Vacation Rentals Hawaii  »  Oahu »  Kailua

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A Piece of Heaven

A Piece of Heaven is five bedrooms of beach front paradise in Kailua. Swimming pool, jacuzzi, game and tv room make this property an ideal vacation recreation destination. Monthly rentals only More

$ 50,000 /
Month


» Location: Kailua
» Bed(s): 6
» Bath(s): 5 1/2
» Sleeps: 12


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A Place on the Beach

A Place on the Beach is a five bedroom five-and-a-half bath Oahu vacation rental beach house situated in the exclusive Hale Kai Surf and Racquet Resort at Kailua Beach, Oahu, Hawaii. 4500 sq. ft. of paradise... More

$ 1,500 (seasonal) and up /
Night


» Location: Kailua
» Bed(s): 5
» Bath(s): 5.5
» Sleeps: 12
» Full Kitchen!

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A Walk to the Beach Cottage

Just a short walk brings you to world famous Kailua Beach. Walk to the Beach Cottage is a one bedroom one bath cottage that may be combined with Walk to the Beach House for groups up to eight. The cottage,... More

$ 175 /
Night


» Location: Kailua
» Bed(s): 1
» Bath(s): 1
» Sleeps: 2


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Kailua Beach

A Walk to the Beach House

A Walk to the Beach House is a charming three bedroom, two bath vacation house located very close to the heart of Kailua town. Just a short fifteen minute walk to Kailua Beach and a two minute walk to... More

$ 395 /
Night


» Location: Kailua
» Bed(s): 3
» Bath(s): 2
» Sleeps: 6
» Full Kitchen!

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A Walk to the Beach House & Cottage

A Walk to the Beach House is a charming three bedroom, two bath vacation house located very close to the heart of Kailua town. Combined here with Walk to the Beach Cottage for groups up to eight. Just... More

$ 570.00 /
Night


» Location: Kailua
» Bed(s): 4
» Bath(s): 3
» Sleeps: 8
» Full Kitchen!

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Relax by the pool

Beach Corner

Beach Corner is a beachside private retreat just steps to Kailua Beach. The indoor-outdoor floor plan features a private courtyard and the home opens to the covered poolside lanai. The recent remodel to... More

$ 1,795 and up /
Night


» Location: Kailua
» Bed(s): 7
» Bath(s): 4.5
» Sleeps: 14
» Full Kitchen!

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Beach Side Beauty

A charming four Bedroom two bathroom home just a few houses from the beach. This home is situated on a private beach lane in the town of Kailua, Oahu. You will adore this vacation rental, your stay will... More

$ 550 /
Night


» Location: Kailua Beach, Oahu
» Bed(s): 4
» Bath(s): 2
» Sleeps: 7
» Full Kitchen!

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Birdsong

This Historic Residence was built in 1907. It is a two-story solid redwood house, (both exterior and all interior walls are redwood plank–not reproducible today) with a unique craftsman style design.... More

$ 520 /
Night


» Location: Honolulu
» Bed(s): 3
» Bath(s): 2
» Sleeps: 6
» Full Kitchen!

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Bob’s Turtle House

Bob's Turtle House is a three bedroom two-and-a-half bath ocean front house in Makaha. Large lawn, great views of the deep blue ocean and fabulous sunsets. Just seven minute walk to nearest beach access. More

$ 812.50 and up /
Night


» Location: Makaha
» Bed(s): 3
» Bath(s): 3
» Sleeps: 6
» Full Kitchen!

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Caroline’s Beachside House

Caroline's Beachside House is an exquisite Oahu vacation rental located on a private beachside lane steps from Kailua Beach. It provides island living at its best. Air conditioned throughout. Swimming... More

$ 875 /
Night


» Location: Kailua
» Bed(s): 5
» Bath(s): 2.5
» Sleeps: 10
» Full Kitchen!

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Covered Lanai

East Side Ocean Sweetheart

East Side Ocean Sweetheart is a magnificent Hawaii Kai, Oahu property with a swimming pool and fenced yard right on the beach. Newly remodeled and decorated with elegant and modern interiors More

$ 2,200 /
Night


» Location: Hawaii Kai
» Bed(s): 4
» Bath(s): 4.5
» Sleeps: 7
» Full Kitchen!

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Relaxing open spaces that invite beautiful outdoors in

Estate on the Beach

With the Mokulua Islands as the backdrop in a setting of unspeakable beauty, this estate is the dream home of the late Paul Mitchell, who created it with a powerful sense of what is timeless, exquisite,... More

$ 4,600 and Up /
Night


» Location: Lanikai
» Bed(s): 7
» Bath(s): 6 full, 5 half
» Sleeps: 14
» Full Kitchen!

