241+ Vacation Rentals Near Upper Sugarloaf Key |
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  3. Sugarloaf Key
  4. Upper Sugarloaf Key

Bigpineresortcottages - Vacation Rentals in Upper Sugarloaf Key

Property Image From $176
         

8.6 (163 Reviews)
Cottage
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $304
         

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9.6 (2 Reviews)
House
Pelico Paradise
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $862
         

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10.0 (3 Reviews)
House
195 m² House ∙ 5 bedrooms ∙ 12 guests
  • 2098 ft² House
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $888
         

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10.0 (1 Review)
Villa
Atlantic View Luxury Villa with Pool
  • Parking
  • Pet Friendly
  • Pool

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Property Image From $235
         

9.0 (142 Reviews)
Cottage
Quaint cottage, pool, dockage just minutes to Key West!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $804
         

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1.0 (1 Review)
Villa
Luxury OceanView Friendly Villa Near Key West
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $488
         

10.0 (3 Reviews)
House
111 m² House ∙ 2 bedrooms ∙ 6 guests
  • 1194 ft² House
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $278
         

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9.8 (438 Reviews)
Hotel
Sugarloaf Key Hotel at KOA Resort
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $356
         

8.8 (146 Reviews)
House
Cudjoe Cottages, swimming pool, just 20 miles from Key West
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $311
         

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New
House
Red Grouper Getaway
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $639
         

10.0 (2 Reviews)
House
279 m² House ∙ 5 bedrooms ∙ 12 guests
  • 3003 ft² House
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $111
         

8.2 (1002 Reviews)
Hotel
Sugar Loaf Lodge
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $242
         

8.6 (119 Reviews)
Cottage
Charming cottages, dockage, pool, just minutes to Key West
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $811
         

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10.0 (3 Reviews)
Villa
Ocean View with Pool, 4 bedroom Vila Near Key West
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $525
         

10.0 (9 Reviews)
House
Sunset view from pool and deck area. Dock includes lift. Can accommodate pets.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $458
         

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9.0 (321 Reviews)
House
Sugarloaf Key RV Resort & Cottages
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $384
         

10.0 (227 Reviews)
House
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $2,804
         

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8.0 (1 Review)
House
Villa of the Setting Sun
  • Air Conditioner
  • Pool
  • View

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Property Image From $482
         

10.0 (174 Reviews)
House
Oceanside home, dock,kayaks,bikes,pool,fishing,109
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $313
         

7.4 (552 Reviews)
Cabin
Sugarloaf Lodge
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $541
         

10.0 (155 Reviews)
House
Oceanside home, dock,kayaks,bikes,pool,fishing,111
  • Air Conditioner
  • Pool
  • TV

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Property Image From $583
         

New
House
Newly built home in Cudjoe Key
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $764
         

10.0 (39 Reviews)
House
Latitudes - Ocean front with salt water pool.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $196
         

10.0 (15 Reviews)
House
Getaway to the Quiet Florida Keys
  • Air Conditioner
  • Parking
  • TV

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

Weather in Upper Sugarloaf Key

View the weather forecast for Upper Sugarloaf Key before booking your Upper Sugarloaf Key Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Upper Sugarloaf Key, FL

Bigpineresortcottages offers a large selection of top attractions around Upper Sugarloaf Key. Research things to do on your vacation before you visit Upper Sugarloaf Key.


Florida Keys Beaches Saddlebunch Keys Looe Key National Marine Sanctuary Rockland Key Key West Fly Fishing Cook Island National Key Deer Refuge Visitor Center Key West Visitors Center No Name Key Blue Hole Shark Key Sugarloaf Beach Florida Keys Wilderness Boca Chica Nude Beach Big Pine Flea Market Upper Sugarloaf Sound Sheriff’s Animal Farm Lower Sugarloaf Sound Reel Deal Fishing Charters Perky’s Bat Tower