Charters By Owner - Vacation Rentals in Sugarloaf Shores

Private and Exclusive Florida Keys Getaway From US $995
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pelico Paradise From US $304
         

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9.6 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Private and Exclusive Beach Getaway From US $1,468
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Luxurious Oceanfront 5BR Property with heated Pool & Waterfall From US $779
         

The Villa of Pelico Palms From US $1,510
         

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

Luxury Places to Stay in Sugarloaf Shores

Over 134+ Luxury Places to Stay in or Near Sugarloaf Shores
Beach Front - Cassie`s Paradise Key West From US $5,539
         

9BR Estate | 3 Homes & Pool | 30 Min to KW From US $3,293
         

Villa of the Setting Sun From US $2,804
         

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8.0 (1 Review)
House
  • Air Conditioner
  • Pool
  • View
Private and Exclusive Beach Getaway From US $1,969
         

8.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Lighthouse - Beach Houses Key West From US $1,888
         

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

Top-Rated Vacation Rentals with a Pool in Sugarloaf Shores

Over 59+ Top-Rated Vacation Rentals with a Pool in or Near Sugarloaf Shores
Sugarloaf Key Hotel at KOA Resort From US $278
         

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9.8 (551 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Beautiful POOL3/2 Sleeps 8. ALL ROOMS Waterfront From US $610
         

Pet-Friendly Vacation Rentals in Sugarloaf Shores

Over 64+ Pet-Friendly Vacation Rentals in or Near Sugarloaf Shores
Sugarloaf Key RV Resort & Cottages From US $458
         

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9.1 (474 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Hemingway - Beach Houses Key West From US $1,218
         

9.6 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Beach Getaway in the Florida Keys From US $1,221
         

8.4 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Fish Camp | Old Florida canalfront getaway From US $159
         

8.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • TV

Large Vacation Homes & Villas in Sugarloaf Shores

Over 20+ Large Vacation Homes & Villas in or Near Sugarloaf Shores
Sugarloaf Lodge From US $189
         

7.4 (552 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pool
Stunning, Oceanfront Home with Private Pool & Docks - Dog-Friendly From US $225
         

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
         

Oceanfront Sugarloaf Key Home w/ Private Dock From US $254
         

Wheelchair Accessible Vacation Homes in Sugarloaf Shores

Over 2+ Wheelchair Accessible Vacation Homes in or Near Sugarloaf Shores
Coral Queen Palm From US $330
         

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New
House
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace
Sugarloaf Key Hotel at KOA Resort From US $150
         

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9.4 (42 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

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

Over 11+ Sugarloaf Shores Vacation Rentals and Airbnb Places to Stay Under $200
Sugar Loaf Lodge From US $190
         

8.2 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Our Happy Place From US $198
         

New
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Beautiful Waterfront Studio- Dock your boat here! - 15 mi to Key West. From US $150
         

Soothing cabin in Sugarloaf Key From US $177
         

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

Instantly Bookable Vacation Homes in Sugarloaf Shores

Over 41+ Instantly Bookable Vacation Homes in or Near Sugarloaf Shores
Waterfront, Pet Friendly - Loggerhead Lagoon From US $382
         

Into the Blues From US $371
         

New
House
  • Air Conditioner
  • Pet Friendly
  • TV

About Sugarloaf Shores Vacation Rentals

With more than 143 Sugarloaf Shores vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Chartersbyowner 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 Shores.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Chartersbyowner Sugarloaf Shores, 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 Shores. Places to stay near Sugarloaf Shores are 1171.02 ft² on average, with prices averaging $823 a night.

Chartersbyowner makes it easy and safe to find and compare vacation rentals in Sugarloaf Shores 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 Shores

Type Count
Vacation Homes 130
Cottages 5
Hotels with Suites 3
Cabin Rentals 2
Holiday Apartments 1
Villas 1

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

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

Weather in Sugarloaf Shores

View the weather forecast for Sugarloaf Shores before booking your Sugarloaf Shores 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 Shores Vacation Rental Frequently Asked Questions

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

Currently, the total number of properties listed in 2026 is over 143 in the Sugarloaf Shores area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Sugarloaf Shores.