Longboat Key pickleball Stays, Resort Rentals, & Homes
About Longboat Key Vacation Rentals
Discover over 849 amazing vacation rental options in Longboat 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 Longboat 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 852.27 ft², with prices averaging US $397 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 Longboat Key.
Top Pickleball-Ready Accommodation Types in Longboat Key
| Type | Count |
|---|---|
| Vacation Homes | 119 |
| Holiday Apartments | 79 |
| Villas | 7 |
| Cottages | 3 |
Use these Quick Filters to Find a Vacation Rental in Longboat 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 Longboat Key with PickleTrip™.
Weather in Longboat Key, FL
View the weather forecast for Longboat Key before booking your Longboat Key Vacation Rentals to confirm your best time to go.
Top Attractions Around Longboat Key, FL
PickleTrip offers a large selection of top attractions around Longboat Key . Research things to do on your vacation before you visit Longboat Key.
Other Places to Stay in Longboat Key, FL
Frequently Asked Questions About Longboat Key?
What are the top vacation rentals, resorts, and hotels in Longboat 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 Longboat 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 Longboat Key!
- 3 BEDROOM DIRECT OCEAN VIEW, WALKOUT TO THE BEACH!
- PENTHOUSE DOUBLE BALCONY FULL GULF & BAY VIEWS FROM EVERY ROOM Beachplace 5-602
- Gulf Front Luxury - "Serenity Sunset" - Long Boat Key, FL
- Gorgeous Gulf views and a beachfront location!
- REMODELED! Enjoy a Taste of Paradise from an Oceanfront Condo on White Sands!
- 3 BEDROOM PENTHOUSE "CRUISE SHIP" VIEWS w/DOUBLE BALCONY at Beachplace!
- Beach lovers dream
- Beachfront Longboat Key Condo 3BR Pool, Tennis & Private Beach Access
- Bayport Beach & Tennis Club ~ A Beach to Bay Tropical Oasis!
- Fantastic Beach Condo
How many pickleball-ready properties have private pools in Longboat Key?
Discover 94 accommodations with private or nearby pickleball courts in Longboat Key. Some of the best destinations to stay and play pickleball are:
- Gulf of Mexico Beach Front .Walk out condo steps from the private beach!
- LaPlaya 205D Spectacular sunsets and sunbathing from your private Gulf front lanai or sundeck
- Breathtaking Gulf Views Prestigious Long Boat Key
- Upscale Beachplace Condo.availability starting in May 2026.please inquire
Which vacation rentals, resorts, or hotels in Longboat Key is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Longboat 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.
- Gulf of Mexico Beach Front .Walk out condo steps from the private beach!
- Island Time Open Sun, July 19th!
- Casa Del Mar Longboat Key
How many PickleTrip vacation rentals or resorts are available in Longboat 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 849 properties listed in Longboat Key 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)
| Neighborhood | Property Count |
|---|---|
| Longbeach Village Vacation Rentals in Sarasota, Florida | 2398 |
| Bay Isles Vacation Rentals in Sarasota, Florida | 821 |
