Review)

Villa

Luxury OceanView Friendly Villa Near Key West

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Cudjoe Key

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From US $630

         

New

House

Starlight Serenity - Hideaway w Stunning Views

• Parking
• Pet Friendly
• Balcony/Terrace

• Florida
• Sugarloaf Key

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From US $459

         

8.8 (148 Reviews)

House

Cudjoe Cottages, swimming pool, just 20 miles from Key West

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Cudjoe Key

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From US $311

         

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New

House

Red Grouper Getaway

• Air Conditioner
• Parking
• Pet Friendly

• Cudjoe Key
• Cutthroat Harbor Estates

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From US $278

         

|

9.8 (457 Reviews)

Hotel

Sugarloaf Key Hotel at KOA Resort

• Air Conditioner
• Parking
• Pool

• Florida
• Sugarloaf Key

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From US $289

         

8.6 (119 Reviews)

Cottage

Charming cottages, dockage, pool, just minutes to Key West

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Cudjoe Key

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From US $413

         

10.0 (9 Reviews)

House

Waterfront home with a large dock, pool, and deck area. Can accommodate pets.

• Air Conditioner
• Parking
• Pet Friendly

• Cudjoe Key
• Cudjoe Gardens

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From US $420

         

10.0 (228 Reviews)

House

Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

• Air Conditioner
• Parking
• Pool

• Florida
• Cudjoe Key

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From US $506

         

10.0 (175 Reviews)

House

Oceanside home, dock,kayaks,bikes,pool,fishing,109

• Air Conditioner
• Parking
• Pool

• Florida
• Cudjoe Key

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From US $549

         

10.0 (156 Reviews)

House

Oceanside home, dock,kayaks,bikes,pool,fishing,111

• Air Conditioner
• Pool
• TV

• Florida
• Cudjoe Key

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From US $808

         

10.0 (41 Reviews)

House

Latitudes - Ocean front with salt water pool.

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Cudjoe Key

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From US $196

         

10.0 (15 Reviews)

House

Getaway to the Quiet Florida Keys

• Air Conditioner
• Parking
• TV

• Cudjoe Key
• Cudjoe Gardens

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From US $330

         

10.0 (12 Reviews)

Cottage

Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sugarloaf Key

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From US $383

         

10.0 (11 Reviews)

House

Oceanfront Home With Large Private Deck with boat dockage

• Air Conditioner
• Parking
• Pet Friendly

• Cudjoe Key
• Cutthroat Harbor Estates

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From US $335

         

10.0 (8 Reviews)

House

Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Cudjoe Key

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From US $394

         

10.0 (7 Reviews)

House

The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!

• Air Conditioner
• Pet Friendly
• Pool

• Cudjoe Key
• Cutthroat Harbor Estates

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From US $324

         

10.0 (7 Reviews)

Cottage

Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sugarloaf Key

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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 $536

         

10.0 (5 Reviews)

House

Amazing waterfront home with private beach, dock, pool, WiFi & outdoor kitchen

• Air Conditioner
• Parking
• Pool

• Cudjoe Key
• Cutthroat Harbor Estates

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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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