HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled

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.

Favorite
    Viewed 73 times in the last 48 hours
    Excellent! 4.5/5
    (14 reviews)
    avg/night
    14
    Favorite
      Viewed 142 times in the last 48 hours
      Wonderful! 4.9/5
      (10 reviews)
      avg/night
      10
      Favorite
        Viewed 88 times in the last 48 hours
        Wonderful! 4.9/5
        (48 reviews)
        avg/night
        48
        Favorite
          Viewed 33 times in the last 48 hours
          Wonderful! 4.8/5
          (24 reviews)
          avg/night
          24
          Favorite
            Viewed 137 times in the last 48 hours
            Excellent! 4.7/5
            (58 reviews)
            avg/night
            58
            Favorite
              Viewed 70 times in the last 48 hours
              Wonderful! 4.9/5
              (92 reviews)
              avg/night
              92
              Favorite
                Viewed 65 times in the last 48 hours
                Exceptional! 5/5
                (91 reviews)
                avg/night
                91
                Favorite
                  Viewed 81 times in the last 48 hours
                  Excellent! 4.5/5
                  (27 reviews)
                  avg/night
                  27
                  Favorite
                    Viewed 57 times in the last 48 hours
                    Wonderful! 4.9/5
                    (52 reviews)
                    avg/night
                    52
                    Favorite
                      Viewed 49 times in the last 48 hours
                      Wonderful! 4.9/5
                      (48 reviews)
                      avg/night
                      48
                      Favorite
                        Viewed 72 times in the last 48 hours
                        Wonderful! 4.9/5
                        (42 reviews)
                        avg/night
                        42
                        Favorite
                          Viewed 14 times in the last 48 hours
                          Wonderful! 4.9/5
                          (76 reviews)
                          avg/night
                          76
                          Favorite
                            Viewed 66 times in the last 48 hours
                            Wonderful! 4.8/5
                            (30 reviews)
                            avg/night
                            30
                            Favorite
                              Viewed 16 times in the last 48 hours
                              Excellent! 4.7/5
                              (47 reviews)
                              avg/night
                              47
                              Favorite
                                Viewed 36 times in the last 48 hours
                                Wonderful! 4.8/5
                                (52 reviews)
                                avg/night
                                52
                                Favorite
                                  Viewed 24 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (15 reviews)
                                  avg/night
                                  15
                                  Favorite
                                    Viewed 22 times in the last 48 hours
                                    Excellent! 4.6/5
                                    (57 reviews)
                                    avg/night
                                    57
                                    Favorite
                                      Viewed 39 times in the last 48 hours
                                      Exceptional! 5/5
                                      (31 reviews)
                                      avg/night
                                      31
                                      Favorite
                                        Viewed 23 times in the last 48 hours
                                        Excellent! 4.7/5
                                        (36 reviews)
                                        avg/night
                                        36
                                        Favorite
                                          Viewed 38 times in the last 48 hours
                                          Excellent! 4.6/5
                                          (49 reviews)
                                          avg/night
                                          49
                                          Favorite
                                            Viewed 40 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (51 reviews)
                                            avg/night
                                            51
                                            Favorite
                                              Viewed 32 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (92 reviews)
                                              avg/night
                                              92
                                              Favorite
                                                Viewed 549 times in the last 48 hours
                                                Excellent! 4.3/5
                                                (30 reviews)
                                                avg/night
                                                30
                                                Favorite
                                                  Viewed 45 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (43 reviews)
                                                  avg/night
                                                  43
                                                  Favorite
                                                    Viewed 99 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (100 reviews)
                                                    avg/night
                                                    100
                                                    Favorite
                                                      Viewed 37 times in the last 48 hours
                                                      Wonderful! 4.8/5
                                                      (28 reviews)
                                                      avg/night
                                                      28
                                                      Favorite
                                                        Viewed 82 times in the last 48 hours
                                                        Exceptional! 5/5
                                                        (32 reviews)
                                                        avg/night
                                                        32
                                                        Favorite
                                                          Viewed 18 times in the last 48 hours
                                                          Excellent! 4.5/5
                                                          (24 reviews)
                                                          avg/night
                                                          24
                                                          Favorite
                                                            Viewed 36 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (55 reviews)
                                                            avg/night
                                                            55
                                                            Favorite
                                                              Viewed 21 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (39 reviews)
                                                              avg/night
                                                              39
                                                              Favorite
                                                                Viewed 55 times in the last 48 hours
                                                                Excellent! 4.7/5
                                                                (30 reviews)
                                                                avg/night
                                                                30
                                                                Favorite
                                                                  Viewed 50 times in the last 48 hours
                                                                  Excellent! 4.4/5
                                                                  (25 reviews)
                                                                  avg/night
                                                                  25
                                                                  Favorite
                                                                    Viewed 45 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (103 reviews)
                                                                    avg/night
                                                                    103
