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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.

    Exceptional! 5/5
    (81 reviews)
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    • 5 BR
    • 6 BA
    • Sleeps 10
    House #568512vb
    81
    Viewed 75 times in the last 48 hours
      Excellent! 4.7/5
      (22 reviews)
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      • 4 BR
      • 4 BA
      • Sleeps 10
      House #678699vb
      22
      Viewed 64 times in the last 48 hours
        Exceptional! 5/5
        (7 reviews)
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        • 5 BR
        • 5 BA
        • Sleeps 15
        House #911052vb
        7
        Viewed 70 times in the last 48 hours
          Wonderful! 4.8/5
          (52 reviews)
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          • 5 BR
          • 4 BA
          • Sleeps 14
          House #42225vb
          52
          Viewed 65 times in the last 48 hours
            Wonderful! 4.9/5
            (97 reviews)
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            • 3 BR
            • 2 BA
            • Sleeps 7
            House #207816
            97
            Viewed 43 times in the last 48 hours
              Wonderful! 4.8/5
              (54 reviews)
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              • 3 BR
              • 3 BA
              • Sleeps 6
              House #279139vb
              54
              Viewed 62 times in the last 48 hours
                Wonderful! 4.9/5
                (27 reviews)
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                • 4 BR
                • 4 BA
                • Sleeps 8
                House #576430vb
                27
                Viewed 37 times in the last 48 hours
                  Wonderful! 4.9/5
                  (21 reviews)
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                  • 8 BR
                  • 4 BA
                  • Separate Toilet
                  • Sleeps 16
                  House #392179vb
                  21
                  Viewed 72 times in the last 48 hours
                    Excellent! 4.7/5
                    (26 reviews)
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                    • 5 BR
                    • 5 BA
                    • Sleeps 10
                    House #596410vb
                    26
                    Viewed 38 times in the last 48 hours
                      Wonderful! 4.9/5
                      (39 reviews)
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                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      House #660930vb
                      39
                      Viewed 58 times in the last 48 hours
                        Excellent! 4.3/5
                        (21 reviews)
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                        • 4 BR
                        • 3 BA
                        • Separate Toilet
                        • Sleeps 10
                        House #798591vb
                        21
                        Viewed 66 times in the last 48 hours
                          Wonderful! 4.9/5
                          (29 reviews)
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                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          House #749489vb
                          29
                          Viewed 65 times in the last 48 hours
                            Exceptional! 5/5
                            (17 reviews)
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                            • 5 BR
                            • 4 BA
                            • Separate Toilets
                            • Sleeps 12
                            Bungalow #612170vb
                            17
                            Viewed 178 times in the last 48 hours
                              Exceptional! 5/5
                              (6 reviews)
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                              • 3 BR
                              • 3 BA
                              • Sleeps 10
                              House #793493vb
                              6
                              Viewed 28 times in the last 48 hours
                                Wonderful! 4.9/5
                                (11 reviews)
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                                • 4 BR
                                • 4 BA
                                • Sleeps 12
                                House #893052vb
                                11
                                Viewed 103 times in the last 48 hours
                                  Exceptional! 5/5
                                  (45 reviews)
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                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 6
                                  House #421527vb
                                  45
                                  Viewed 25 times in the last 48 hours
                                    Exceptional! 5/5
                                    (47 reviews)
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                                    • 4 BR
                                    • 3 BA
                                    • Separate Toilet
                                    • Sleeps 10
                                    House #3007439
                                    47
                                    Viewed 78 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (33 reviews)
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                                      • 6 BR
                                      • 7 BA
                                      • Separate Toilets
                                      • Sleeps 12
                                      House #3007443
                                      33
                                      Viewed 46 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (4 reviews)
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                                        • Studio
                                        • 1 BA
                                        • Sleeps 4
                                        Studio #236604vb
                                        4
                                        Viewed 46 times in the last 48 hours
                                          Exceptional! 5/5
                                          (12 reviews)
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                                          • 6 BR
                                          • 6 BA
                                          • Separate Toilet
                                          • Sleeps 15
                                          Villa #712230vb
                                          12
                                          Viewed 65 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (7 reviews)
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                                            • 6 BR
                                            • 3 BA
                                            • Sleeps 14
                                            Villa #469879vb
                                            7
                                            Viewed 13 times in the last 48 hours
                                              Exceptional! 5/5
                                              (5 reviews)
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                                              • Studio
                                              • 3 BA
                                              • Sleeps 7
                                              Condo #8034vb
                                              5
                                              Viewed 146 times in the last 48 hours
                                                Excellent! 4.3/5
                                                (29 reviews)
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                                                • 6 BR
                                                • 4 BA
                                                • Separate Toilet
                                                • Sleeps 17
                                                House #87052vb
                                                29
                                                Viewed 336 times in the last 48 hours
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                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  House #243739vb
                                                  Viewed 8 times in the last 48 hours
                                                    Excellent! 4.7/5
                                                    (45 reviews)
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                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    House #439113vb
                                                    45
                                                    Viewed 87 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (40 reviews)
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                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 5
                                                      Apartment #652533vb
                                                      40
                                                      Viewed 64 times in the last 48 hours
                                                        Wonderful! 4.9/5
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                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 8
                                                        House #867153vb
                                                        12
                                                        Viewed 46 times in the last 48 hours
                                                          Excellent! 4.7/5
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                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          Cottage #4070445
                                                          23
                                                          Viewed 47 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (85 reviews)
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                                                            • 1 BR
                                                            • 1 BA
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                                                            Apartment #413896vb
                                                            85
                                                            Viewed 34 times in the last 48 hours
                                                              Excellent! 4.5/5
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                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 10
                                                              House #5151vb
                                                              29
                                                              Viewed 100 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (24 reviews)
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                                                                • 3 BR
                                                                • 3 BA
                                                                • Sleeps 6
                                                                House #266779
