Jamaica pickleball Stays, Resort Rentals, & Homes
About Jamaica Vacation Rentals
Discover over 26 amazing vacation rental options in Jamaica 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 Jamaica.
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 1222.43 ft², with prices averaging US $417 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 Jamaica.
Top Pickleball-Ready Accommodation Types in Jamaica
| Type | Count |
|---|---|
| Vacation Homes | 18 |
| Cottages | 6 |
| Holiday Apartments | 1 |
Use these Quick Filters to Find a Vacation Rental in Jamaica
★ 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 Jamaica with PickleTrip™.
Weather in Jamaica, VA
View the weather forecast for Jamaica before booking your Jamaica Vacation Rentals to confirm your best time to go.
Top Attractions Around Jamaica, VA
PickleTrip offers a large selection of top attractions around Jamaica . Research things to do on your vacation before you visit Jamaica.
Other Places to Stay in Jamaica, VA
Frequently Asked Questions About Jamaica?
What are the top vacation rentals, resorts, and hotels in Jamaica 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 Jamaica. 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 Jamaica!
- Little White Rose Cottage on the banks of the Rappahannock River
- Hot Tub + Private Beach: Waterfront Urbanna Escape
- Urbanna Cottage w/Private Yard & Water Views
- Waterfront Urbanna Home w/Private Dock & Pool
- Newly renovated cottage on the Rappahannock!
- Waterfront retreat w/pool, dock & fire pit in Urbanna. BRING YOUR BOAT!
- Waterfront Urbanna Home with Private Dock and Pool
- Bethpage Hewick Two-Bedroom Cottage 26
- Urbanna Cottage with Private Yard and Water Views
- Fish On-Site: Rappahannock River Gem!
How many PickleTrip vacation rentals or resorts are available in Jamaica?
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 26 properties listed in Jamaica 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.