                                                                    Favorite
                                                                      Viewed 52 times in the last 48 hours
                                                                      Wonderful! 4.8/5
                                                                      (26 reviews)
                                                                      avg/night
                                                                      26
                                                                      Favorite
                                                                        Viewed 34 times in the last 48 hours
                                                                        Wonderful! 4.8/5
                                                                        (30 reviews)
                                                                        avg/night
                                                                        30
                                                                        Favorite
                                                                          Viewed 47 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (16 reviews)
                                                                          avg/night
                                                                          16
                                                                          Favorite
                                                                            Viewed 62 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (74 reviews)
                                                                            avg/night
                                                                            74
                                                                            Favorite
                                                                              Viewed 50 times in the last 48 hours
                                                                              Wonderful! 4.8/5
                                                                              (58 reviews)
                                                                              avg/night
                                                                              58
                                                                              Favorite
                                                                                Viewed 60 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (63 reviews)
                                                                                avg/night
                                                                                63
                                                                                Favorite
                                                                                  Viewed 31 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (88 reviews)
                                                                                  avg/night
                                                                                  88
                                                                                  Favorite
                                                                                    Viewed 17 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (39 reviews)
                                                                                    avg/night
                                                                                    39
                                                                                    Favorite
                                                                                      Viewed 32 times in the last 48 hours
                                                                                      Exceptional! 5/5
                                                                                      (20 reviews)
                                                                                      avg/night
                                                                                      20
                                                                                      Favorite
                                                                                        Viewed 28 times in the last 48 hours
                                                                                        Exceptional! 5/5
                                                                                        (45 reviews)
                                                                                        avg/night
                                                                                        45
                                                                                        Favorite
                                                                                          Viewed 24 times in the last 48 hours
                                                                                          Excellent! 4.6/5
                                                                                          (50 reviews)
                                                                                          avg/night
                                                                                          50
                                                                                          Favorite
                                                                                            Wonderful! 4.9/5
                                                                                            (60 reviews)
                                                                                            avg/night
                                                                                            60
                                                                                            Favorite
                                                                                              Viewed 69 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (70 reviews)
                                                                                              avg/night
                                                                                              70
                                                                                              Favorite
                                                                                                Viewed 58 times in the last 48 hours
                                                                                                Excellent! 4.6/5
                                                                                                (43 reviews)
                                                                                                avg/night
                                                                                                43
                                                                                                Favorite
                                                                                                  Viewed 31 times in the last 48 hours
                                                                                                  Exceptional! 5/5
                                                                                                  (10 reviews)
                                                                                                  avg/night
                                                                                                  10
                                                                                                  Favorite
                                                                                                    Viewed 15 times in the last 48 hours
                                                                                                    Wonderful! 4.8/5
                                                                                                    (35 reviews)
                                                                                                    avg/night
                                                                                                    35
                                                                                                    Favorite
                                                                                                      Viewed 9 times in the last 48 hours
                                                                                                      Exceptional! 5/5
                                                                                                      (49 reviews)
                                                                                                      avg/night
                                                                                                      49

                                                                                                      Kailua Holiday Homes & Cottages (300+)