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Cottage vacation rentals in Kailua

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Kailua

Guests agree: these cottages are highly rated for location, cleanliness, and more.

Guest favorite
Cottage in Kailua
The Windsurfer Cottage- by Kailua Beach
The brand new Windsurfer Cottage is a stand alone and private cottage located 100 yards from beautiful Kailua Beach on the windward side of Oahu. Construction completed November 2017. It is landscaped in true Hawaiiana-style. Palm trees, plumeria trees, breadfruit trees, and bamboo surround the cottage. The covered lanai and small yard create a peaceful and private setting. With close proximity to the beach and restaurants, the location is perfect for those that do not want to drive.
$250 per night
4.96 out of 5 average rating, 96 reviews
Superhost
Cottage in Kailua
Kailua Cottage - Private Home Close to Beach& Town
Completely Remodeled 2 Bedroom Steps to the Beach - less than 10 blocks from Kailua Town! Air Conditioned with all new furniture, linens, and kitchen appliances! This unique style cottage has one CA King size bed, a large second room with a King bed and futon, a full size fully equipped kitchen with a dining table, & one full bath! There is NO living room, but there is a dining nook with bench seats. We also offer a new private washer & dyer, charcoal BBQ, an outdoor shower, and backyard patio.
$463 per night
4.74 out of 5 average rating, 86 reviews
Guest favorite
Cottage in Haleiwa
Tiny Home Steps to the beach 30 day minimum
Our clean, private and peaceful Tropical Tiny Home, nestled next to the Park. This is the perfect retreat while exploring the North Shore of Oahu. Fall asleep in your air-conditioned room to the sound of ocean waves and wake to the sound of tropical birds and wild chickens singing in the park. It doesn't get any more local than this! This is an island oasis, away from the hustle and bustle but only 1/2 mile to Haleiwa.Equipped with your basic necessities and ACROSS the street from the beach.
$91 per night
4.92 out of 5 average rating, 276 reviews

Popular amenities for Kailua cottage rentals

Cottage rentals with a hot tub

Guest favorite
Cottage in Kailua
Coconut Cabana: Studio/1ba near beach w/pool + spa
$98 per night
4.7 out of 5 average rating, 10 reviews
Guest favorite
Cottage in Kailua
Kailua Beach footsteps away
$185 per night
4.95 out of 5 average rating, 147 reviews
Cottage in Hauula
Beach Cottage
$116 per night
4.69 out of 5 average rating, 35 reviews
Superhost
Cottage in Kailua
Work from paradise! 1bd/1ba w/pool + spa
$170 per night
4.67 out of 5 average rating, 12 reviews
Guest favorite
Cottage in Kailua
Ginger Gazebo: 1bd/1ba near the beach w/pool + spa
$170 per night
4.71 out of 5 average rating, 14 reviews
Guest favorite
Cottage in Kailua
Kailua Beachside Cottage
$300 per night
4.99 out of 5 average rating, 85 reviews

Pet-friendly cottage rentals

Superhost
Cottage in Kaneohe
Welcome to our Maluhia - ocean front serenity home
$298 per night
4.89 out of 5 average rating, 96 reviews
Superhost
Cottage in Honolulu
Private/Quiet/Pet Friendly near UH Manoa/Waikiki
$99 per night
5.0 out of 5 average rating, 4 reviews
Guest favorite
Cottage in Haleiwa
2 Bedroom Ocean View Cottage. Walk to great Surf!
$375 per night
4.8 out of 5 average rating, 84 reviews
Superhost
Cottage in Kailua
Beautiful and Cheerful Hale Mokolea in Lanikai
$244 per night
New place to stay
Cottage in Waianae
Country 3-bedroom cottage 581 feet from the beach
$239 per night
4.67 out of 5 average rating, 9 reviews
Guest favorite
Cottage in Haleiwa
Plantation cottage in the heart of Haleiwa!
$456 per night
4.76 out of 5 average rating, 45 reviews
Cottage in Waimanalo
Waimanalo Beach Cottage 4
$405 per night
4.83 out of 5 average rating, 6 reviews
Cottage in Waimanalo
Waimanalo Beach Cottage 5
$424 per night
4.5 out of 5 average rating, 4 reviews
Cottage in Waimanalo
Waimanalo Beach Cottage 9 Studio with Kitchenette
$320 per night
New place to stay
Cottage in Waimanalo
Waimanalo Beach Cottage 1
$411 per night
4.0 out of 5 average rating, 3 reviews
Cottage in Waimanalo
Waimanalo Beach Cottage 3
$430 per night
4.38 out of 5 average rating, 8 reviews
Cottage in Waimanalo
Waimanalo Beach Cottages 6
$430 per night
New place to stay

Private cottage rentals

Guest favorite
Cottage in Kailua
Kailua Ohana Cottage close to beach
$315 per night
4.91 out of 5 average rating, 34 reviews
Guest favorite
Cottage in Honolulu
Clay Hale
$165 per night
5.0 out of 5 average rating, 18 reviews
Guest favorite
Cottage in Haleiwa
Tiny living! Quaint Haleiwa cottage
$175 per night
4.96 out of 5 average rating, 82 reviews
Guest favorite
Cottage in Honolulu
Cottage with Private pool
$161 per night
5.0 out of 5 average rating, 41 reviews
Superhost
Cottage in Hauula
Sacred Falls Studio 30 Day Minimum
$197 per night
4.9 out of 5 average rating, 81 reviews
Guest favorite
Cottage in Waianae
Stargazing Mountainside Cottage by Pristine Beach
$458 per night
4.98 out of 5 average rating, 43 reviews
Superhost
Cottage in Waiʻanae
MAKAHA SURF BEACH - Oahu, HI
$175 per night
4.91 out of 5 average rating, 64 reviews
Guest favorite
Cottage in Honolulu
Cool Studio Cottage House
$79 per night
4.82 out of 5 average rating, 77 reviews
Superhost
Cottage in Honolulu
Mikaela’s Cottage
$445 per night
4.7 out of 5 average rating, 10 reviews
Guest favorite
Cottage in Kailua
Beachhouse Kailua: Cottage with Green A/C
$249 per night
4.96 out of 5 average rating, 106 reviews
Cottage in Haleiwa
Sunset Backyards Hula Hut beachfront yard 30nights
$325 per night
4.7 out of 5 average rating, 166 reviews
Guest favorite
Cottage in Waimanalo
HONU HALE Beachfront Cottage!
$276 per night
4.89 out of 5 average rating, 45 reviews

Destinations to explore

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