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

Cruise And Resorts - Vacation Rentals in Upper Sugarloaf Key

Private Oceanfront Cottage with dockage, pool just minutes to Key West! From US $348
         

8.6 (165 Reviews)
Cottage
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pelico Paradise From US $304
         

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

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Atlantic View Luxury Villa with Pool From US $1,209
         

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

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Quaint cottage, pool, dockage just minutes to Key West! From US $441
         

9.0 (150 Reviews)
Cottage
Quaint cottage, pool, dockage just minutes to Key West!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury OceanView Friendly Villa Near Key West From US $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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Starlight Serenity - Hideaway w Stunning Views From US $770
         

New
House
Starlight Serenity - Hideaway w Stunning Views
  • Parking
  • Pet Friendly
  • Balcony/Terrace

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Cudjoe Cottages, swimming pool, just 20 miles from Key West From US $467
         

8.8 (150 Reviews)
House
Cudjoe Cottages, swimming pool, just 20 miles from Key West
  • Air Conditioner
  • Parking
  • Pet Friendly

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Red Grouper Getaway From US $311
         

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

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Sugarloaf Key Hotel at KOA Resort From US $278
         

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9.8 (478 Reviews)
Hotel
Sugarloaf Key Hotel at KOA Resort
  • Air Conditioner
  • Parking
  • Pool

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Charming cottages, dockage, pool, just minutes to Key West From US $413
         

8.6 (122 Reviews)
Cottage
Charming cottages, dockage, pool, just minutes to Key West
  • Air Conditioner
  • Parking
  • Pet Friendly

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

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Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5 From US $485
         

10.0 (228 Reviews)
House
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
  • Air Conditioner
  • Parking
  • Pool

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Oceanside home, dock,kayaks,bikes,pool,fishing,109 From US $525
         

10.0 (176 Reviews)
House
Oceanside home, dock,kayaks,bikes,pool,fishing,109
  • Air Conditioner
  • Parking
  • Pool

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Oceanside home, dock,kayaks,bikes,pool,fishing,111 From US $605
         

10.0 (158 Reviews)
House
Oceanside home, dock,kayaks,bikes,pool,fishing,111
  • Air Conditioner
  • Pool
  • TV

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Getaway to the Quiet Florida Keys From US $196
         

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

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Oceanfront Home With Large Private Deck with boat dockage From US $389
         

10.0 (11 Reviews)
House
Oceanfront Home With Large Private Deck with boat dockage
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West From US $390
         

10.0 (8 Reviews)
House
Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss! From US $291
         

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

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PARADISE on Sugarloaf Key! 704-650-8105 Summer and Fall low rates. From US $384
         

10.0 (6 Reviews)
House
PARADISE on Sugarloaf Key! 704-650-8105 Summer and Fall low rates.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Amazing waterfront home with private beach, dock, pool, WiFi & outdoor kitchen From US $456
         

10.0 (5 Reviews)
House
Amazing waterfront home with private beach, dock, pool, WiFi & outdoor kitchen
  • Air Conditioner
  • Parking
  • Pool

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Discounts are available for extended summer rentals. From US $458
         

10.0 (4 Reviews)
House
Discounts are available for extended summer rentals.
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Villa of Pelico Palms From US $1,780
         

10.0 (3 Reviews)
House
The Villa of Pelico Palms
  • Air Conditioner
  • Parking
  • Pool

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

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Magnificent Ocean views, privacy abounds on this well appointed mini estate. From US $542
         

10.0 (3 Reviews)
House
Magnificent Ocean views, privacy abounds on this well appointed mini estate.
  • Air Conditioner
  • Parking
  • Pet Friendly

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

Cruiseandresorts 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

Upper Sugarloaf Key Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Upper Sugarloaf Key?

Currently, the total number of properties listed in 2026 is over 237 in the Upper Sugarloaf Key area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Upper Sugarloaf Key.