10420+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Jamaica

Jamaica pickleball Stays, Resort Rentals, & Homes

About Jamaica Vacation Rentals

Discover over 10420 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 961.02 ft², with prices averaging US $459 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.

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Top Pickleball-Ready Accommodation Types in Jamaica

Type Count
Holiday Apartments 3497
Vacation Homes 3415
Villas 2122
Cottages 136

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

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

December - February
High 88°F       Low 73°F
March - May
High 89°F       Low 74°F
June - August
High 92°F       Low 78°F
September - November
High 91°F       Low 75°F

Top Attractions Around Jamaica

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


Seven Mile Beach
Dunn's River Falls
Hip Strip
Rose Hall Great House
Doctor's Cave Beach
Montego Bay Cruise Ship Terminal
Dolphin Cove
Turtle Beach
James Bond Beach
Bob Marley Museum
Negril Cliffs
Montego Bay Marine Park
Bloody Bay Beach
Mystic Mountain
Negril Lighthouse
Jamaica Beaches
Green Grotto Caves
Bloody Bay
Emancipation Park
Tryall Golf Club
Luminous Lagoon
AquaSol Theme Park
Blue Lagoon
Hellshire Beach
Devon House
Half Moon Golf Course
Montego Bay Convention Centre
Mahogany Beach
Dead End Beach
Turtle River Park

Other Places to Stay in Jamaica


North Coast 4,594 Properties
Montego Bay 4,044 Properties
Middlesex County 3,167 Properties
Cornwall County 2,899 Properties
Surrey County 1,836 Properties
Saint Ann 1,715 Properties
Kingston 1,625 Properties
Saint James 1,561 Properties
Ocho Rios 1,444 Properties
Saint Andrew 1,164 Properties
Ocho Rios 933 Properties
Westmoreland 692 Properties

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!

How many pickleball-ready properties have private pools in Jamaica?

Discover 1259 accommodations with private or nearby pickleball courts in Jamaica. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Jamaica? 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 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 10420 properties listed in Jamaica 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.


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There are 10420 Jamaica Vacation Rentals

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