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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.

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  • Showing 1-50 of 300+
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    Wonderful! 4.9/5
    (32 reviews)
    avg/night
    • Studio
    • 1 BA
    • Sleeps 2
    Apartment #507297vb
    32
    Viewed 53 times in the last 48 hours
      Wonderful! 4.9/5
      (94 reviews)
      avg/night
      • Studio
      • 1 BA
      • Sleeps 3
      Studio #358394vb
      94
      Viewed 25 times in the last 48 hours
        Wonderful! 4.9/5
        (66 reviews)
        avg/night
        • 1 BR
        • 1 BA
        • Sleeps 2
        Cottage #402303vb
        66
        Viewed 16 times in the last 48 hours
          Wonderful! 4.8/5
          (15 reviews)
          avg/night
          • Studio
          • 1 BA
          • Sleeps 2
          Studio #54947vb
          15
          Viewed 29 times in the last 48 hours
            Wonderful! 4.9/5
            (9 reviews)
            avg/night
            • 3 BR
            • 3 BA
            • Sleeps 6
            House #668743vb
            9
            Viewed 25 times in the last 48 hours
              Exceptional! 5.0/5
              (46 reviews)
              avg/night
              • 1 BR
              • 1 BA
              • Sleeps 4
              Cottage #647593vb
              46
              Viewed 30 times in the last 48 hours
                Wonderful! 4.9/5
                (132 reviews)
                avg/night
                • Studio
                • 1 BA
                • Sleeps 4
                Studio #236604vb
                132
                Viewed 23 times in the last 48 hours
                  Wonderful! 4.9/5
                  (52 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 2
                  Cottage #241024
                  52
                  Viewed 30 times in the last 48 hours
                    Excellent! 4.3/5
                    (15 reviews)
                    avg/night
                    • 4 BR
                    • 3 BA
                    • Separate Toilet
                    • Sleeps 10
                    House #798591vb
                    15
                    Viewed 108 times in the last 48 hours
                      Wonderful! 4.8/5
                      (46 reviews)
                      avg/night
                      • 3 BR
                      • 3 BA
                      • Sleeps 6
                      House #279139vb
                      46
                      Viewed 64 times in the last 48 hours
                        Wonderful! 4.8/5
                        (20 reviews)
                        avg/night
                        • 3 BR
                        • 3 BA
                        • Sleeps 6
                        House #266779
                        20
                        Viewed 28 times in the last 48 hours
                          Exceptional! 5.0/5
                          (40 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          House #421527vb
                          40
                          Viewed 76 times in the last 48 hours
                            Exceptional! 5.0/5
                            (6 reviews)
                            avg/night
                            • 5 BR
                            • 4 BA
                            • Separate Toilet
                            • Sleeps 11
                            Villa #712230vb
                            6
                            Viewed 50 times in the last 48 hours
                              avg/night
                              • Studio
                              • 3 BA
                              • Sleeps 7
                              Condo #8034vb
                              4
                              Viewed 114 times in the last 48 hours
                                Wonderful! 4.9/5
                                (31 reviews)
                                avg/night
                                • 6 BR
                                • 7 BA
                                • Separate Toilets
                                • Sleeps 12
                                House #3007443
                                31
                                Viewed 62 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (7 reviews)
                                  avg/night
                                  • 6 BR
                                  • 3 BA
                                  • Sleeps 14
                                  Villa #469879vb
                                  7
                                  Viewed 9 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (42 reviews)
                                    avg/night
                                    • 4 BR
                                    • 3 BA
                                    • Separate Toilet
                                    • Sleeps 10
                                    House #3007439
                                    42
                                    Viewed 55 times in the last 48 hours
                                      Exceptional! 5.0/5
                                      (20 reviews)
                                      avg/night
                                      • 3 BR
                                      • 2 BA
                                      • Separate Toilet
                                      • Sleeps 6
                                      House #246713vb
                                      20
                                        Excellent! 4.6/5
                                        (24 reviews)
                                        avg/night
                                        • 5 BR
                                        • 4 BA
                                        • Sleeps 15
                                        Villa #123014vb
                                        24
                                        Viewed 10 times in the last 48 hours
                                          Exceptional! 5.0/5
                                          (13 reviews)
                                          avg/night
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 12
                                          House #48531vb
                                          13
                                          Viewed 17 times in the last 48 hours
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 6
                                            House #243739vb
                                              avg/night
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 5
                                              Condo #3682048
                                              1 Review
                                              Viewed 14 times in the last 48 hours
                                                Excellent! 4.3/5
                                                (29 reviews)
                                                avg/night
                                                • 6 BR
                                                • 4 BA
                                                • Separate Toilet
                                                • Sleeps 17
                                                House #87052vb
                                                29
                                                Viewed 219 times in the last 48 hours
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  House #841305vb
                                                  1 Review
                                                  Viewed 9 times in the last 48 hours
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    House #793779vb
                                                    Viewed 36 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (13 reviews)
                                                      avg/night
                                                      • 9 BR
                                                      • 5 BA
                                                      • Separate Toilet
                                                      • Sleeps 22
                                                      Villa #818131vb
                                                      13
                                                      Viewed 8 times in the last 48 hours
                                                        • 4 BR
                                                        • 3 BA
                                                        • Sleeps 9
                                                        House #218554
                                                        3
                                                          Excellent! 4.6/5
                                                          (57 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 2
                                                          Studio #936543
                                                          57
                                                          Viewed 45 times in the last 48 hours
                                                            Wonderful! 4.8/5
                                                            (32 reviews)
                                                            avg/night
                                                            • Studio
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Studio #601845vb
                                                            32
                                                            Viewed 66 times in the last 48 hours
                                                              Excellent! 4.7/5
                                                              (12 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Apartment #825251vb
                                                              12
                                                              Viewed 29 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (36 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 2
