
Holiday rentals 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
Get the amount of space that is right for you
Popular amenities for Kailua holiday rentals
Other great holiday rentals in Kailua
Guest favourite

Apartment in Waianae
5 out of 5 average rating, 51 reviewsBeach Front, King Bed, the Princess - low level
Guest favourite

Home in Waianae
4.98 out of 5 average rating, 80 reviewsMakaha Hale - New 3 BR Home
Top guest favourite

Apartment in Waikiki
5 out of 5 average rating, 19 reviewsMOANA Ocean View Suite • 31st Floor • FREE Parking
Guest favourite

Flat in Kahuku
5 out of 5 average rating, 46 reviewsNorth Shore Turtle Bay Hideout
Top guest favourite

Home in Makaha Valley
5 out of 5 average rating, 34 reviewsKalo Homes - Breath of Life
Top guest favourite

Apartment in Waikiki
5 out of 5 average rating, 68 reviews*RARE* Nami 1BR SUITE | Luxurious Ocean View
Superhost

Apartment in Waianae
4.91 out of 5 average rating, 90 reviewsLuxury Ocean Front W/Private Beach, Pool, & HotTub

Home in Kailua
4.83 out of 5 average rating, 140 reviewsSerenity Beachfront Cottage- NUC No 90/TVU-0326
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
- Villa rentals Kailua
- Fitness-friendly rentals Kailua
- Waterfront rentals Kailua
- Rentals with a washing machine and dryer Kailua
- Rentals with pools Kailua
- Rentals with a kayak Kailua
- Rentals with outdoor seating Kailua
- Rentals with a hot tub Kailua
- Beachfront rentals Kailua
- Rentals with an EV charger Kailua
- Family-friendly rentals Kailua
- Pet-friendly rentals Kailua
- Apartment rentals Kailua
- Flat rentals Kailua
- Beach apartment rentals Kailua
- Rentals with beach access Kailua
- House rentals Kailua
- Private suite rentals Kailua
- Rentals with a patio 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
- Hanauma Bay
- Kalama Beach
- White Plains Beach
- Kapiolani Park Beach
- Sans Souci Beach
- Kahala Hilton Beach
- Bishop Museum
- Diamond Head Beach Park
- Nimitz Beach
- Pyramid Rock Beach
- Kalani Beach
- Ke Iki Beach
- Wet 'n' Wild Hawaii
- Things to do Kailua
- Things to do Honolulu County
- Entertainment Honolulu County
- Art and culture Honolulu County
- Food and drink Honolulu County
- Sports activities Honolulu County
- Wellness Honolulu County
- Nature and outdoors Honolulu County
- Things to do Hawaii
- Nature and outdoors Hawaii
- Tours Hawaii
- Entertainment Hawaii
- Wellness Hawaii
- Food and drink Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Art and culture Hawaii
- Things to do United States
- Sports activities United States
- Nature and outdoors United States
- Sightseeing United States
- Art and culture United States
- Food and drink United States
- Entertainment United States
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- Wellness United States