696+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Jamaica
  2. Saint Mary
  3. Castleton

Castleton pickleball Stays, Resort Rentals, & Homes

About Castleton Vacation Rentals

Discover over 696 amazing vacation rental options in Castleton 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 Castleton.

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 914.54 ft², with prices averaging US $286 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 Castleton.

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Top Pickleball-Ready Accommodation Types in Castleton

Type Count
Holiday Apartments 383
Vacation Homes 189
Villas 28
Cottages 13

Use these Quick Filters to Find a Vacation Rental in Castleton

★ 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 Castleton with PickleTrip™.

Weather in Castleton, JM

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

December - February
High 88°F       Low 73°F
March - May
High 89°F       Low 75°F
June - August
High 92°F       Low 75°F
September - November
High 90°F       Low 75°F

Top Attractions Around Castleton, JM

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


Castleton Gardens
James Bond Beach
Bob Marley Museum
Jamaica Beaches
Emancipation Park
Devon House
Blue and John Crow Mountains National Park
University of the West Indies
Jamaica House
USA Embassy
Jamaica Conference Center
National Gallery of Jamaica
National Stadium
Kingston and St. Andrew Parish Library
Cool Blue Hole
National Heroes Park
Mahoe Bay
Manor Park Plaza
Rio Nuevo Battle Site
Somerset Falls

Other Places to Stay in Castleton, JM


Castleton Gardens 699 Properties

Frequently Asked Questions About Castleton?

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

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

Discover 21 accommodations with private or nearby pickleball courts in Castleton. Some of the best destinations to stay and play pickleball are:

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

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

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 696 properties listed in Castleton 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 696 Castleton, JM Vacation Rentals

Recently Booked Vacation Rentals in Castleton