32+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Jamaica
  2. Westmoreland
  3. Caledonia

Caledonia pickleball Stays, Resort Rentals, & Homes

About Caledonia Vacation Rentals

Discover over 32 amazing vacation rental options in Caledonia 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 Caledonia.

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 239.22 ft², with prices averaging $473 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 Caledonia.

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Top Pickleball-Ready Accommodation Types in Caledonia

Type Count
Vacation Homes 15
Cottages 4
Villas 3
Holiday Apartments 2

Use these Quick Filters to Find a Vacation Rental in Caledonia

★ 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 Caledonia with PickleTrip™.

Top Attractions Around Caledonia, JM

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


Hip Strip
Doctor's Cave Beach
Montego Bay Cruise Ship Terminal
Montego Bay Marine Park
Jamaica Beaches
Tryall Golf Club
AquaSol Theme Park
Dead End Beach
Rocklands Bird Sanctuary
YS Falls
Sam Sharpe Square
Cornwall Regional Hospital
Mayfield Falls
Peter Tosh House
Saint James Parish Church
Walter Fletcher Beach
Bellefield Great House and Gardens
Jarret Park
Bluefields Beach
Westgate Shopping Centre

Frequently Asked Questions About Caledonia?

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

How many PickleTrip vacation rentals or resorts are available in Caledonia?

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 32 properties listed in Caledonia 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 32 Caledonia, JM Vacation Rentals

Recently Booked Vacation Rentals in Caledonia