The Island pickleball Stays, Resort Rentals, & Homes

About The Island Vacation Rentals

Discover over 139 amazing vacation rental options in The Island 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 The Island.

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 1071.25 ft², with prices averaging US $477 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 The Island.

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Top Pickleball-Ready Accommodation Types in The Island

Type Count
Vacation Homes107
Holiday Apartments14
Villas4

Use these Quick Filters to Find a Vacation Rental in The Island

★ 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 The Island with PickleTrip™.

Weather in The Island, FL

View the weather forecast for The Island before booking your The Island 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

Frequently Asked Questions About The Island?

What are the top vacation rentals, resorts, and hotels in The Island 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 The Island. 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 The Island!

How many pickleball-ready properties have private pools in The Island?

Discover 18 accommodations with private or nearby pickleball courts in The Island. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in The Island? 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 The Island?

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 139 properties listed in The Island 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 (2) 

NeighborhoodProperty Count
North Palm Beach Heights Vacation Rentals in Florida 141
Abacoa Vacation Rentals in Florida 251

There are 139 The Island, FL Vacation Rentals

Recently Booked Vacation Rentals in The Island