Luxury Hawaiian Vacation Rentals 
Kailua, Oahu's Finest Luxury Vacation Rentals
A Piece of Heaven
5 BR/5 BA Maximum guests: 10
$30,000/month
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.
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5 BR/5 BA Maximum guests: 10
$30,000/month
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.
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A Place on the Beach
5 BR/5.5 BA Maximum guests: 14
$1500/night
A beautiful Kailua beachfront home! The perfect place to kick back and relax. The dining/living room opens out to breathtaking Kailua beach.
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5 BR/5.5 BA Maximum guests: 14
$1500/night
A beautiful Kailua beachfront home! The perfect place to kick back and relax. The dining/living room opens out to breathtaking Kailua beach.
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Beachfront Beauty
5 BR/5.25 BA Maximum guests: 10
$49,500 and up/month
New luxury interiors, spacious oceanfront yard, lagoon pool, interior courtyard, landscaped tropical gardens with waterfall, outdoor/indoor space, and game room. Completely remodeled in 2010!
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5 BR/5.25 BA Maximum guests: 10
$49,500 and up/month
New luxury interiors, spacious oceanfront yard, lagoon pool, interior courtyard, landscaped tropical gardens with waterfall, outdoor/indoor space, and game room. Completely remodeled in 2010!
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Hale Honu
5 BR/5 BA Maximum guests: 10
$1,350/night
A large, airy five-bedroom, five-bath beach house on world famous Kailua Beach on Oahu. Named after the sea turtles that populate the area, Hale Honu features a large swimming pool, panoramic ocean views and a rolling front lawn.
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5 BR/5 BA Maximum guests: 10
$1,350/night
A large, airy five-bedroom, five-bath beach house on world famous Kailua Beach on Oahu. Named after the sea turtles that populate the area, Hale Honu features a large swimming pool, panoramic ocean views and a rolling front lawn.
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Helen's Beach House
5 BR/5 BA Maximum guests: 12
$850/night
Helen's Beach House is a fabulous five-bedroom, five-bath family house that sits 4 houses back from world-famous Kailua beach. On a private road, with private access to the beach.
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5 BR/5 BA Maximum guests: 12
$850/night
Helen's Beach House is a fabulous five-bedroom, five-bath family house that sits 4 houses back from world-famous Kailua beach. On a private road, with private access to the beach.
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Kailua Alii
7 BR/7.5 BA Maximum guests: 12
$8,665/night
One of the newest and most striking contemporary executive beachfront estates on world-renowned Kailua beach. The estate features two homes (main house and guest house) separated by a resort-style pool with elegant umbrellas and lounge furnishings.
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7 BR/7.5 BA Maximum guests: 12
$8,665/night
One of the newest and most striking contemporary executive beachfront estates on world-renowned Kailua beach. The estate features two homes (main house and guest house) separated by a resort-style pool with elegant umbrellas and lounge furnishings.
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Kailua Bay Hale
5 BR/5.5 BA Maximum guests: 10-14
$3,500 and up/night
Kailua Bay Hale is a rare beachfront jewel offering spacious plantation-style living reminiscent of old Hawaii, with a kitchen suited for a master chef, a dining room and great room suited for lavish entertaining, a secluded lagoon-style pool, and more.
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5 BR/5.5 BA Maximum guests: 10-14
$3,500 and up/night
Kailua Bay Hale is a rare beachfront jewel offering spacious plantation-style living reminiscent of old Hawaii, with a kitchen suited for a master chef, a dining room and great room suited for lavish entertaining, a secluded lagoon-style pool, and more.
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Kailua Beach Estate
6 BR/4 BA Maximum guests: 11
$1,595/night
Six bedrooms (including two master suites) and four baths in 3500 square feet of beachfront living in Kailua. Swimming pool, gourmet kitchen, outdoor shower and all the amenities.
