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Make a holiday rental beach house or self-catering holiday home in Kailua, Hawaii your home away from home

The small beach town of Kailua is located on the beautiful windward side of Hawaii’s Oahu Island. The Koolau Mountains create a stunning backdrop to the town, which stretches along some of the most beautiful beaches in Hawaii. From white sandy beaches and tall volcanic peaks to lush tropical forests, Kailua holidays are the perfect solution for visitors looking for luxury, tranquility and good surfing.

Things to do on holiday in Kailua, Hawaii, USA

The beautiful sandy Kailua beach has consistently been voted one of the best beaches in the world and it’s easy to understand why. The soft white sandy beach is perfect for a walk in the morning, and the clear blue waters are ideal for surfing. Located on the windward side of Oahu, Kailua beach has perfect windsurfing conditions. Other water sports in the area include snorkeling, scuba diving, sailing, jet skiing and parasailing. If you’re feeling adventurous you can rent a kayak and explore the 3 deserted islands located just off the Kailua coast.

The Koolau Mountains that surround Kailua are perfect for hiking. The lush tropical vegetation that covers the mountainside is punctuated by dozens of picturesque waterfalls.

There are 6 world-class golf courses within 10 miles of Kailua villas. After a day on the golf course visitors can enjoy typical Hawaiian cuisine at a Kailua restaurant. A cross between east and west, Hawaiian cuisine includes dishes such as poi, Kalua pig and laulau, and of course, fresh fish.

Places to visit on holiday in Kailua, Hawaii, USA

No visit to Oahu would be complete without a trip to the world’s most famous surfing beach – the Pipeline on the North Shore, which hosts some of the biggest surfing competitions in the world. Even if you don’t plan to surf, just watching the spectacular 30ft waves make it worth the trip.

The bustling cities of Waikiki and Honolulu are both within an hour’s driving distance of beach cottages in Kailua. Both cities are excellent spots for shopping and have vibrant nightlife to suit a variety of tastes.

Another must-see on Oahu is the historic town of Pearl Harbor. Here visitors can see the USS Arizona Memorial that marks the resting place of sailors who lost their lives in the 1941 attack on Pearl Harbor.

Weather in Kailua, Hawaii, USA

The island of Oahu is blessed with warm, sunny weather throughout the year. Temperatures in the middle of winter can reach as high as 27°C. Kailua is located on the windward side of the island, which frequently has afternoon showers.

Flights to Kailua, Hawaii, USA

Reaching Kailua accommodation has never been easier. Honolulu International Airport (HNL) is 14 miles away from beach houses in Kailua. There are no direct flights from the UK to Hawaii, however British Airways offers flights from London to Honolulu via Los Angeles. It is recommended that visitors to Oahu rent a car and drive to their Kailua accommodation.

