Owner Direct Vacation Rentals in Upper Sugarloaf Key

The Best Owner Direct Vacation Rentals in Upper Sugarloaf Key. Explore thousands of vacation home rentals, large cabins, and villas near Upper Sugarloaf Key

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From US $811

         

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10.0 (4 Reviews)

Villa

Ocean View with Pool, 4 bedroom Vila Near Key West

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Cudjoe Key

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New

From US $876

         

New

Villa

Beachfront Heated Pool Hot Tub Oceanview

• Air Conditioner
• Pet Friendly
• Pool

• Florida
• Cudjoe Key

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From US $1,097

         

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10.0 (1 Review)

Villa

Atlantic View Luxury Villa with Pool

• Parking
• Pet Friendly
• Pool

• Florida
• Cudjoe Key

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From US $304

         

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9.6 (2 Reviews)

House

Pelico Paradise

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sugarloaf Key

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New

From US $988

         

New

Villa

Eco Friendly Secluded OceanView Pool near Key West

• Air Conditioner
• Pet Friendly
• Pool

• 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 $458

         

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9.0 (346 Reviews)

House

Sugarloaf Key RV Resort & Cottages

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sugarloaf Key

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From US $451

         

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 $278

         

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9.8 (457 Reviews)

Hotel

Sugarloaf Key Hotel at KOA Resort

• Air Conditioner
• Parking
• Pool

• Florida
• Sugarloaf Key

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From US $405

         

9.0 (1 Review)

House

Oceanview's and heated pool in Cudjoe Key, FL

• Air Conditioner
• Parking
• Pool

• Florida
• Cudjoe Key

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From US $518

         

10.0 (200 Reviews)

House

Luxurious Oceanfront Home on Beach, Dock, Heat/Cool Pool, Kayaks, Bikes, Views!

• Air Conditioner
• Parking
• Pool

• Florida
• Cudjoe Key

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From US $2,804

         

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8.0 (1 Review)

House

Villa of the Setting Sun

• Air Conditioner
• Pool
• View

• Florida
• Sugarloaf 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 $313

         

7.4 (552 Reviews)

Cabin

Sugarloaf Lodge

• Air Conditioner
• Parking
• Pool

• Florida
• Sugarloaf 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 $1,197

         

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New

Villa

Oceanview Villa Heated Pool + Hot Tub

• Pet Friendly
• Security/Safety
• Child 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 $950

         

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New

Villa

Private Estate Pool Ocean View 20 minutes to Key West

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Cudjoe Key

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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 $580

         

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New

House

Starlight Serenity - Hideaway with Stunning Views

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sugarloaf Key

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From US $460

         

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New

House

Loggerhead Lagoon - Modern Waterfront Home

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sugarloaf Key

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From US $363

         

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New

House

Key Lime Time

• Air Conditioner
• Parking
• Pool

• Cudjoe Key
• Cutthroat Harbor Estates

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From US $301

         

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New

House

Parrotfish Pointe

• Air Conditioner
• Pool
• View

• Cudjoe Key
• Cutthroat Harbor Estates

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From US $923

         

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New

Villa

Eco Friendly Secluded OceanView Pool near Key West

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Cudjoe Key

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★ Pro Tip: Ownerdirect makes it easy to compare the best listings on Ownerdirect homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Ownerdirect homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Upper Sugarloaf Key.