Winter Haven pickleball Stays, Resort Rentals, & Homes
About Winter Haven Vacation Rentals
Discover over 391 amazing vacation rental options in Winter Haven 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 Winter Haven.
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 915.69 ft², with prices averaging US $286 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 Winter Haven.
Top Pickleball-Ready Accommodation Types in Winter Haven
| Type | Count |
|---|---|
| Vacation Homes | 268 |
| Holiday Apartments | 51 |
| Cottages | 10 |
| Villas | 7 |
Use these Quick Filters to Find a Vacation Rental in Winter Haven
★ 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 Winter Haven with PickleTrip™.
Weather in Winter Haven, FL
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Top Attractions Around Winter Haven, FL
PickleTrip offers a large selection of top attractions around Winter Haven . Research things to do on your vacation before you visit Winter Haven.
Other Places to Stay in Winter Haven, FL
Frequently Asked Questions About Winter Haven?
What are the top vacation rentals, resorts, and hotels in Winter Haven 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 Winter Haven. 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 Winter Haven!
- Disney and Universal Studios only 30 minutes away
- Ricks's Retreat - Downtown Winter Haven Getaway, Near Chain of Lakes
- Private pool lake house with game room—just 4 minutes from LEGOLAND
- Waterfront Winter Haven Home with Dock & Hot Tub!
- Winter Haven, FL Pet Friendly Residential Retreat
- Waterfront Lakehouse, Private Dock, Tiki Bar, Playground, Near Legoland | Lake Idylwild Delight
- Lake Rochelle Rental Lakefront
- Hot Tub & Fire Pit: Lakefront Home on Lake Eloise
- Spectacular Waterfront Home in Winter Haven
- Fantastic Water Front Home on the Chain of Lakes
How many pickleball-ready properties have private pools in Winter Haven?
Discover 37 accommodations with private or nearby pickleball courts in Winter Haven. Some of the best destinations to stay and play pickleball are:
- Lake Shipp House with pool and dock on the water
- The Russell Lake House
- Heated Pool, Arcade with PS5, 5min from Legoland-Stylish LakeHome
- Newly remodeled Vacation Home with Saltwater Pool
Which vacation rentals, resorts, or hotels in Winter Haven is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Winter Haven? 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.
- 1-bedroom Apartment C near Hospitals/Legoland/Chain of Lakes
- BlockHaven near Legoland, Disney
- BlockHaven near Legoland & Disney
How many PickleTrip vacation rentals or resorts are available in Winter Haven?
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 391 properties listed in Winter Haven 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 (1)
| Neighborhood | Property Count |
|---|---|
| Winterset Gardens Vacation Rentals in Winter Haven, Florida | 149 |
