1239+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Lower Keys pickleball Stays, Resort Rentals, & Homes

About Lower Keys Vacation Rentals

Discover over 1239 amazing vacation rental options in Lower 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 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 864.21 ft², with prices averaging US $409 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 Keys.

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Top Pickleball-Ready Accommodation Types in Lower Keys

Type Count
Vacation Homes 1055
Cottages 72
Holiday Apartments 14
Villas 12

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

Weather in Lower Keys, FL

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

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


Bahia Honda State Park and Beach
Florida Keys Beaches
Saddlebunch Keys
Looe Key National Marine Sanctuary
Rockland Key
Key West Fly Fishing
Upper Sugarloaf Key
Cook Island
National Key Deer Refuge Visitor Center
Key West Visitors Center
No Name Key
Calusa Beach
Blue Hole
Shark Key
Sugarloaf Beach
Florida Keys Wilderness
Boca Chica Nude Beach
Big Pine Flea Market
Upper Sugarloaf Sound
Loggerhead Beach

Other Places to Stay in Lower Keys, FL


Lower Florida Keys 3,804 Properties
Cudjoe Key 349 Properties
Big Pine Key 171 Properties
Cutthroat Harbor Estates 82 Properties
Little Torch Key 77 Properties
Sugarloaf Key 64 Properties
Summerland Key 61 Properties
Ramrod Key 45 Properties
Upper Sugarloaf Sound 38 Properties
Coupon Bight Aquatic Preserve 33 Properties
Breezeswept Beach Estates 30 Properties
Sugarloaf Shores 26 Properties

Frequently Asked Questions About Lower Keys?

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

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

Discover 280 accommodations with private or nearby pickleball courts in Lower Keys. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Lower 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 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 1239 properties listed in Lower 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
Cutthroat Harbor Estates Vacation Rentals in Florida 82
Breezeswept Beach Estates Vacation Rentals in Florida 30
Sugarloaf Shores Vacation Rentals in Florida 26
Eden Pines Vacation Rentals in Florida 404
Doctor's Arm Vacation Rentals in Florida 150
Port Pine Heights Vacation Rentals in Florida 98
Cudjoe Gardens Vacation Rentals in Florida 459
Sands Vacation Rentals in Florida 318
Long Beach Estates Vacation Rentals in Florida 154
Pine Channel Estates Vacation Rentals in Florida 415
Whispering Pines Vacation Rentals in Florida 334
Tropical Bay Estates Vacation Rentals in Florida 317
Geiger Key Vacation Rentals in Florida 35
Punta Brisa Vacation Rentals in Florida 260
Lambert Vacation Rentals in Florida 247
Atlantis Estates Vacation Rentals in Florida 325

People Also Ask

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