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Vacation rentals in Kailua, Oahu, Hawaii

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  • Established history of renting online
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  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 89 Rentals in Kailua
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From
$352
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
14 photos Details
Reviews (5) Make Enquiry
From
$156
Per Night
Studio, 1 Bathroom, Sleeps 2
7 photos Details
Reviews (1) Make Enquiry
From
$853
Per Night
8 Bedrooms, 4 Bathrooms, Sleeps 18
18 photos Details
Reviews (3) Make Enquiry
Also consider
Maluhia villa offers lagoon shaped pool with waterfall & Hot tub, short walk to beach
4 Bedrooms, sleeps 8
$1,545 - $2,931 / night
Royal Kailua Estate
8 Bedrooms, sleeps 16
$6,395 - $12,790 / night
Royal Kailua Estate - Upscale Private Beachfront Resort with Stunning Courtyard
7 Bedrooms, sleeps 14
$6,395 - $12,790 / night
Ke'aloha - Beachside cottage
4 Bedrooms, sleeps 6
$826 / night
From
$160
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
18 photos Details
Reviews (8) Make Enquiry
From
$191
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
16 photos Details
Reviews (1) Make Enquiry
From
$155
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
22 photos Details
Reviews (9) Make Enquiry
From
$134
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
16 photos Details
Reviews (4) Make Enquiry
From
$282
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
13 photos Details
Reviews (12) Make Enquiry
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From
$304
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 20
26 photos Details
Reviews (12) Make Enquiry
From
$421
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 7
16 photos Details
Reviews (23) Make Enquiry
From
$84
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
25 photos Details
Reviews (1) Make Enquiry
From
$425
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 10
16 photos Details
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From
$266
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
31 photos Details
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From
$272
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
18 photos Details
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From
$101
Per Night
Studio, 1 Bathroom, Sleeps 2
10 photos Details
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From
$213
Per Night
Studio, 1 Bathroom, Sleeps 3
16 photos Details
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From
$176
Per Night
Studio, 1 Bathroom, Sleeps 2
30 photos Details
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From
$160
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
21 photos Details
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From
$148
Per Night
Studio, 1 Bathroom, Sleeps 3
8 photos Details
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From
$101
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
Reviews (1) Make Enquiry
From
$185
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
21 photos Details
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From
$85
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
23 photos Details
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From
$176
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
24 photos Details
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From
$128
Per Night
Studio, 1 Bathroom, Sleeps 2
14 photos Details
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From
$187
Per Night
Studio, 1 Bathroom, Sleeps 4
14 photos Details
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From
$160
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
15 photos Details
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From
$453
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
18 photos Details
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From
$240
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
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From
$213
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
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From
$157
Per Night
Studio, 1 Bathroom, Sleeps 3
17 photos Details
Reviews (20) Make Enquiry
From
$506
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
14 photos Details
Reviews (2) Make Enquiry
From
$320
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
Reviews (15) Make Enquiry
From
$1,119
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
31 photos Details
Reviews (3) Make Enquiry
From
$171
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
28 photos Details
Reviews (3) Make Enquiry
From
$101
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details
Reviews (17) Make Enquiry
From
$1,332
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
12 photos Details
Reviews (4) Make Enquiry
From
$1,705
Per Night
5 Bedrooms, 6 Bathrooms, Sleeps 14
29 photos Details
Reviews (12) Make Enquiry
From
$208
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
19 photos Details
Reviews (6) Make Enquiry
From
$1,172
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 15
24 photos Details
Reviews (3) Make Enquiry
From
$187
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
11 photos Details
Reviews (4) Make Enquiry
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Suitability

  • Wheelchair access (8)
  • Elder access (29)
  • Suitable for children (35)
  • Pet friendly (2)
  • Smoking allowed (0)

Amenities

  • Internet (74)
  • Grill (67)
  • Other outdoor space (59)
  • Parking (51)
  • Washer/Dryer (51)
  • View all amenities
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Kailua Vacation Rentals

Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

A Kailua Vacation

Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

Family-Friendly Kailua

From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.