184+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Cayman Islands
  2. George Town

George Town pickleball Stays, Resort Rentals, & Homes

About George Town Vacation Rentals

Discover over 184 amazing vacation rental options in George Town 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 George Town.

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 1634.11 ft², with prices averaging US $1,048 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 George Town.

Show more
Show less

Top Pickleball-Ready Accommodation Types in George Town

Type Count
Vacation Homes 67
Holiday Apartments 46
Villas 20
Cottages 1

Use these Quick Filters to Find a Vacation Rental in George Town

★ 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 George Town with PickleTrip™.

Weather in George Town, KY

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

December - February
High 86°F       Low 72°F
March - May
High 89°F       Low 73°F
June - August
High 92°F       Low 76°F
September - November
High 91°F       Low 74°F

Top Attractions Around George Town, KY

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


Port of Georgetown
Cayman Islands National Museum
Cayman Maritime Treasure Museum
St. Ignatius Catholic Church
LCM David Nicholson Shipwreck
National Trust for the Cayman Islands
Georgetown Museum
Peace Memorial and Clock Tower
Governor Michael Gore Bird Sanctuary
Pure Art Gallery
Pedro St. James National Historic Site
Fort George
Spotts Beach
Grand Cayman Blow Holes
Camana Bay
Stingray City
Cayman Turtle Farm
Tiki Beach
Governor's Beach
Grand Cayman Beaches

Other Places to Stay in George Town, KY


Cayman Maritime Treasure Museum 871 Properties
Peace Memorial and Clock Tower 790 Properties
Port of Georgetown 789 Properties
Fort George 787 Properties
Georgetown Museum 785 Properties
Grand Harbour 112 Properties
Bonnie View Estates 89 Properties
Patricks Island 88 Properties
North Sound Estates 59 Properties
Newlands 32 Properties
Savannah 32 Properties
South Sound 25 Properties

Frequently Asked Questions About George Town?

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

How many pickleball-ready properties have private pools in George Town?

Discover 12 accommodations with private or nearby pickleball courts in George Town. Some of the best destinations to stay and play pickleball are:

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

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

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 184 properties listed in George Town 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.

Nearby Neighborhood (1) 
Neighborhood Property Count
South Sound Vacation Rentals in George Town 25

People Also Ask

There are 184 George Town, KY Vacation Rentals

Recently Booked Vacation Rentals in George Town