
Holiday rentals with a pool in Kailua
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Kailua
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Kailua rentals with a pool
House rentals with a pool

Waikiki Gem, Stunning Ocean View, Parking Included

Le'ale'a by AvantStay | Ocean + Mountain Views!

Kalo Homes ~ Mauka to Makai

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Family Oceanview Oasis, Hot Tub, 5min to beach

Support LOCAL - NEW! Mākaha Valley Home

Slice of Paradise-3BR- Sleeps10-same $ for 2 as 10

Sunny Heaven 1 Bd Plus Loft
Apartment rentals with a pool

Amazing Ocean & Beach Views - Only Steps to Beach!

🏝 Ilikai Condo Waikiki Beach Ocean Views

RusticLuxe — Go Fully Custom at Turtle Bay

Free Parking/Ocean View/Steps to Beach & Mall 33F

★Panoramic OCEAN VIEW Studio Suite + FREE Parking

43FL-Gorgeous High-FL Studio w/Ocean & City Views

Ocean View Studio | 2 Minute Walk to Waikiki Beach

Ko Olina Beach Villa Frontal Oceanview 2 bd/2 ba
Other holiday rentals with a pool

Ocean/Marina/Pool View 2BD Corner Unit AC @ Ilikai

Penthouse Upscale Oceanview King Studio Near Beach

Beautiful OceanView&Sunset @IlikaiResort w/Parking

New Listing! Stylish Waikiki Condo - Free Parking

29FL-Ultra Modern 1BR-Ocean View & Free Parking!

MOANA Ocean View Suite • High Floor • FREE Parking

Lux Panoramic Beach Views - Free Parking!

Ocean Front Luxurious Villa
Quick stats about holiday rentals with a pool in Kailua
Total rentals
90 properties
Nightly prices starting at
£52 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
70 properties are a good fit for families
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wifi availability
90 properties include access to wifi
Destinations to explore
- Honolulu Holiday rentals
- O‘ahu Holiday rentals
- Kauaʻi County Holiday rentals
- Island of Hawai'i Holiday rentals
- Waikiki Beach Holiday rentals
- Kailua-Kona Holiday rentals
- Kona Holiday rentals
- Kihei Holiday rentals
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- North Kona Holiday rentals
- Hilo Holiday rentals
- Princeville Holiday rentals
- Beachfront rentals Kailua
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- Rentals with a washing machine and dryer Kailua
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- Rentals with pools Honolulu County
- Rentals with pools Hawaii
- Rentals with pools United States
- Kailua Beach
- Waimea Bay Beach
- Ko Olina Resort
- Kepuhi Beach
- Lanikai Beach
- Kualoa Ranch
- Mālaekahana Beach
- Honolulu Zoo
- Mākoa Beach
- Banzai Pipeline
- Ala Moana Beach Park
- White Plains Beach
- Hanauma Bay
- Kalama Beach
- Kahala Hilton Beach
- Makao Beach
- Wet 'n' Wild Hawaii
- Diamond Head Beach Park
- Sans Souci Beach
- Pyramid Rock Beach
- Bishop Museum
- Nimitz Beach
- Ke Iki Beach
- Waimea Valley
- Things to do Kailua
- Things to do Honolulu County
- Food and drink Honolulu County
- Sports activities Honolulu County
- Art and culture Honolulu County
- Entertainment Honolulu County
- Nature and outdoors Honolulu County
- Wellness Honolulu County
- Things to do Hawaii
- Nature and outdoors Hawaii
- Art and culture Hawaii
- Entertainment Hawaii
- Food and drink Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Wellness Hawaii
- Tours Hawaii
- Things to do United States
- Food and drink United States
- Tours United States
- Sightseeing United States
- Entertainment United States
- Nature and outdoors United States
- Wellness United States
- Sports activities United States
- Art and culture United States