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Garden Villa

A gorgeous very private house all to yourself. Beautiful two bedroom, two bath home. Lovely bedroom with views of Diamond Head and Honolulu. Perfect villa for professionals who work in Honolulu or a great... More

$ 10,000 /
Month


» Location: Honolulu
» Bed(s): 3
» Bath(s): 2
» Sleeps: 6
» Full Kitchen!

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Hale Honu

Hale Honu is a large, airy five bedroom five bath Hawaii vacation rental beach house on world famous Kailua Beach on Oahu. Named after the sea turtles that populate the area, Hale Honu features a large... More

$ 25,000 /
Month


» Location: Kailua
» Bed(s): 5
» Bath(s): 5
» Sleeps: 10
» Full Kitchen!

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Lanai shaded by gorgeous banyan tree with ocean view

Hawaii Kai Beach Front

Hawaii Kai Beach Front is comprised of a three bedroom main house and a two bedroom separate vacation cottage. Situated on 100 feet of beach front in Hawaii Kai for spectacular sunsets and tropical views.... More

$ 1200 and up /
Night


» Location: East Oahu
» Bed(s): 5
» Bath(s): 4.5
» Sleeps: 10
» Full Kitchen!

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Sparkling private pool

Hawaii Kai Ohana

Hawaii Kai Ohana is a two-story family style vacation rental home nestled on the slopes of Koko Head in Hawaii Kai. Great ocean views and a swimming pool. Sleeps eight to ten guests. More

$ 760 /
Night


» Location: East Oahu
» Bed(s): 3+
» Bath(s): 3
» Sleeps: 8-10
» Full Kitchen!

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Holiday at Diamond Head

Holiday at Diamond Head

Holiday at Diamond Head, remodeled in 2009, is an elegant, contemporary home with beautiful architectural design and panoramic ocean views in a private tropical setting. The perfect perch for ocean watching... More

$ 2,000 /
Night


» Location: Diamond Head
» Bed(s): 4
» Bath(s): 4
» Sleeps: 8
» Full Kitchen!

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Private Pool

Home Sweet Home

Home Sweet Home is a two bedroom, two bath vacation home just minutes from Kailua Beach. This spectacular home features three full living areas, a full kitchen, pool with backyard, internet access, covered... More

$ 465 /
Night


» Location: Kailua
» Bed(s): 2
» Bath(s): 2
» Sleeps: 4


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Relax in garden setting next to private pool

Kahala Hale

Kahala Hale is a wonderful four bedroom, three bath Oahu vacation home rental in Kahala with a beautiful swimming pool. There's a big screen TV, DVD, stereo, two separate dining areas and lots of living... More

$ 900 /
Night


» Location: East Oahu
» Bed(s): 4
» Bath(s): 3
» Sleeps: 8
» Full Kitchen!

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Relax poolside at Kahala Moon Resort or step from yard to Kahala Beach

Kahala Moon Resort

Kahala Moon Resort This spacious private estate situated on manicured beachfront grounds has something for everyone! Two swimming pools, a tennis court, and a large jacuzzi. The interior is furnished with... More

$ 3950 & up /
Night


» Location: East Oahu
» Bed(s): 7
» Bath(s): 6
» Sleeps: 14
» Full Kitchen!

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View of Beach from the House

Kailua Bay Hale

Located on the windward side of Oahu, Kailua Bay Hale is a rare beachfront jewel offering plantation-style living reminiscent of old Hawaii and elegant furnishings from around the world. A dream come true,... More

$ 3500 and up /
Night


» Location: Kailua
» Bed(s): 5
» Bath(s): 5.5
» Sleeps: 10-14
» Full Kitchen!

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Kailua Beach Villa

Kailua Beach Villa is a beautiful luxury villa situated right on the beach. It has six bedrooms and 4 bathrooms a pool and unlimited access to the beach! More

$ 1995 /
Night


» Location: Kailua
» Bed(s): 6
» Bath(s): 4
» Sleeps: 10


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Kailua Beach Walk Cottage

Kailua Beach Walk House and Cottage combines two wonderful accommodations on one charming beach side property just around the corner from world famous Kailua Beach. The Cottage is a one bedroom one bath... More

$ 195 /
Night


» Location: Kailua
» Bed(s): 1
» Bath(s): 1
» Sleeps: 4
» Full Kitchen!

