97+ Vacation Rentals & Holiday Homes in Sugarloaf Key |
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Sugarloaf Key Accommodations - Hotels & Rentals

About Sugarloaf Key Vacation Rentals

Discover More than 97 Incredible Getaway Rentals Available in Sugarloaf Key. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Sugarloaf Key.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Sugarloaf Key, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Sugarloaf Key. The Average Size of Places to Stay Near Sugarloaf Key is 1139.78 ft², with Prices Averaging US $830 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Sugarloaf Key. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Sugarloaf Key

Type Count
Vacation Homes 85
Cottages 5
Holiday Apartments 2
Villas 1

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

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Sugarloaf Key with Online Reservations.

Weather in Sugarloaf Key, FL

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

Activities Sugarloaf KeyGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World Sugarloaf KeyGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Key West Fly Fishing
Upper Sugarloaf Key
Sugarloaf Beach
Upper Sugarloaf Sound
Duval Street
Smathers Beach
Southernmost Point
Mallory Square
South Beach
Higgs Beach
Bahia Honda State Park and Beach
Key West Harbour
Key West Aquarium
Ernest Hemingway Home and Museum
Fort Zachary Taylor Historic State Park
Key West Butterfly and Nature Conservatory
Florida Keys Beaches
Saddlebunch Keys
Harry S. Truman Little White House
Key West Shipwreck Museum

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Lower Florida Keys 3,972 Properties
Upper Sugarloaf Key 242 Properties
Key West Fly Fishing 128 Properties
Sugarloaf Beach 102 Properties
Upper Sugarloaf Sound 43 Properties
Sugarloaf Shores 25 Properties
Lower Sugarloaf Key 25 Properties

Frequently Asked Questions About Sugarloaf Key?

What are the top hotels, lake houses & vacation rentals in Sugarloaf Key?

We provide an array of great vacation destinations in Sugarloaf Key. If you are looking to stay in or around the Sugarloaf Key area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Sugarloaf Key:

How many Hotels & Vacation Rentals have private pools in Sugarloaf Key?

We have 11 Hotels & Vacation Rentals featuring a private pool in and near Sugarloaf Key. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Sugarloaf Key is best for families?

Searching for a family-friendly getaway in Sugarloaf Key? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Sugarloaf Key?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 97 in the Sugarloaf Key area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Sugarloaf Key.

Nearby Neighborhood (1) 
Neighborhood Property Count
Sugarloaf Shores Vacation Rentals in Sugarloaf Key, Florida 25

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