451+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Kailua

Kailua pickleball Stays, Resort Rentals, & Homes

About Kailua Vacation Rentals

Discover over 451 amazing vacation rental options in Kailua 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 Kailua.

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 1354.79 ft², with prices averaging US $854 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 Kailua.

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Top Pickleball-Ready Accommodation Types in Kailua

Type Count
Vacation Homes 293
Holiday Apartments 93
Cottages 38
Villas 16

Use these Quick Filters to Find a Vacation Rental in Kailua

★ 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 Kailua with PickleTrip™.

Weather in Kailua, HI

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

December - February
High 79°F       Low 64°F
March - May
High 83°F       Low 66°F
June - August
High 84°F       Low 69°F
September - November
High 84°F       Low 66°F

Top Attractions Around Kailua, HI

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


Kailua Beach
Lanikai Beach
Kalama Beach Park
Kawainui Park
Royal Hawaiian Golf Club
Kailua Bay Beach
Mokapu Point
Kaneohe Klipper Golf Course
Lanikai Pillboxes Trailhead
Olomana Three Peaks Trail
Pohakupu
Ulu Po Heiau State Monument
Ala Moana Center
Diamond Head
Moana Surfrider
Royal Hawaiian Center
Honolulu Zoo
Honolulu Harbor
Waikiki Beach
Hanauma Bay Nature Preserve

Other Places to Stay in Kailua, HI


Ulu Po Heiau State Monument 433 Properties
Pohakupu 433 Properties
Kuulei Tract 432 Properties
Kailua Bay Beach 432 Properties
Kalama Beach Park 431 Properties
Kawainui Park 426 Properties
Enchanted Lake 411 Properties
Keolu Hills 396 Properties
Coconut Grove 314 Properties
Maunawili 301 Properties
Kalama Tract 147 Properties
Lanikai 79 Properties

Frequently Asked Questions About Kailua?

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

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

Discover 78 accommodations with private or nearby pickleball courts in Kailua. Some of the best destinations to stay and play pickleball are:

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

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

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 451 properties listed in Kailua 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 (7) 
Neighborhood Property Count
Kalama Tract Vacation Rentals in Kailua, Hawaii 147
Lanikai Vacation Rentals in Kailua, Hawaii 79
Coconut Grove Vacation Rentals in Kailua, Hawaii 314
Enchanted Lake Vacation Rentals in Kailua, Hawaii 411
Keolu Hills Vacation Rentals in Kailua, Hawaii 396
Kuulei Tract Vacation Rentals in Kailua, Hawaii 432
Palolo Vacation Rentals in Kailua, Hawaii 140

People Also Ask

There are 451 Kailua, HI Vacation Rentals

Recently Booked Vacation Rentals in Kailua