Kailua Vacation Rentals

Kailua is one of the most famous vacation rental destinations on Oahu, featuring a fantastic white-sand beach. Many of the vacation rental properties in Kailua are oceanfront, which makes Kailua the perfect destination for those looking for privacy or a romantic getaway. You can have your privacy here and in the same time enjoy easy access to shopping malls, restaurants and services. Kailua Beach is ideal for swimming, kayaking and windsurfing and was nominated the best beach in the U.S. by Condé Nast magazine in 1998.

  • Nice Studio. Covered Patio. 3 Blks To Beach. Air Cond. Wifi. Parking. Pay Washer

    Studio unit in a private home. Private entrance and private bathroom. Quiet, laid back owners prefer similar, like minded guests. Air conditioner, ceiling fan. Free parking, WIFI and bike use. Pay washer, dryer on property. No singles parti...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    85 USD - 92 USD

    nightly

    575 USD - 630 USD

    weekly

    2,250 USD - 2,500 USD

    monthly

  • Honu Haven: A Tropical Garden Setting with a Pool

    Honu Haven is just a 10 minute walk to Kailua Town and world famous Kailua Beach where windsurfers, kiteboarders and beachcombers from around the world converge to enjoy the beautiful water. In Kailua Town there is great dining and shopping. Ke...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    125 USD - 125 USD

    nightly

    875 USD - 875 USD

    weekly

  • Kailua Beachfront -Charming,Private, Hawaiian Style Home

    Featured in Coastal Living as guest house of the month, this private Kailua beachfront estate is nestled in among almost 50 coconut tress and lush tropical gardens. With over 700 feet of ancient lava rock wall surrounding this original 1930's Haw...

    3 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua

    550 USD - 800 USD

    nightly

    5,600 USD - 5,600 USD

    weekly

  • Majestic Island Home with new pool, perfect for families and close to beach

    Beautiful Brand New Pool is the gathering spot of this majestic island home. Serene and lush landscape, newly built home offers the perfect floor plan to accommodate large groups boasting 3,300 sf of living space with vaulted ceilings and spaciou...

    9 Bedrooms, 5 Bathrooms, Sleeps 22

    HI>Kailua

    1,135 USD - 1,685 USD

    nightly

    7,945 USD - 7,945 USD

    weekly

  • Spectacular Kailua Beachfront Estate

    Located on the most pristine beach in all of Oahu and just 20 minutes from the airport/Waikiki, this spectacular custom estate is a stunning beachfront architectural masterpiece. As you approach the home, you are greeted by a contemporary gated en...

    4 Bedrooms, 6 Bathrooms, Sleeps 10

    HI>Kailua

    3,200 USD - 3,200 USD

    nightly

    60,000 USD - 60,000 USD

    monthly

  • 3/1 Newly Remodeled Duplexed Home. Walking distance to Everything!

    3 bedroom 1 bath newly remodeled house. Large enclosed yard. Walking distance to Kailua town. Less than 1 mile from Kalama Beach Park. ...

    3 Bedrooms, 1 Bathrooms, Sleeps 6

    HI>Kailua

  • 5 Minute Walk to Kailua Beach

    Our place is a one bedroom and one bathroom studio. It is about 720 sq ft. It's tastefully decorated with ample sittings in the living room. Vaulted ceiling makes the unit feel very spacious and airy. It has a very quiet split system air condi...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

  • Kailua Beach Hideaway

    Live the Kailua Lifestyle in this 3 bedroom home that is just one block to the beach. New remodeled open kitchen and bath in late 2016 give this home the modern comforts we all enjoy. Even with the famous tradewinds blowing, Hawaii can be a bit w...

    3 Bedrooms, 1 Bathrooms, Sleeps 6

    HI>Kailua