Floridarentalvacations - Vacation Rentals in Upper Harbor Key

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From US $223

         

10.0 (25 Reviews)

House

Your Best Fishing And Relaxing Experience! 2/2 Waterfront Home

• Air Conditioner
• Parking
• TV

• Florida
• Little Torch 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 $327

         

9.6 (106 Reviews)

House

Tropical Island Paradise W/Open Water Views!

• Air Conditioner
• Parking
• Pool

• Florida
• Cudjoe Key

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From US $804

         

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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 $248

         

8.6 (260 Reviews)

Cottage

Old Wooden Bridge Resort and Marina

• Air Conditioner
• Parking
• Pet Friendly

• Big Pine Key
• Punta Brisa

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From US $265

         

9.4 (164 Reviews)

House

Comfortable Waterfront Vacation Rental minutes from key west w boat dock 35 ft

• Air Conditioner
• Parking
• Pool

• Florida
• Cudjoe Key

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From US $7,000

         

New

Apartment

Florida Keys /Big Pine Key/ Dear Haven

• Air Conditioner
• Parking

• Florida
• Big Pine Key

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From US $278

         

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9.8 (449 Reviews)

Hotel

Sugarloaf Key Hotel at KOA Resort

• Air Conditioner
• Parking
• Pool

• Florida
• Sugarloaf Key

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From US $233

         

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 $268

         

9.0 (143 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 $293

         

10.0 (12 Reviews)

House

"Canal-Front Paradise in Big Pine Key-Relax &Explore the keys"

• Air Conditioner
• Parking
• Pet Friendly

• Big Pine Key
• Port Pine Heights

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From US $430

         

8.8 (147 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 $314

         

9.6 (4 Reviews)

House

7 Seas Bring your boat. This is a pet friendly home. A pet fee and approval of your pet is required.

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Little Torch Key

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From US $548

         

10.0 (61 Reviews)

Cottage

Waterfront Cozy Cottage with Boat Ramp & Dock!

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Little Torch Key

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From US $344

         

10.0 (11 Reviews)

House

Beautiful, 2100 sq ft 3/2 w/ocean views & easy ocean & gulf access.

• Air Conditioner
• Parking
• Pet Friendly

• Cudjoe Key
• Cutthroat Harbor Estates

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From US $268

         

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 $570

         

New

House

Pool house with open water and sunset in the Florida Keys

• Air Conditioner
• Parking
• Pet Friendly

• Big Pine Key
• Doctor's Arm

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From US $261

         

9.8 (30 Reviews)

House

FREE KAYAKS & BIKES! Private Pool Home. Little Torch Key. Great Fishing Area.

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Little Torch Key

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From US $209

         

9.6 (4 Reviews)

House

Conch House on a Quiet Canal : Monthly Only

• Air Conditioner
• Parking
• TV

• Florida
• Little Torch 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 $396

         

10.0 (227 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 $495

         

10.0 (174 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 (155 Reviews)

House

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

• Air Conditioner
• Pool
• TV

• Florida
• Cudjoe Key

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★ Pro Tip: Floridarentalvacations makes it easy to compare the best listings on Floridarentalvacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Floridarentalvacations 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 Harbor Key.