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Vacation rentals in Kailua

Vacation rentals in Kailua

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Kailua

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

  • Kailua Private Detached Cottage/30 days minimum
    SUPERHOSTEntire guesthouse · 2 guests · 1 bed · 1 bath
    Kailua Private Detached Cottage/30 days minimum

    Island style living fully furnished detached 1 bedroom/1 bath cottage. Short walk (around 10 minutes) to Kailua town with stores and restaurants and beautiful white sandy beach. Comfortable, private, clean, with amenities and queen size bed, fully stocked kitchenette, washer/dryer on site, private covered carport, AC in the bedroom and ceiling fans with double panel windows. Outdoor has an easy to use gas grill with private dinning and sitting area by the garden. Not ideal for children.

    What guests are saying:

    “We had a wonderful time at Wen’s place in Kailua. The location was perfect - not too far to drive down to Waikiki, but far enough from the hustle and bustle of the touristy areas to give us a more authentic Hawaiian experience. We loved the beach gear - chairs, umbrella, body boards, etc. and really made use of it. We spent a lot of time at Kailua, Lanikai and Waimānalo beaches and did also did a few hikes around. Everything is just a short drive away. On a couple of nights we also walked to the Kailua town centre - less than a 15 min walk and very enjoyable. The place itself was very clean and had everything we needed - decorated in traditional Hawaiian style which added to it’s charm. Wen had a lot of great recommendations for things to do and places to visit, we are very grateful for her advice. I would definitely recommend this place to any of my friends visiting Oahu!”

  • Secluded Kailua Beach Bungalow with Private Garden
    SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
    Secluded Kailua Beach Bungalow with Private Garden

    Aloha! We renovated this old-style Hawaiian home so that it will have the charm of old Hawaii with modern conveniences. The Bungalow is on the first floor of the home with it's own private parking, private entry and private garden - completely secluded - the only shared space is the laundry room which is shared with one other bungalow. This garden oasis is in the most awesome location - you are 100 steps from the famous soft white-sand of Kailua Beach.

    What guests are saying:

    “This was our second stay to Cheri’s paradise on the beautiful Kailua Beach. Her garden feels like a private tropical oasis and the ocean is just a few steps right outside the back gate. Cheri has everything you need for the beach and a goodie basket with Hawaiian fruit and treats, as well as, cold beer in the fridge. The location feels secluded, but is close to everything Hawaiian that you could want! Cheri has all the details included!”

  • MUST LOVE DOGS, the Ocean Room.
    SUPERHOSTPrivate room · 2 guests · 2 beds · 1 shared bath
    MUST LOVE DOGS, the Ocean Room.

    Quiet, clean and relaxing space in my home in the Olomana subdivision at the base of Mt. Olomana in lovely and coveted Kailua. Spectacular views of Mt. Olomana. To stay here though, you must be a dog lover because you'll be greeted by Daizee (golden retriever), Murphy (chocolate lab) and Lulu (bordoodle (border collie/poodle)), my welcoming party. This room has a comfy twin bed with a memory foam mattress and also a comfortable roll-a-way bed which also has a memory foam mattress.

    What guests are saying:

    “Perhaps the best place I’ve ever stayed. On the surface, Susan’s house is sparkling clean and well kept. Many amenities were provided (including towels, shampoo, coffee) for us. Susan even has a binder with activity recommendations. On a deeper level, Susan is perhaps the most wonderful woman I’ve ever met. Staying with her and her beautiful dogs was one of the highlights of my trip. I recommend her place to anyone wanting more than just a place to stay and Susan made her home feel like my home.”

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Popular amenities for Kailua vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Kailua

Beach House Bedroom
SUPERHOSTPrivate room
Beach House Bedroom
Price:$37 / night
Secluded Kailua Beach Bungalow with Private Garden
SUPERHOSTEntire apartment
Secluded Kailua Beach Bungalow with Private Garden
Price:$229 / night
South Seas Cottage Kailua
Entire house
South Seas Cottage Kailua
Price:$150 / night
Kailua Palm Studio. Walk to Beach! PERMITTED
SUPERHOSTEntire guesthouse
Kailua Palm Studio. Walk to Beach! PERMITTED
Price:$145 / night
Kailua Private Separate Studio/ 30 days minimum
SUPERHOSTEntire guest suite
Kailua Private Separate Studio/ 30 days minimum
Price:$69 / night
MUST LOVE DOGS, the Ocean Room.
SUPERHOSTPrivate room
MUST LOVE DOGS, the Ocean Room.
Price:$55 / night
Tropical Garden Cottage
SUPERHOSTEntire cottage
Tropical Garden Cottage
Price:$67 / night
Mahealani's Hale
SUPERHOSTEntire house
Mahealani's Hale
Price:$150 / night
Private Studio Apartment near beach
SUPERHOSTEntire loft
Private Studio Apartment near beach
Price:$195 / night
Cozy Private Guest Suite Next to Beach With Pool
SUPERHOSTEntire house
Cozy Private Guest Suite Next to Beach With Pool
Price:$140 / night
Holiday Palms-2 blks fr Kailua Bch/walk to town
Entire guesthouse
Holiday Palms-2 blks fr Kailua Bch/walk to town
Price:$145 / night
Nani Hale
SUPERHOSTEntire guest suite
Nani Hale
Price:$130 / night
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