42+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Cayman Islands
  2. Old Man Bay

Old Man Bay pickleball Stays, Resort Rentals, & Homes

About Old Man Bay Vacation Rentals

Discover over 42 amazing vacation rental options in Old Man Bay 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 Old Man Bay.

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 1635.97 ft², with prices averaging US $623 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 Old Man Bay.

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Top Pickleball-Ready Accommodation Types in Old Man Bay

Type Count
Vacation Homes 24
Holiday Apartments 3
Villas 2
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Old Man Bay

★ 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 Old Man Bay with PickleTrip™.

Top Attractions Around Old Man Bay, KY

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


Grand Cayman Blow Holes
Port of Georgetown
Camana Bay
Stingray City
Cayman Turtle Farm
Tiki Beach
Governor's Beach
Grand Cayman Beaches
Cemetery Beach
Starfish Beach
North Sound
Cayman Islands National Museum
The Strand Shopping Center
Cayman Maritime Treasure Museum
Dolphin Cove
Kittiwake Shipwreck and Artificial Reef
North Wall
Hell
Star Fish Point
Rum Point Beach

Frequently Asked Questions About Old Man Bay?

What are the top vacation rentals, resorts, and hotels in Old Man Bay 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 Old Man Bay. 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 Old Man Bay!

How many pickleball-ready properties have private pools in Old Man Bay?

Discover 1 accommodations with private or nearby pickleball courts in Old Man Bay. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Old Man Bay? 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 Old Man Bay?

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 42 properties listed in Old Man Bay 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 42 Old Man Bay, KY Vacation Rentals

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