101+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Florida
  3. Sugarloaf Key

Sugarloaf Key pickleball Stays, Resort Rentals, & Homes

About Sugarloaf Key Vacation Rentals

Discover over 101 amazing vacation rental options in Sugarloaf Key with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Sugarloaf Key.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 1128.74 ft², with prices averaging US $870 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Sugarloaf Key.

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Top Pickleball-Ready Accommodation Types in Sugarloaf Key

Type Count
Vacation Homes 89
Cottages 5
Villas 1

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

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Sugarloaf Key with PickleTrip™.

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

Top Attractions Around Sugarloaf Key, FL

PickleTrip offers a large selection of top attractions around Sugarloaf Key . Research things to do on your vacation before you visit Sugarloaf Key.


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

Other Places to Stay in Sugarloaf Key, FL


Lower Florida Keys 4,807 Properties
Upper Sugarloaf Key 242 Properties
Key West Fly Fishing 128 Properties
Sugarloaf Beach 102 Properties
Upper Sugarloaf Sound 54 Properties
Sugarloaf Shores 27 Properties
Lower Sugarloaf Key 27 Properties

Frequently Asked Questions About Sugarloaf Key?

What are the top vacation rentals, resorts, and hotels in Sugarloaf Key with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Sugarloaf Key. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Sugarloaf Key!

How many pickleball-ready properties have private pools in Sugarloaf Key?

Discover 13 accommodations with private or nearby pickleball courts in Sugarloaf Key. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Sugarloaf Key is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Sugarloaf Key? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

How many PickleTrip vacation rentals or resorts are available in Sugarloaf Key?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 101 properties listed in Sugarloaf Key in 2025, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.

Nearby Neighborhood (1) 
Neighborhood Property Count
Sugarloaf Shores Vacation Rentals in Sugarloaf Key, Florida 27

People Also Ask

There are 101 Sugarloaf Key, FL Vacation Rentals

Recently Booked Vacation Rentals in Sugarloaf Key