Wonderful! 4.9/5
(47 reviews)
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  • 1 BA
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Apartment #507297vb
47
Viewed 92 times in the last 48 hours
Wonderful! 4.9/5
(10 reviews)
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  • 3 BR
  • 2 BA
  • Sleeps 6
House #916730vb
10
Viewed 179 times in the last 48 hours
Wonderful! 4.9/5
(46 reviews)
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  • 2 BR
  • 1 BA
  • Sleeps 5
Apartment #652533vb
46
Viewed 80 times in the last 48 hours
Excellent! 4.7/5
(54 reviews)
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  • 3 BR
  • 2 BA
  • Sleeps 6
House #439113vb
54
Viewed 181 times in the last 48 hours
Wonderful! 4.8/5
(28 reviews)
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  • 4 BR
  • 4 BA
  • Sleeps 10
House #678699vb
28
Viewed 190 times in the last 48 hours
Exceptional! 5/5
(89 reviews)
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  • 5 BR
  • 6 BA
  • Sleeps 10
House #568512vb
89
Viewed 67 times in the last 48 hours
Wonderful! 4.9/5
(52 reviews)
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  • 4 BR
  • 3 BA
  • Sleeps 10
House #65043vb
52
Viewed 116 times in the last 48 hours
Wonderful! 4.9/5
(76 reviews)
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  • 1 BR
  • 1 BA
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Cottage #402303vb
76
Viewed 39 times in the last 48 hours
Wonderful! 4.9/5
(41 reviews)
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  • 3 BR
  • 2 BA
  • Sleeps 6
House #749489vb
41
Viewed 100 times in the last 48 hours
Wonderful! 4.8/5
(23 reviews)
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  • 2 BR
  • 1 BA
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House #752838vb
23
Viewed 25 times in the last 48 hours
Wonderful! 4.9/5
(91 reviews)
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  • 1 BA
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Cottage #468087vb
91
Viewed 47 times in the last 48 hours
Excellent! 4.6/5
(56 reviews)
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  • 1 BA
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Studio #7798vb
56
Viewed 45 times in the last 48 hours
Wonderful! 4.9/5
(48 reviews)
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  • 1 BR
  • 1 BA
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House #272975vb
48
Viewed 35 times in the last 48 hours
Wonderful! 4.8/5
(49 reviews)
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  • Studio
  • 1 BA
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Studio #601845vb
49
Viewed 75 times in the last 48 hours
Wonderful! 4.8/5
(28 reviews)
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  • 2 BR
  • 1 BA
  • Sleeps 6
Cottage #4070445
28
Viewed 49 times in the last 48 hours
Exceptional! 5/5
(30 reviews)
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  • 1 BR
  • 1 BA
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Studio #494397vb
30
Viewed 21 times in the last 48 hours
Exceptional! 5/5
(30 reviews)
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  • 1 BR
  • 1 BA
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Cottage #4055919
30
Viewed 24 times in the last 48 hours
Excellent! 4.5/5
(25 reviews)
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  • 4 BR
  • 3 BA
  • Separate Toilet
  • Sleeps 10
House #798591vb
25
Viewed 103 times in the last 48 hours
Wonderful! 4.8/5
(98 reviews)
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  • 1 BR
  • 1 BA
  • Sleeps 2
Studio #440853vb
98
Viewed 74 times in the last 48 hours
Wonderful! 4.9/5
(28 reviews)
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  • 4 BR
  • 4 BA
  • Sleeps 8
House #576430vb
28
Viewed 67 times in the last 48 hours
Exceptional! 5/5
(51 reviews)
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  • 4 BR
  • 3 BA
  • Separate Toilet
  • Sleeps 10
House #3007439
51
Viewed 89 times in the last 48 hours
Wonderful! 4.9/5
(39 reviews)
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  • 6 BR
  • 7 BA
  • Separate Toilets
  • Sleeps 12
House #3007443
39
Viewed 107 times in the last 48 hours
Excellent! 4.3/5
(30 reviews)
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  • 6 BR
  • 4 BA
  • Separate Toilet
  • Sleeps 17
House #87052vb
30
Viewed 570 times in the last 48 hours
Excellent! 4.7/5
(35 reviews)
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  • 1 BR
  • 1 BA
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Apartment #660931vb
35
Viewed 18 times in the last 48 hours
Excellent! 4.5/5
(23 reviews)
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  • 1 BR
  • 1 BA
  • Sleeps 3
Cottage #193809vb
23
Viewed 23 times in the last 48 hours
Excellent! 4.6/5
(46 reviews)
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  • Studio
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Studio #264289vb
46
Viewed 36 times in the last 48 hours
Wonderful! 4.8/5
(28 reviews)
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  • 1 BR
  • 1 BA
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Cabin #622946vb
28
Viewed 18 times in the last 48 hours
Wonderful! 4.8/5
(26 reviews)
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  • 3 BR
  • 3 BA
  • Sleeps 6
House #266779
26
Viewed 93 times in the last 48 hours
Wonderful! 4.9/5
(89 reviews)
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  • 1 BR
  • 1 BA
  • Separate Toilet
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Apartment #413896vb
89
Viewed 25 times in the last 48 hours
Wonderful! 4.8/5
(60 reviews)
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  • 2 BR
  • 1 BA
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House #29472vb
60
Viewed 19 times in the last 48 hours
Excellent! 4.4/5
(25 reviews)
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  • 2 BR
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Cottage #557396vb
25
Viewed 92 times in the last 48 hours
Wonderful! 4.9/5
(88 reviews)
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  • 1 BR
  • 1 BA
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House #7848vb
88
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Wonderful! 4.8/5
(15 reviews)
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Studio #651002vb
15
Viewed 24 times in the last 48 hours
Wonderful! 4.8/5
(57 reviews)
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House #279139vb
57
Viewed 90 times in the last 48 hours
Wonderful! 4.9/5
(42 reviews)
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  • 2 BA
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House #660930vb
42
Viewed 56 times in the last 48 hours
Excellent! 4.7/5
(47 reviews)
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  • 1 BR
  • 1 BA
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Apartment #48730vb
47
Viewed 5 times in the last 48 hours
Wonderful! 4.9/5
(73 reviews)
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Studio #68420vb
73
Viewed 71 times in the last 48 hours
Wonderful! 4.9/5
(102 reviews)
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  • 3 BR
  • 2 BA
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House #207816
102
Viewed 62 times in the last 48 hours
Wonderful! 4.9/5
(60 reviews)
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  • 1 BR
  • 1 BA
  • Sleeps 2
Cottage #241024
60
Viewed 8 times in the last 48 hours
Wonderful! 4.9/5
(14 reviews)
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  • 4 BR
  • 4 BA
  • Sleeps 12
House #893052vb
14
Viewed 58 times in the last 48 hours
Exceptional! 5/5
(26 reviews)
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Studio #751869vb
26
Viewed 17 times in the last 48 hours
Wonderful! 4.9/5
(55 reviews)
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  • 3 BR
  • 2 BA
  • Separate Toilet
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House #71019vb
55
Viewed 43 times in the last 48 hours
Wonderful! 4.9/5
(44 reviews)
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  • 1 BR
  • 1 BA
  • Sleeps 2
House #769616vb
44
Viewed 39 times in the last 48 hours
Excellent! 4.6/5
(42 reviews)
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  • 3 BR
  • 1 BA
  • Separate Toilet
  • Sleeps 6
House #475386vb
42
Viewed 42 times in the last 48 hours
Wonderful! 4.8/5
(33 reviews)
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  • 1 BR
  • 1 BA
  • Sleeps 2
Cottage #7522vb
33
Viewed 23 times in the last 48 hours
Wonderful! 4.9/5
(38 reviews)
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  • 1 BR
  • 1 BA
  • Sleeps 3
Cottage #55009vb
38
Viewed 8 times in the last 48 hours
Wonderful! 4.9/5
(53 reviews)
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  • 1 BR
  • 1 BA
  • Sleeps 2
Cottage #3686162
53
Viewed 45 times in the last 48 hours
Exceptional! 5/5
(56 reviews)
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  • 1 BR
  • 1 BA
  • Sleeps 4
Cottage #647593vb
56
Viewed 34 times in the last 48 hours
Excellent! 4.6/5
(50 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
House #76037vb
50
Viewed 51 times in the last 48 hours
Wonderful! 4.9/5
(15 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 8
House #867153vb
15
Viewed 63 times in the last 48 hours

Kailua Holiday Rentals & Homes (300+)