217+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Jamaica
  2. Saint Elizabeth
  3. Southfield

Southfield pickleball Stays, Resort Rentals, & Homes

About Southfield Vacation Rentals

Discover over 217 amazing vacation rental options in Southfield 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 Southfield.

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 548.66 ft², with prices averaging $362 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 Southfield.

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Top Pickleball-Ready Accommodation Types in Southfield

Type Count
Villas 92
Vacation Homes 73
Holiday Apartments 25
Cottages 9

Use these Quick Filters to Find a Vacation Rental in Southfield

★ 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 Southfield with PickleTrip™.

Top Attractions Around Southfield, JM

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


Lovers Leap
Jamaica Beaches
Mega Mart
Billy Bay Beach
Northern Caribbean University
Floyd's Pelican Bar
Bubbling Spring Mineral Bath
Calabash Bay
Milk River Bath
Mandeville Hospital
Parrotee Pond Mangroves
Mandeville Parish Church
Marshall's Pen Great House
Cecil Charlton Park
Mandeville Market
Marshall’s Pen
Mrs Stephenson’s Garden
Manchester Parish Court
Callabash Bay Beach
High Street

Other Places to Stay in Southfield, JM


Lovers Leap 27 Properties

Frequently Asked Questions About Southfield?

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

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

Discover 39 accommodations with private or nearby pickleball courts in Southfield. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Southfield 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 Southfield?

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 217 properties listed in Southfield 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 217 Southfield, JM Vacation Rentals

Recently Booked Vacation Rentals in Southfield