78+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Port Richey
  4. Pine Island

Pine Island pickleball Stays, Resort Rentals, & Homes

About Pine Island Vacation Rentals

Discover over 78 amazing vacation rental options in Pine 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 Pine 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 779.56 ft², with prices averaging US $278 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 Pine Island.

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Top Pickleball-Ready Accommodation Types in Pine Island

Type Count
Vacation Homes 66
Holiday Apartments 5
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Pine 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 Pine Island with PickleTrip™.

Weather in Pine Island, FL

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

December - February
High 75°F       Low 47°F
March - May
High 86°F       Low 49°F
June - August
High 91°F       Low 70°F
September - November
High 89°F       Low 53°F

Top Attractions Around Pine Island, FL

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


Pine Island Beach Park
Weeki Wachee Springs
Hudson Beach
Homosassa Springs Wildlife State Park
World Woods Golf Club
Bayport Park Boat Ramp
Werner Boyce Salt Springs State Park
Sand Key
Brooksville Country Club
Weeki Wachee River
Colorama Music
Show Palace Dinner Theater
Bird Island
Summertree Golf Course
Strong Tower Vineyard
Silverthorn Country Club
Homosassa Butterfly
HerNonedo Oaks Golf and Country Club
Nature Coast Botanical Gardens
Chassahowitzka Wildlife Reserve

Other Places to Stay in Pine Island, FL


Pine Island Beach Park 110 Properties

Frequently Asked Questions About Pine Island?

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

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

Looking for a fun and active getaway with pickleball courts in Pine 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 Pine 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 78 properties listed in Pine Island 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.


People Also Ask

There are 78 Pine Island, FL Vacation Rentals

Recently Booked Vacation Rentals in Pine Island