13487+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Florida Keys pickleball Stays, Resort Rentals, & Homes

About Florida Keys Vacation Rentals

Discover over 13487 amazing vacation rental options in Florida Keys 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 Florida Keys.

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 848.31 ft², with prices averaging US $617 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 Florida Keys.

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Top Pickleball-Ready Accommodation Types in Florida Keys

Type Count
Vacation Homes 8188
Holiday Apartments 1262
Villas 353
Cottages 273

Use these Quick Filters to Find a Vacation Rental in Florida Keys

★ 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 Florida Keys with PickleTrip™.

Weather in Florida Keys, FL

View the weather forecast for Florida Keys before booking your Florida Keys 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 Florida Keys, FL

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


Duval Street
Smathers Beach
Southernmost Point
Mallory Square
South Beach
Sombrero Beach
John Pennekamp Coral Reef State Park
Higgs Beach
Bahia Honda State Park and Beach
Key West Harbour
Key West Aquarium
Ernest Hemingway Home and Museum
Jimmy Johnson's Big Chill
Dolphin Research Center
Fort Zachary Taylor Historic State Park
Theater of the Sea
Key West Butterfly and Nature Conservatory
Florida Keys Beaches
Seven Mile Bridge
Saddlebunch Keys

Other Places to Stay in Florida Keys, FL


Lower Florida Keys 4,917 Properties
Key West 3,993 Properties
Key West Historic District 2,923 Properties
Old Town 2,836 Properties
Duval Street 2,154 Properties
Marathon 1,744 Properties
Pretty Joe Rock 1,610 Properties
Key Largo 1,610 Properties
Downtown 1,279 Properties
Lower Keys 974 Properties
Islamorada 938 Properties
Uptown - Upper Duval 875 Properties

Frequently Asked Questions About Florida Keys?

What are the top vacation rentals, resorts, and hotels in Florida Keys 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 Florida Keys. 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 Florida Keys!

How many pickleball-ready properties have private pools in Florida Keys?

Discover 2876 accommodations with private or nearby pickleball courts in Florida Keys. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Florida Keys? 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 Florida Keys?

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 13487 properties listed in Florida Keys 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 (16) 
Neighborhood Property Count
Key West Historic District Vacation Rentals in Florida 2923
Old Town Vacation Rentals in Florida 2836
Downtown Vacation Rentals in Florida 1279
Uptown - Upper Duval Vacation Rentals in Florida 875
Historic Seaport Vacation Rentals in Florida 467
Truman Annex Vacation Rentals in Florida 380
New Town Vacation Rentals in Florida 126
Bahama Village Vacation Rentals in Florida 107
Key Largo Village Vacation Rentals in Florida 52
Venetian Shores Vacation Rentals in Florida 46
Little Venice Vacation Rentals in Florida 44
Indigo Reef Marina Homes Vacation Rentals in Florida 42
Lower Matecumbe Beach Vacation Rentals in Florida 27
Coral Lagoon Vacation Rentals in Florida 1115
Pirates Cove Vacation Rentals in Florida 1222
White Marlin Beach Vacation Rentals in Florida 347

People Also Ask

There are 13487 Florida Keys, FL Vacation Rentals

Recently Booked Vacation Rentals in Florida Keys