279 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Kailua Vacation Rentals(279)

279 Results
$3,675 - $8,050
per week
7 - 14 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 - 14 night min stay
(17)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
(25)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
5 night min stay
(70)
  • 1 BR,
  • 1 BA,
  • Sleeps 3
(26)
  • Studio,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 3
(40)
  • Studio,
  • 1 BA,
  • Sleeps 4
(89)
$145
per night
3 night min stay
  • Studio,
  • 1 BA,
  • Sleeps 3
3 night min stay
(33)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night min stay
(13)
$325
per night
5 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
5 - 7 night min stay
(11)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
(31)
  • 5 BR,
  • 6 BA,
  • Sleeps 10
5 - 7 night min stay
(28)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night min stay
(5)
  • 3 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 8
5 - 10 night min stay
(3)
$250 - $500
per night
3 - 5 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night min stay
(38)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
(54)
  • Studio,
  • 1 BA,
  • Sleeps 2
5 night min stay
(12)
$275
per night
6 - 10 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
6 - 10 night min stay
$5,565 - $8,400
per week
7 - 14 night min stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
7 - 14 night min stay
(25)
  • Studio,
  • 3 BA,
  • Sleeps 7
3 night min stay
(4)
$296 - $444
per night
3 - 6 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 6 night min stay
(35)
$4,550 - $5,565
per week
7 - 14 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 - 14 night min stay
(18)
$279 - $300
per night
2 - 5 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 5 night min stay
(47)
$5,600 - $8,365
per week
7 night min stay
  • 8 BR,
  • 4 BA,
  • Sleeps 18
7 night min stay
(7)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
5 - 7 night min stay
(15)
$235 - $300
per night
5 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
5 - 7 night min stay
(11)
$350 - $550
per night
5 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
5 night min stay
(17)
$795 - $895
per night
6 - 10 night min stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 18
6 - 10 night min stay
(27)
  • 4 BR,
  • 4 BA,
  • Sleeps 8
(9)
  • 5 BR,
  • 5 BA,
  • Sleeps 14
5 - 10 night min stay
(26)
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 17
5 night min stay
(16)
 View map Map
Advertisement
 

Recent Kailua Reviews

Close, Clean and Comfortable!

5 of 5
If you haven't stayed in Kailua you are missing out and if you get to go stay here. The location for this guest home is right across from Kailua beach park - you walk out the back path and there you are. You have 2 rooms, a large kitchen, dining room, washer/dryer, and nice size patio. As it is connected to the larger home you occasionally hear folks but it is generally a very quiet and safe place. The value for the location is wonderful. Walk to Bob's pizza, the Market for a coffee, or Island Snow Shave Ice - our favorites :-) The owners will honor your privacy but also are so open to chatting if you want to ask for advice or directions. Our family of 4 enjoyed the beaches especially snorkeling in Lanikai (our favorite), hiking, and just beautiful mountain views of this area of Oahu. But if it is windy or rainy - remember it is never a long drive to another lovely beach or to Pearl Harbor (recommended). Thank you to our lovely hosts for sharing this clean and comfy home. I hope we never bothered you with our evening gecko hunting! We left our beach-dreaming hearts in Kailua - so if we come back we hope to stay here again!
  • Submitted: Apr 2, 2015
  • Stayed: Mar 2015

Could not have been more perfect!

5 of 5
My husband and I had the opportunity to stay in this amazing cottage. When we opened the gate it was like we has stepped into a luxury resort. The house was beautifully decorated and the gardens were breath taking. We enjoyed our mornings and evenings on the deck and the beach was just a few short minutes away. I would highly recommend Robert and Gundrun's cottage.
  • Submitted: Mar 22, 2015
  • Stayed: Feb 2015

Class Act!

5 of 5
From the beginning of my efforts to plan a Kailua vacation, Tricia was always very accommodating, helpful and truthful. As a result, it should not have been a surprise to see the little oasis that she and Eric have created, but it was. Frankly, the pictures do not do this one bedroom house justice. The residence and grounds were spotless, and my wife and I felt very much at home. It was hard to believe that the place was connected to the main house - and we both enjoyed the quiet and peaceful setting (augmented by a gorgeous koi pond right outside the window)! We cooked most of our meals in the house (kitchen is very well-supplied) and enjoyed most of them on the side patio. The location is only a few blocks from Kailua Beach (which, I may add, is probably the nicest beach I've ever visited!). I would not hesitate to rent this property again.
  • Submitted: Feb 16, 2015
  • Stayed: Feb 2015