525+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Cayman Islands
  2. North Side

North Side pickleball Stays, Resort Rentals, & Homes

About North Side Vacation Rentals

Discover over 525 amazing vacation rental options in North Side 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 North Side.

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 1530.98 ft², with prices averaging US $1,133 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 North Side.

Show more
Show less

Top Pickleball-Ready Accommodation Types in North Side

Type Count
Vacation Homes 253
Holiday Apartments 65
Villas 53
Cottages 6

Use these Quick Filters to Find a Vacation Rental in North Side

★ 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 North Side with PickleTrip™.

Top Attractions Around North Side, KY

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


Starfish Beach
Star Fish Point
Rum Point Beach
Babylon
Cayman Kai Public Beach
Mastic Trail North Trailhead
Queen Elizabeth II Botanic Park
Mastic Trail South Trailhead
Grand Cayman Blow Holes
Port of Georgetown
Camana Bay
Stingray City
Cayman Turtle Farm
Tiki Beach
Governor's Beach
Grand Cayman Beaches
Cemetery Beach
North Sound
Cayman Islands National Museum
The Strand Shopping Center

Other Places to Stay in North Side, KY


Cayman Kai Public Beach 401 Properties
Rum Point Beach 400 Properties
Star Fish Point 400 Properties
Starfish Beach 398 Properties
Rum Point 263 Properties
Mastic Trail South Trailhead 143 Properties
Mastic Trail North Trailhead 135 Properties
Breakers 124 Properties
Queen Elizabeth II Botanic Park 117 Properties
Brinkleys 115 Properties
Babylon (Dive Site) 107 Properties
Old Man Bay 39 Properties

Frequently Asked Questions About North Side?

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

How many pickleball-ready properties have private pools in North Side?

Discover 145 accommodations with private or nearby pickleball courts in North Side. Some of the best destinations to stay and play pickleball are:

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

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

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 525 properties listed in North Side in 2026, 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 525 North Side, KY Vacation Rentals

Recently Booked Vacation Rentals in North Side