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6 BR/4 BA Maximum guests: 11
$1,595/night
Six bedrooms (including two master suites) and four baths in 3500 square feet of beachfront living in Kailua. Swimming pool, gourmet kitchen, outdoor shower and all the amenities.
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Kailua Oahulani
9 BR/9.5 BA Maximum guests: 20
$6,000 and up/night
A world-class property located on Kailua Beach on Oahu with full kitchen, bar, custom pool, washer/dryer, personal chef, maid service twice a week, and more.
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9 BR/9.5 BA Maximum guests: 20
$6,000 and up/night
A world-class property located on Kailua Beach on Oahu with full kitchen, bar, custom pool, washer/dryer, personal chef, maid service twice a week, and more.
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Kamaiiana Hale
3 BR/3 BA
Maximum guests: 6
$12,375/month
A spectacular 3-bedroom, 3-bath 100% fully air-conditioned home on one of the nicest private lanes beachside with private gated access to Kailua beach.
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Ke Kala Kailua
4 BR/3 BA Maximum guests: 8
$850/night
A four-bedroom, three-bath executive retreat and beachfront rental on Kailua Beach. Fabulous ocean views. Colorful island-style rattan furnishings and central air conditioning throughout the home.
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4 BR/3 BA Maximum guests: 8
$850/night
A four-bedroom, three-bath executive retreat and beachfront rental on Kailua Beach. Fabulous ocean views. Colorful island-style rattan furnishings and central air conditioning throughout the home.
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Lani Lehua
4 BR/3 BA Maximum guests: 9
$1,500/night
Right on Kailua Beach! Features a full kitchen, air-conditioned bedrooms and office with wireless broadband. Includes a shared pool, outdoor spa and heated outdoor shower.
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4 BR/3 BA Maximum guests: 9
$1,500/night
Right on Kailua Beach! Features a full kitchen, air-conditioned bedrooms and office with wireless broadband. Includes a shared pool, outdoor spa and heated outdoor shower.
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Sunshine Moonrise
3 BR/3 BA Maximum guests: 6
$745/night
An oceanfront vacation home at Kailua Beach. Features a full kitchen and dining area, swimming pool. Three bedrooms and baths providing comfortable accommodations for up to six guests.
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3 BR/3 BA Maximum guests: 6
$745/night
An oceanfront vacation home at Kailua Beach. Features a full kitchen and dining area, swimming pool. Three bedrooms and baths providing comfortable accommodations for up to six guests.
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The Kailua Beach House
9 BR/5.5 BA Maximum guests: 18
$2,150/night
A seven-bedroom vacation house plus a separate two-bedroom cottage surrounding a swimming pool on this large, beachfront lot. The perfect accommodation for large groups of up to 18 guests.
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9 BR/5.5 BA Maximum guests: 18
$2,150/night
A seven-bedroom vacation house plus a separate two-bedroom cottage surrounding a swimming pool on this large, beachfront lot. The perfect accommodation for large groups of up to 18 guests.
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Villa Kailua
6 BR/5 BA Maximum guests: 12
$1,350/night
A stunning six-bedroom kamaʻāina Oahu beachfront home on Kailua Beach. 3100 square feet of upscale elegance—gourmet kitchen, swimming pool, private sauna and Jacuzzi, and much more.
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6 BR/5 BA Maximum guests: 12
$1,350/night
A stunning six-bedroom kamaʻāina Oahu beachfront home on Kailua Beach. 3100 square feet of upscale elegance—gourmet kitchen, swimming pool, private sauna and Jacuzzi, and much more.
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Absolute Hawaii luxury vacation homes is a vacation rental listing site and is not a realtor nor does it sell, manage properties or engage in real estate transactions. We act as an intermediary between vendors who list their properties on our site and guests who rent the properties. Therefore, all pricing terms are determined by the individual vendor and are subject to change.
All Absolute Hawaii rentals are subject to varying minimum night requirements, typically a 30-night minimum.
Rental Rates do not include taxes, cleaning fees, booking fees, or security deposits. These charges are additional.