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Longwood pickleball Stays, Resort Rentals, & Homes

About Longwood Vacation Rentals

Discover over 67 amazing vacation rental options in Longwood 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 Longwood.

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 677.98 ft², with prices averaging US $304 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 Longwood.

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Top Pickleball-Ready Accommodation Types in Longwood

Type Count
Vacation Homes 52
Holiday Apartments 9
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Longwood

★ 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 Longwood with PickleTrip™.

Weather in Longwood, FL

View the weather forecast for Longwood before booking your Longwood 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 Longwood, FL

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


Boombah-Soldiers Creek Park
The Legacy at Alaqua Lakes
Rebounderz of Longwood
Big Tree Park
Aiguille Rock Climbing Center
The Trophy Club Of Orlando
Alaqua Country Club
Diamond Player's Club - Wekiva
SeaWorld® Orlando
Universal Orlando ResortTM
Universal Studios FloridaTM
Orange County Convention Center
Florida Mall
Orlando International Premium Outlets
Amway Center
Camping World Stadium
Holy Land Experience
The Wizarding World of Harry PotterTM
University of Central Florida
Aquatica

Other Places to Stay in Longwood, FL


North Orlando 545 Properties
Aiguille Rock Climbing Center 143 Properties
Rebounderz of Longwood 130 Properties
The Trophy Club Of Orlando 111 Properties
Big Tree Park 92 Properties
Boombah-Soldiers Creek Park 86 Properties
Diamond Player's Club - Wekiva 73 Properties
The Legacy at Alaqua Lakes 56 Properties
Wekiva Springs 38 Properties
Alaqua Country Club 38 Properties

Frequently Asked Questions About Longwood?

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

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

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

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 67 properties listed in Longwood 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.


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There are 67 Longwood, FL Vacation Rentals

Recently Booked Vacation Rentals in Longwood