525+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Florida
  3. Cudjoe Key

Cudjoe Key pickleball Stays, Resort Rentals, & Homes

About Cudjoe Key Vacation Rentals

Discover over 525 amazing vacation rental options in Cudjoe 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 Cudjoe 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 823.32 ft², with prices averaging US $356 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 Cudjoe Key.

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Top Pickleball-Ready Accommodation Types in Cudjoe Key

Type Count
Vacation Homes 406
Cottages 51
Villas 8
Holiday Apartments 2

Use these Quick Filters to Find a Vacation Rental in Cudjoe 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 Cudjoe Key with PickleTrip™.

Weather in Cudjoe Key, FL

View the weather forecast for Cudjoe Key before booking your Cudjoe Key Vacation Rentals to confirm your best time to go.

December - February
High 81°F       Low 67°F
March - May
High 87°F       Low 70°F
June - August
High 91°F       Low 80°F
September - November
High 90°F       Low 73°F

Top Attractions Around Cudjoe Key, FL

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


Smathers Beach
Higgs Beach
Bahia Honda State Park and Beach
Key West Harbour
Florida Keys Beaches
Saddlebunch Keys
Key West Golf Club
Key West Art and Historical Society
Robbie's
Fort East Martello Museum and Gallery
Studios of Key West
Looe Key National Marine Sanctuary
Rockland Key
Key West Fly Fishing
Upper Sugarloaf Key
Key West Tropical Forest and Botanical Garden
Cook Island
National Key Deer Refuge Visitor Center
Key West Visitors Center
Key West Garden Club

Other Places to Stay in Cudjoe Key, FL


Lower Keys 840 Properties
Cudjoe Gardens 459 Properties
Cutthroat Harbor Estates 84 Properties

Frequently Asked Questions About Cudjoe Key?

What are the top vacation rentals, resorts, and hotels in Cudjoe 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 Cudjoe 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 Cudjoe Key!

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

Discover 62 accommodations with private or nearby pickleball courts in Cudjoe Key. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Cudjoe 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 Cudjoe 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 525 properties listed in Cudjoe 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 (2) 
Neighborhood Property Count
Cutthroat Harbor Estates Vacation Rentals in Cudjoe Key, Florida 84
Cudjoe Gardens Vacation Rentals in Cudjoe Key, Florida 459

People Also Ask

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There are 525 Cudjoe Key, FL Vacation Rentals

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