The Beaches Estates - Vacation Rentals in Sugarloaf Key

Pelico Paradise From US $304
         

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9.6 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Starlight Serenity - Hideaway w Stunning Views From US $727
         

10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Private and Exclusive Florida Keys Getaway From US $1,011
         

10.0 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Private and Exclusive Beach Getaway From US $1,446
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Villa of Pelico Palms From US $1,267
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Sugarloaf Key

Over 136+ Luxury Places to Stay in or Near Sugarloaf Key
Beach Front - Cassie`s Paradise Key West From US $5,627
         

The Hemingway - Beach Houses Key West From US $1,295
         

9.6 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Beach Getaway in the Florida Keys From US $1,163
         

8.4 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Sugarloaf Key

Over 68+ Top-Rated Vacation Rentals with a Pool in or Near Sugarloaf Key
Fisherman's Paradise From US $1,018
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Blue Wahoo-Perfect Keys Getaway From US $463
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sugarloaf Key Hotel at KOA Resort From US $278
         

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9.8 (591 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Sugarloaf Key

Over 65+ Pet-Friendly Vacation Rentals in or Near Sugarloaf Key
Starlight Serenity - Hideaway with Stunning Views From US $480
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury OceanView Friendly Villa Near Key West From US $804
         

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1.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
3-bedroom waterfront house in fabulous Cudjoe Key From US $358
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Private Secluded Ocean View & Pool Near Key West From US $712
         

8.0 (106 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Jekjak From US $820
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Pool

Large Vacation Homes & Villas in Sugarloaf Key

Over 21+ Large Vacation Homes & Villas in or Near Sugarloaf Key
Sugarloaf Key RV Resort & Cottages From US $458
         

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9.1 (550 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa and Guest House of Pelico Palms From US $1,757
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool
Ocean9 Villa, amazing waterfront, 15 min away from Duval Street! From US $1,043
         

Florida Keys Beach Getaway From US $1,811
         

9.8 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Sugarloaf Key

Over 3+ Wheelchair Accessible Vacation Homes in or Near Sugarloaf Key
Sugarloaf Lodge From US $126
         

7.7 (420 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pool
Sugarloaf Key Hotel at KOA Resort From US $150
         

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9.4 (380 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Sugarloaf Key Vacation Rentals and Airbnb Places to Stay Under $200

Over 9+ Sugarloaf Key Vacation Rentals and Airbnb Places to Stay Under $200
Getaway to the Quiet Florida Keys From US $178
         

10.0 (17 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Sugar Loaf Lodge From US $190
         

8.2 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Soothing cabin in Sugarloaf Key From US $177
         

New
Cabin
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Sugarloaf Key

Over 47+ Instantly Bookable Vacation Homes in or Near Sugarloaf Key
The Lighthouse - Beach Houses Key West From US $1,012
         

9.6 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Sugarloaf Key Vacation Rentals

With more than 145 Sugarloaf Key vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Thebeachestates and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Sugarloaf Key.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Thebeachestates Sugarloaf Key, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Sugarloaf Key. Places to stay near Sugarloaf Key are 1162.26 ft² on average, with prices averaging US $700 a night.

Thebeachestates makes it easy and safe to find and compare vacation rentals in Sugarloaf Key with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Sugarloaf Key

Type Count
Vacation Homes 132
Cottages 5
Hotels 3
Cabin Rentals 2
Villas 2

Use these Quick Filters to Find a Vacation Rental in Sugarloaf Key

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

Weather in Sugarloaf Key

View the weather forecast for Sugarloaf Key before booking your 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

Sugarloaf Key Vacation Rental Frequently Asked Questions

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

Currently, the total number of properties listed in 2026 is over 145 in the Sugarloaf Key area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Sugarloaf Key.