63+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Greenwood pickleball Stays, Resort Rentals, & Homes

About Greenwood Vacation Rentals

Discover over 63 amazing vacation rental options in Greenwood 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 Greenwood.

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 2104.45 ft², with prices averaging US $263 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 Greenwood.

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Top Pickleball-Ready Accommodation Types in Greenwood

Type Count
Vacation Homes 26
Holiday Apartments 13
Villas 11
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Greenwood

★ 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 Greenwood with PickleTrip™.

Top Attractions Around Greenwood, JM

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


Greenwood Great House
Hip Strip
Rose Hall Great House
Doctor's Cave Beach
Montego Bay Cruise Ship Terminal
Montego Bay Marine Park
Jamaica Beaches
Luminous Lagoon
AquaSol Theme Park
Half Moon Golf Course
Montego Bay Convention Centre
Dead End Beach
Rocklands Bird Sanctuary
Sam Sharpe Square
Martha Brae River
Cornwall Regional Hospital
Cinnamon Hill Golf Course
Saint James Parish Church
Jamaica Swamp Safari Village

Other Places to Stay in Greenwood, JM


Greenwood Great House 55 Properties

Frequently Asked Questions About Greenwood?

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

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

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

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 63 properties listed in Greenwood 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.


People Also Ask

There are 63 Greenwood, JM Vacation Rentals

Recently Booked Vacation Rentals in Greenwood