
Holiday houses in Kailua
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Top-rated holiday rentals in Kailua
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Kailua holiday rentals
Other great holiday rentals in Kailua

Guest suite in Kailua
5 out of 5 average rating, 19 reviewsLicensed Lanikai Garden Studio - Since 1985!
Superhost

Apartment in Waikiki
5 out of 5 average rating, 34 reviewsThe Ocean Luxe in Waikiki, 1 Parking
Superhost

Condo in Waikiki
5 out of 5 average rating, 20 reviewsMOANA Ocean View Suite • 31st Floor • FREE Parking
Superhost

Condo in Waikiki
4.94 out of 5 average rating, 54 reviewsLuxury Oceanfront Waikiki Beach Tower w Ocean View

Cottage in North Shore
4.88 out of 5 average rating, 130 reviewsBest Kept Secret on Oahu! and WE ARE LICENSED!!!
Superhost

Tiny home in Hauula
4.79 out of 5 average rating, 14 reviewsCountryside Getaway

Condo in Kahuku
4.97 out of 5 average rating, 167 reviewsHonu Hideout at Turtle Bay
Superhost

Townhouse in North Shore
4.96 out of 5 average rating, 25 reviewsSunset Hale
Quick stats about holiday rentals in Kailua
Total rentals
360 properties
Total number of reviews
11K reviews
Family-friendly rentals
210 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
90 properties have a pool
Rentals with dedicated workspaces
180 properties have a dedicated workspace
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
- Kihei Holiday rentals
- Kona Holiday rentals
- Kaanapali Holiday rentals
- North Kona Holiday rentals
- Princeville Holiday rentals
- Hilo Holiday rentals
- Rentals with pools Kailua
- Beachfront rentals Kailua
- Family-friendly rentals Kailua
- Rentals with a patio Kailua
- Beach condo rentals Kailua
- Private suite rentals Kailua
- Rentals with a hot tub Kailua
- Condo rentals Kailua
- Villa rentals Kailua
- Rentals with an EV charger Kailua
- House rentals Kailua
- Guesthouse rentals Kailua
- Fitness-friendly rentals Kailua
- Waterfront rentals Kailua
- Apartment rentals Kailua
- Pet-friendly rentals Kailua
- Rentals with a washing machine and dryer Kailua
- Rentals with beach access Kailua
- Rentals with outdoor seating Kailua
- Rentals with a kayak Kailua
- Kailua Beach
- Waimea Bay Beach
- Ko Olina Resort
- Kualoa Ranch
- Lanikai Beach
- Kepuhi Beach
- Mālaekahana Beach
- Honolulu Zoo
- Banzai Pipeline
- Mākoa Beach
- Ala Moana Beach Park
- Kalama Beach
- Hanauma Bay
- White Plains Beach
- Kapiolani Park Beach
- Sans Souci Beach
- Kahala Hilton Beach
- Bishop Museum
- Diamond Head Beach Park
- Nimitz Beach
- Ke Iki Beach
- Pyramid Rock Beach
- Kalani Beach
- Wet 'n' Wild Hawaii
- Things to do Kailua
- Things to do Honolulu County
- Entertainment Honolulu County
- Wellness Honolulu County
- Sports activities Honolulu County
- Nature and outdoors Honolulu County
- Food and drink Honolulu County
- Art and culture Honolulu County
- Things to do Hawaii
- Nature and outdoors Hawaii
- Art and culture Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Wellness Hawaii
- Tours Hawaii
- Entertainment Hawaii
- Food and drink Hawaii
- Things to do United States
- Tours United States
- Sports activities United States
- Entertainment United States
- Nature and outdoors United States
- Wellness United States
- Food and drink United States
- Sightseeing United States
- Art and culture United States