
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, 18 reviews22% OFF! Lanikai Garden Studio - Since 1985!
Guest favourite

Apartment in Waikiki
5 out of 5 average rating, 39 reviewsPenthouse Upscale Oceanview King Studio Near Beach
Guest favourite

Shepherd’s hut in Kailua
5 out of 5 average rating, 7 reviewsThe Ohana Island Hut
Guest favourite

Condo in Waikiki
4.94 out of 5 average rating, 16 reviews*Renovated Cozy BOHO Studio - Waikiki Beach 3 mins
Guest favourite

Cottage in North Shore
4.87 out of 5 average rating, 127 reviewsBest Kept Secret on Oahu! and WE ARE LICENSED!!!

Apartment in Kailua
4.61 out of 5 average rating, 36 reviewsPeaceful 1 Bedroom/1 Bath Private Unit
Top Guest favourite

Home in Kahuku
4.95 out of 5 average rating, 42 reviewsOcean Pearl

Home in North Shore
4.8 out of 5 average rating, 290 reviewsHaleiwa Dream Location
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
- Kona Holiday rentals
- Kihei Holiday rentals
- Kaanapali Holiday rentals
- North Kona Holiday rentals
- Hilo Holiday rentals
- Princeville Holiday rentals
- Rentals with pools Kailua
- Rentals with outdoor seating Kailua
- Rentals with a kayak Kailua
- Pet-friendly rentals Kailua
- Rentals with an EV charger Kailua
- Rentals with beach access Kailua
- Condo rentals Kailua
- Villa rentals Kailua
- Apartment rentals Kailua
- Rentals with a hot tub Kailua
- Private suite rentals Kailua
- Rentals with a patio Kailua
- Beachfront rentals Kailua
- Family-friendly rentals Kailua
- Rentals with a washing machine and dryer Kailua
- House rentals Kailua
- Fitness-friendly rentals Kailua
- Waterfront rentals Kailua
- Beach condo rentals Kailua
- 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
- Sans Souci Beach
- Diamond Head Beach Park
- Wet 'n' Wild Hawaii
- Pyramid Rock Beach
- Bishop Museum
- Nimitz Beach
- Ke Iki Beach
- Waimea Valley
- Things to do Kailua
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- Art and culture Honolulu County
- Nature and outdoors Honolulu County
- Things to do Hawaii
- Art and culture Hawaii
- Tours Hawaii
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- Food and drink Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Entertainment Hawaii
- Wellness Hawaii
- Things to do United States
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