
Vacation 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.
Vacation 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

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

Large family home 5 min from beach- with pool

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Makaha Hale - Serene 3 BR Home

Family Oceanview Oasis, Hot Tub, 5min to beach

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

Kalo Homes - Makaha's Hidden Gem

Oahu Perfect Vacation •Pool, Near Beach, Sleeps 14
Condo rentals with a pool

Gorgeous Boutique Studio in Central Waikiki~

Ocean View Studio | 2 Minute Walk to Waikiki Beach

NEW*STUNNING Luxury 1BR Ocean View*Central Waikiki

*Serendipity on the Moana! - Legal & Beachfront!*

#3103 Oceanfront 2BD/2BA apt | Free parking

Relaxing amazing Ocean and Diamond Head View

North Shore Oahu Getaway at Turtle Bay Resort

NEWLY RENOVATED (2021) Turtle Bay Haven!
Other vacation rentals with a pool

Peaceful cozy comfortable apartment

New Listing! Ocean & DiamondHead View/Free Parking

North Shore Turtle Bay Hideout

( Golden Week ) Nr beach! Imperial Resort

37FL-Luxury Upscale Ocean View-Modern 1BR/Parking~

Kuilima Estates West at Turtle Bay with King Bed

Ocean View Sunset, Free Parking, Pool, 5m to Beach

34FL-Upscale Mountain View 1BR-Waikiki w/Parking
Quick stats about vacation rentals with a pool in Kailua
Total rentals
90 properties
Nightly prices starting at
G$14,622 GYD 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 Vacation rentals
- O‘ahu Vacation rentals
- Kauaʻi County Vacation rentals
- Island of Hawai'i Vacation rentals
- Waikiki Beach Vacation rentals
- Kailua-Kona Vacation rentals
- Kihei Vacation rentals
- Kona Vacation rentals
- Kaanapali Vacation rentals
- Hilo Vacation rentals
- Princeville Vacation rentals
- North Kona Vacation rentals
- Rentals with a hot tub Kailua
- Condo rentals Kailua
- Beach condo rentals Kailua
- Private suite rentals Kailua
- Rentals with an EV charger Kailua
- Rentals with a kayak Kailua
- Rentals with a patio Kailua
- Rentals with beach access Kailua
- House rentals Kailua
- Rentals with outdoor seating Kailua
- Fitness-friendly rentals Kailua
- Waterfront rentals Kailua
- Apartment rentals Kailua
- Family-friendly rentals Kailua
- Pet-friendly rentals Kailua
- Beachfront rentals Kailua
- Villa rentals Kailua
- Guesthouse rentals Kailua
- Rentals with a washer and dryer Kailua
- Rentals with pools Honolulu County
- Rentals with pools Hawaii
- Rentals with pools United States
- Kailua Beach
- Waimea Bay Beach
- Ko Olina Resort
- Kualoa Ranch
- Lanikai Beach
- Kepuhi Beach
- Mālaekahana Beach
- Honolulu Zoo
- Banzai Pipeline
- Ala Moana Beach Park
- Mākoa Beach
- Hanauma Bay
- Kalama Beach
- White Plains Beach
- Kapiolani Park Beach
- Kahala Hilton Beach
- Sans Souci Beach
- Bishop Museum
- Diamond Head Beach Park
- Kalani Beach
- Nimitz Beach
- Pyramid Rock Beach
- Ke Iki Beach
- Wet 'n' Wild Hawaii
- Things to do Kailua
- Things to do Honolulu County
- Food and drink Honolulu County
- Sports activities Honolulu County
- Art and culture Honolulu County
- Tours Honolulu County
- Wellness Honolulu County
- Nature and outdoors Honolulu County
- Entertainment Honolulu County
- Things to do Hawaii
- Nature and outdoors Hawaii
- Food and drink Hawaii
- Entertainment Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Wellness Hawaii
- Art and culture Hawaii
- Tours Hawaii
- Things to do United States
- Food and drink United States
- Nature and outdoors United States
- Wellness United States
- Sports activities United States
- Art and culture United States
- Tours United States
- Sightseeing United States
- Entertainment United States