Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Condos
Cottages
Estates
Homes
Studios
Villas
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Farmhouses
Hotels
Lodges
Townhomes
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Kailua Ocean Vacation Rentals Vacation Rentals(82)

82 Results
$900 - $1,950
per night
5 - 14 night minimum stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 14
5 - 14 night minimum stay
(29)
  • Studio,
  • 1 BA,
  • Sleeps 3
3 night minimum stay
(26)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
(22)
  • 1 BR,
  • 1 BA,
  • Sleeps 3
(21)
$210 - $225
per night
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
3 night minimum stay
(8)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
5 night minimum stay
(68)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
(48)
$7,000 - $14,000
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
(20)
$275 - $325
per night
6 - 14 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
6 - 14 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
5 night minimum stay
(13)
$4,900 - $7,700
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night minimum stay
(26)
$349 - $549
per night
5 - 10 night minimum stay
  • 3 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 8
5 - 10 night minimum stay
2 Reviews
  • 4 BR,
  • 4 BA,
  • Sleeps 8
(9)
$38,500 - $52,500
per week
7 - 14 night minimum stay
  • 10 BR,
  • 3 BA,
  • Sleeps 18
7 - 14 night minimum stay
$6,300 - $12,075
per week
7 - 14 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 13
7 - 14 night minimum stay
$8,750 - $19,250
per week
7 - 14 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 - 14 night minimum stay
$11,690 - $15,575
per week
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
7 night minimum stay
$13,300 - $30,625
per week
7 - 14 night minimum stay
  • 3 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 7
7 - 14 night minimum stay
$235 - $300
per night
5 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
5 - 7 night minimum stay
(8)
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 17
5 night minimum stay
(13)
$5,950
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(5)
$5,810
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
7 night minimum stay
(5)
$225 - $300
per night
5 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
5 - 7 night minimum stay
(6)
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 8
(4)
$275 - $290
per night
2 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(18)
  • 4 BR,
  • 2 BA,
  • Sleeps 7
7 night minimum stay
(20)
$3,465 - $6,965
per week
7 - 14 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 - 14 night minimum stay
(15)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
5 night minimum stay
2 Reviews
$5,565 - $9,800
per week
14 - 30 night minimum stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 15
14 - 30 night minimum stay
(3)
Advertisement
 

Recent Kailua Reviews

Home Away From Home

5 of 5
Our family (four adults, two children) stayed here for not quite two weeks. I LOVE this house. Not just "this is a great vacation rental" but if I were forced to live in Hawaii, I would buy this place in a heartbeat - furniture intact. It has so much character and charm, warmth and soul. I'm very impressed that in spite of its high ceilings (something I usually don't like in a home) it is very cozy and (as my five-year-old would say) "cuddly." It is a home rather than just a house. Our children (and we) greatly enjoyed the beautiful pool. In fact, my younger son enjoyed it more than the beach (though the rest of us preferred the quick, easy walk to the beautiful (and uncrowded) beach nearby). And the banyan tree is staggeringly magnificent. There's so much outdoor seating - it's wonderful for reading, eating, or just relaxing. The house is full of gorgeous details - wood floors, the chandelier and fireplace, and a lot of traditional Hawaiian touches. The showers are fantastic. There were also a few books, toys, and games for our kids. Also, Leah and Gudrun were both great. Gudrun was excellent at keeping in contact with us before our arrival (and her restaurant recommendation was the best meal we had in Kailua). Leah was friendly, warm, and welcoming. If we ever come back to Oahu, I would definitely schedule our trip around your availability, because I can't see why I would stay anywhere else.
  • Submitted: Oct 3, 2014
  • Stayed: Sep 2014

Kailua Lani

5 of 5
The three couples that stayed here loved the place and will probably return. We silly people went into Waikiki one day and realized we needed to get back to our little bit of Kailua Heaven ASAP. Everything we needed was already here, so it was like coming home.....but with a lovely pool and a small family of geckos. Our thanks to Judy for letting us stay.
  • Submitted: Sep 22, 2014
  • Stayed: Sep 2014

Life doesn't get any better!

5 of 5
This vacation was to celebrate our 50th wedding anniversary, accompanied by grown up children and grandchildren. It was the first time we ever rented a vacation home, but I seriously doubt if we could have chosen a better house or more genial host. Most of what I wanted to say has already been said by others, so will add that just taking in the scenery through the glass walls while relaxing comfortably in the upstairs living room of this beautiful plantation style home, or from its lanai, seemed to make all the cares of the world fade away. The house is right on the beach, unlike most others around the bay, which are set back some distance, so we had a grandstand view of the beach and ocean. Just imagine falling to sleep at night and then waking up in the morning to the sound of the crashing surf just feet away from your bedroom window, or slipping down to the beach, morning coffee in hand to enjoy the sunrise, or watching the grandkids play with the boogie boards and other toys in the clear aquamarine ocean water. Life doesn’t get any better! Dan couldn’t do enough for us. He made sure we had all we needed, yet remained completely unobtrusive.
  • Submitted: Aug 2, 2014
  • Stayed: Jun 2014