Big Pine Resort Cottages - Vacation Rentals in Upper Sugarloaf Key

Private Oceanfront Cottage with dockage, pool just minutes to Key West! From US $375
         

Sugarloaf Key RV Resort & Cottages From US $458
         

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9.0 (371 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Quaint cottage, pool, dockage just minutes to Key West! From US $328
         

9.0 (147 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming cottages, dockage, pool, just minutes to Key West From US $413
         

8.6 (122 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Cottage with Pool and Dockage, just minutes to Key West From US $328
         

9.2 (162 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Cottage with swimming pool and dockage, just minutes to Key West! From US $239
         

9.0 (162 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Cottage with Pool and Boat Dockage just minutes to Key West! From US $214
         

8.6 (158 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
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

Upper Sugarloaf Key Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Upper Sugarloaf Key?
How many vacation rentals are available in Upper Sugarloaf Key?

Currently, the total number of properties listed in 2026 is over 18 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.