6082+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Lower Florida Keys pickleball Stays, Resort Rentals, & Homes

About Lower Florida Keys Vacation Rentals

Discover over 6082 amazing vacation rental options in Lower 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 Lower 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 780.24 ft², with prices averaging US $730 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 Lower Florida Keys.

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Top Pickleball-Ready Accommodation Types in Lower Florida Keys

Type Count
Vacation Homes 3496
Holiday Apartments 604
Cottages 189
Villas 62

Use these Quick Filters to Find a Vacation Rental in Lower 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 Lower Florida Keys with PickleTrip™.

Weather in Lower Florida Keys, FL

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

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


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
Key West Golf Club
Key West Lighthouse and Keeper's Quarters Museum
Ripley's Believe It or Not

Other Places to Stay in Lower Florida Keys, FL


Key West 3,088 Properties
Key West Historic District 2,409 Properties
Old Town 2,366 Properties
Duval Street 1,750 Properties
Downtown 992 Properties
Lower Keys 867 Properties
Uptown - Upper Duval 758 Properties
Historic Seaport 389 Properties
Cudjoe Key 384 Properties
Truman Annex 346 Properties
Big Pine Key 178 Properties
New Town 106 Properties

Frequently Asked Questions About Lower Florida Keys?

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

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

Discover 1117 accommodations with private or nearby pickleball courts in Lower Florida Keys. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Lower 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 Lower 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 6082 properties listed in Lower Florida Keys in 2026, 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 2409
Old Town Vacation Rentals in Florida 2366
Downtown Vacation Rentals in Florida 992
Uptown - Upper Duval Vacation Rentals in Florida 758
Historic Seaport Vacation Rentals in Florida 389
Truman Annex Vacation Rentals in Florida 346
New Town Vacation Rentals in Florida 106
Meadows Vacation Rentals in Florida 100
The Meadows Vacation Rentals in Florida 100
Cutthroat Harbor Estates Vacation Rentals in Florida 94
Bahama Village Vacation Rentals in Florida 93
Midtown Vacation Rentals in Florida 49
Port Pine Heights Vacation Rentals in Florida 112
Long Beach Estates Vacation Rentals in Florida 173
Doctor's Arm Vacation Rentals in Florida 281
Cudjoe Gardens Vacation Rentals in Florida 600

People Also Ask

There are 6082 Lower Florida Keys, FL Vacation Rentals

Recently Booked Vacation Rentals in Lower Florida Keys