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Kailua Beach Walk House

Kailua Beach Walk House is a wonderful accommodation on a charming beach side property just around the corner from world famous Kailua Beach. The House is a three bedroom two bath unit sleeping six. ... More

$ 425 /
Night


» Location: Kailua
» Bed(s): 3
» Bath(s): 2
» Sleeps: 8
» Full Kitchen!

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Kailua Palms Estate Guest House

Kailua Palms Estate Guest House is a handsome two bedroom, two bath vacation rental in Kailua, Oahu, Hawaii with kitchen, large lanai, pool, washer and dryer. Wheelchair accessible. More

$ 395 /
Night


» Location: Kailua
» Bed(s): 2
» Bath(s): 2
» Sleeps: 4


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Kawela Bay Beach House

Kawela Bay Beach House is a charming private access north shore home on a secluded white sand beach. Lay back and relax in the oversize swing hammock or enjoy excellent snorkeling in front of the house. More

$ 450 /
Night

$ 3150 /
Week


» Location: North Shore
» Bed(s): 2
» Bath(s): 1
» Sleeps: 4
» Full Kitchen!

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Ke Kela Kailua – Vacation Rental Kailua, Hawaii

Ke Kela Kailua is a four bedroom three bath, executive retreat and beach front vacation home rental on Kailua Beach. Fabulous ocean views. Colorful island style rattan furnishings and central air conditioning... More

$ 1050 /
Night


» Location: Kailua
» Bed(s): 4
» Bath(s): 3
» Sleeps: 8
» Full Kitchen!

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Ketta’s Place

Ketta’s Place is a large, ocean front, non-smoking studio cottage with a full ocean view.  Located on a white sandy beach in Punalu’u, this fully furnished cottage will sleep three comfortably.... More

$ 135 /
Night


» Location: Punalu'u
» Bed(s): Studio
» Bath(s): 1
» Sleeps: 3
» Full Kitchen!

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Laie Beach Villa

Experience the beauty and charm of this one-of-a-kind, resort style home. The home is located on an amazing 25,000 sq/ft beach front property designed around a central courtyard area with pool, spa, bali... More

$ 2500 /
Night


» Location: Laie
» Bed(s): 4
» Bath(s): 4.5
» Sleeps: 8
» Full Kitchen!

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Stunning view of the Mokulua Islands

Lanikai Beach House

The Lanikai Beach House provides dramatic views of the sun coming up between the Mokulua Islands right from your living room of this recently renovated Lanikai getaway. The main house can comfortably sleep... More

$ 985 /
Night


» Location: Lanikai
» Bed(s): 4
» Bath(s): 3
» Sleeps: 9
» Full Kitchen!

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Beach-as seen from front-of-cottage

Lanikai Beachfront Cottage

Lanikai Beachfront Cottage is a comfortable beach/ocean front vacation rental cottage right in the center of beautiful Lanikai Beach on Oahu, Hawaii. The perfect spot for the ultimate family vacation or... More

$ 495 /
Night


» Location: Lanikai
» Bed(s): 2
» Bath(s): 1
» Sleeps: 4
» Full Kitchen!

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Lanikai Hale Beach Front

This beachfront family vacation rental home consists of main house and guest cottage located on a beautiful sandy beach in Lanikai. The ocean is protected by off-shore reefs offering safe swimming and... More

$ 1240 /
Night


» Location: Lanikai
» Bed(s): 4
» Bath(s): 4
» Sleeps: 8
» Full Kitchen!

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Loft in Kailua

Loft in Kailua is a charming one bedroom vacation rental suite with an extra large bathroom with tub and separate shower. Located in the Enchanted Lakes section of Kailua, Loft in Kailua is just three... More

$ 225 /
Night


» Location: Kailua
» Bed(s): 1
» Bath(s): 1
» Sleeps: 2


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Love Kahala! 5 bedroom Oahu vacation rental with pool

Love Kahala!

Love Kahala! is a private 5 bedroom, 4 bath luxury home in prestigious Kahala, Honolulu. Just minutes from the beach this home is designed to give you the ultimate indoor/outdoor island-style living experience.... More

$ 1,550 and up /
Night


» Location: Kahala
» Bed(s): 5
» Bath(s): 4
» Sleeps: 10
» Full Kitchen!

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Luxury at Diamond Head

Stunning beachfront home in Diamond Head. The Luxury at Diamond Head, located at the slopes of Diamond Head—Honolulu’s most prestigious neighborhood. This gorgeous beachfront property is truly suited... More

$ 4,455 /
Night


» Location: Diamond Head
» Bed(s): 5
» Bath(s): 4.5
» Sleeps: 10
» Full Kitchen!

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