                                                                Cottage #553479vb
                                                                36
                                                                Viewed 44 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (38 reviews)
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 2
                                                                  Cottage #3686162
                                                                  38
                                                                  Viewed 7 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (77 reviews)
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 2
                                                                    Studio #440853vb
                                                                    77
                                                                    Viewed 46 times in the last 48 hours
                                                                      Exceptional! 5.0/5
                                                                      (30 reviews)
                                                                      avg/night
                                                                      • Studio
                                                                      • 1 BA
                                                                      • Sleeps 5
                                                                      Cottage #776335vb
                                                                      30
                                                                      Viewed 30 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (73 reviews)
                                                                        avg/night
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Separate Toilet
                                                                        • Sleeps 3
                                                                        Apartment #413896vb
                                                                        73
                                                                        Viewed 38 times in the last 48 hours
                                                                          Exceptional! 5.0/5
                                                                          (32 reviews)
                                                                          avg/night
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 2
                                                                          Bungalow #491890vb
                                                                          32
                                                                          Viewed 23 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (76 reviews)
                                                                            avg/night
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 2
                                                                            Cottage #468087vb
                                                                            76
                                                                            Viewed 22 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (20 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              House #749489vb
                                                                              20
                                                                              Viewed 95 times in the last 48 hours
                                                                                Wonderful! 4.8/5
                                                                                (32 reviews)
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 2
                                                                                Studio #558981vb
                                                                                32
                                                                                Viewed 43 times in the last 48 hours
                                                                                  Exceptional! 5.0/5
                                                                                  (35 reviews)
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 3
                                                                                  Cottage #501134vb
                                                                                  35
                                                                                  Viewed 20 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (30 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 5
                                                                                    Apartment #652533vb
                                                                                    30
                                                                                    Viewed 74 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (15 reviews)
                                                                                      avg/night
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 3
                                                                                      Studio #751869vb
                                                                                      15
                                                                                      Viewed 17 times in the last 48 hours
                                                                                        Excellent! 4.7/5
                                                                                        (22 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 3
                                                                                        Apartment #681128vb
                                                                                        22
                                                                                        Viewed 9 times in the last 48 hours
                                                                                          Exceptional! 5.0/5
                                                                                          (15 reviews)
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 3
                                                                                          Cottage #744270vb
                                                                                          15
                                                                                          Viewed 58 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (28 reviews)
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 3
                                                                                            Studio #3008037
                                                                                            28
                                                                                            Viewed 14 times in the last 48 hours
                                                                                              Excellent! 4.6/5
                                                                                              (20 reviews)
                                                                                              avg/night
                                                                                              • 5 BR
                                                                                              • 5 BA
                                                                                              • Sleeps 10
                                                                                              House #596410vb
                                                                                              20
                                                                                              Viewed 33 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (40 reviews)
                                                                                                avg/night
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 5
                                                                                                Cottage #385643vb
                                                                                                40
                                                                                                Viewed 50 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (13 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  House #826558vb
                                                                                                  13
                                                                                                  Viewed 15 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (7 reviews)
                                                                                                    avg/night
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 2
                                                                                                    House #509824vb
                                                                                                    7
                                                                                                    Viewed 15 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (29 reviews)
                                                                                                      avg/night
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 2
                                                                                                      Studio #492562vb
                                                                                                      29
                                                                                                      Viewed 14 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Kailua Holiday Rentals & Homes (300+)