                                                                24
                                                                Viewed 21 times in the last 48 hours
                                                                  Exceptional! 5/5
                                                                  (63 reviews)
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                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  House #269885vb
                                                                  63
                                                                  Viewed 29 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (23 reviews)
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                                                                    • Studio
                                                                    • 1 BA
                                                                    • Sleeps 3
                                                                    Cottage #779846vb
                                                                    23
                                                                    Viewed 17 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (8 reviews)
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                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      House #916730vb
                                                                      8
                                                                      Viewed 107 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (52 reviews)
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                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Separate Toilet
                                                                        • Sleeps 6
                                                                        House #71019vb
                                                                        52
                                                                        Viewed 54 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (45 reviews)
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                                                                          • 3 BR
                                                                          • 4 BA
                                                                          • Sleeps 10
                                                                          House #2407vb
                                                                          45
                                                                          Viewed 53 times in the last 48 hours
                                                                            Very Good! 4.2/5
                                                                            (5 reviews)
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                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            House #202762vb
                                                                            5
                                                                            Viewed 13 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (71 reviews)
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                                                                              • Studio
                                                                              • 1 BA
                                                                              • Sleeps 3
                                                                              Studio #68420vb
                                                                              71
                                                                              Viewed 79 times in the last 48 hours
                                                                                Wonderful! 4.8/5
                                                                                (39 reviews)
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                                                                                • Studio
                                                                                • 1 BA
                                                                                • Sleeps 2
                                                                                Apartment #507297vb
                                                                                39
                                                                                Viewed 27 times in the last 48 hours
                                                                                  Excellent! 4.7/5
                                                                                  (45 reviews)
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                                                                                  • Studio
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  Studio #601845vb
                                                                                  45
                                                                                  Viewed 58 times in the last 48 hours
                                                                                    Exceptional! 5/5
                                                                                    (17 reviews)
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                                                                                    • 4 BR
                                                                                    • 4 BA
                                                                                    • Sleeps 12
                                                                                    Estate #58901vb
                                                                                    17
                                                                                    Viewed 36 times in the last 48 hours
                                                                                      Excellent! 4.5/5
                                                                                      (22 reviews)
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                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 4
                                                                                      Cottage #557396vb
                                                                                      22
                                                                                      Viewed 41 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (49 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 10
                                                                                        House #65043vb
                                                                                        49
                                                                                        Viewed 84 times in the last 48 hours
                                                                                          Excellent! 4.7/5
                                                                                          (65 reviews)
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 2
                                                                                          Studio #936543
                                                                                          65
                                                                                          Viewed 40 times in the last 48 hours
                                                                                            Exceptional! 5/5
                                                                                            (26 reviews)
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            Cottage #4055919
                                                                                            26
                                                                                            Viewed 36 times in the last 48 hours
                                                                                              Exceptional! 5/5
                                                                                              (49 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              House #171995
                                                                                              49
                                                                                              Viewed 39 times in the last 48 hours
                                                                                                Excellent! 4.7/5
                                                                                                (59 reviews)
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                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 5
                                                                                                House #29472vb
                                                                                                59
                                                                                                Viewed 26 times in the last 48 hours
                                                                                                  Excellent! 4.6/5
                                                                                                  (46 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  House #76037vb
                                                                                                  46
                                                                                                  Viewed 47 times in the last 48 hours
                                                                                                    Excellent! 4.6/5
                                                                                                    (52 reviews)
                                                                                                    avg/night
                                                                                                    • Studio
                                                                                                    • 1 BA
                                                                                                    • Sleeps 2
                                                                                                    Studio #7798vb
                                                                                                    52
                                                                                                    Viewed 38 times in the last 48 hours
                                                                                                      Wonderful! 4.8/5
                                                                                                      (33 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 6
                                                                                                      House #472609vb
                                                                                                      33
                                                                                                      Viewed 14 times in the last 48 hours
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                                                                                                      Kailua Holiday Rentals & Homes (300+)