
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
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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, 16 reviewsLanikai Garden Studio - Licensed Since 1985!

Cottage in Kailua
4.88 out of 5 average rating, 41 reviewsKailua Ohana Cottage close to beach
Superhost

Flat in Waikiki
5 out of 5 average rating, 37 reviewsPenthouse Upscale Oceanview King Studio Near Beach
Superhost

Flat in Waikiki
5 out of 5 average rating, 10 reviewsOcean Breeze Retreat: Luxe High-Rise 21F
Superhost

Flat in Waikiki
4.95 out of 5 average rating, 41 reviewsThe Aloha Manor of Waikiki

Cottage in North Shore
4.87 out of 5 average rating, 124 reviewsBest Kept Secret on Oahu! and WE ARE LICENSED!!!

Home in Kaneohe
4.62 out of 5 average rating, 170 reviewsBeautiful Ocean view 2 bedroom rental (30 + days)

Apartment in Kahuku
5 out of 5 average rating, 12 reviewsThe Drifter - North Shore Loft - Relaxed Luxury
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
- Villa rentals Kailua
- Rentals with pools Kailua
- Rentals with a kayak Kailua
- Beach apartment rentals Kailua
- Beachfront rentals Kailua
- House rentals Kailua
- Pet-friendly rentals Kailua
- Family-friendly rentals Kailua
- Rentals with a patio Kailua
- Private suite rentals Kailua
- Family-friendly rentals Kailua
- Rentals with a washing machine and dryer Kailua
- Rentals with an EV charger Kailua
- Fitness-friendly rentals Kailua
- Waterfront rentals Kailua
- Flat rentals Kailua
- Rentals with outdoor seating Kailua
- Rentals with a hot tub Kailua
- Apartment rentals Kailua
- Rentals with beach access Kailua
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- Kailua Beach
- Waimea Bay Beach
- Ko Olina Resort
- Kepuhi Beach
- Lanikai Beach
- Mālaekahana Beach
- Kualoa Ranch
- Mākoa Beach
- Honolulu Zoo
- Banzai Pipeline
- Ala Moana Beach Park
- White Plains Beach
- Hanauma Bay
- Kaupoa Beach
- Makao Beach
- Diamond Head Beach Park
- Kalama Beach
- Sans Souci Beach
- Kahala Hilton Beach
- Nimitz Beach
- Bishop Museum
- Wet 'n' Wild Hawaii
- Pyramid Rock Beach
- Waimea Valley
- Things to do Kailua
- Things to do Honolulu County
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- Things to do United States
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