Vacation Rentals & Apartments in Kailua

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1,457 apartments

(20) Excellent 

    12

    Tropical Kailua Studio on the Water w/Private Pool

    Oahu / Kailua

    Kailua house

    5 4 nights min

    • sleeps 5
    • 4 nights min
    • Beach / lakeside relaxation
    • Nearest beach 0 mi
    • Swimming pool

    Price per night from

    $171

    Price per night from

    $171

    (1) Very Good 

      24

      Kailua Guesthouse with Pool and Views!

      Oahu / Kailua

      Kailua cottage

      2 5 min stay varies

      • 2 bedrooms
      • sleeps 5
      • min stay varies
      • Nearest beach 0.8 mi
      • Swimming pool
      • Child Friendly

      Price per night from

      $487

      Responds fast!
      avg. 1 hour 16 minutes

      Price per night from

      $487

      (2) Excellent 

        33

        Tranquil Tropical Beach Retreat

        Oahu / Kailua

        Kailua house

        2 5 3 nights min

        • 2 bedrooms
        • sleeps 5
        • 3 nights min
        • Swimming pool
        • Child Friendly
        • Air conditioning

        Price per night from

        $343

        Responds fast!
        avg. 3 hours 13 minutes

        Price per night from

        $343

        (1) Excellent 

          18

          Affordable Place on the Best Beach in Hawaii

          Oahu / Kailua

          Kailua house

          1 2 2 nights min

          • 1 bedroom
          • sleeps 2
          • 2 nights min
          • Nearest beach 0 mi
          • Child Friendly

          Price per night from

          $180

          Responds fast!
          avg. 2 hours 36 minutes

          Price per night from

          $180

          (18) Very Good 

            13

            Cozy Cottage 5 Minute Walk to Kailua Beach

            Oahu / Kailua

            Kailua house

            1 4 3 nights min

            • 1 bedroom
            • sleeps 4
            • 3 nights min
            • Beach / lakeside relaxation
            • Child Friendly
            • Air conditioning

            Price per night from

            $125

            Price per night from

            $125

            (8) Excellent 

              32

              Nancy's Kailua Cottage Makai

              Oahu / Kailua

              Kailua cottage

              1 2 30 nights min

              • 1 bedroom
              • sleeps 2
              • 30 nights min
              • Beach / lakeside relaxation
              • Nearest beach 2 mi
              • Child Friendly

              Price per night from

              $92

              Price per night from

              $92

              (5) Excellent 

                35

                Luxurious 4 BR Kailua Home, Air-Conditioning, Short walk to Beach, Pool!

                Oahu / Kailua

                Kailua house

                4 8 2 nights min

                • 4 bedrooms
                • sleeps 8
                • 2 nights min
                • Swimming pool
                • Child Friendly
                • Air conditioning

                Price per night from

                $686

                Responds fast!
                avg. 21 minutes

                Price per night from

                $686

                (7) Excellent 

                Certificate of Excellence

                  14

                  Perfect Oasis, Steps to the Beach! 100% Solar!

                  Oahu / Kailua

                  Kailua cottage

                  1 2 4 nights min

                  • 1 bedroom
                  • sleeps 2
                  • 4 nights min
                  “Great cottage in best part of Kailua” We live in Kauai and periodically come to Oahu to visit friends or to for medical appointments. For a recent 4-night trip, we decided to stay in a vacation rental rather than a hotel; we chose Kailua because the b
                  …see more

                  Certificate of Excellence

                  Price per night from

                  $205

                  Responds fast!
                  avg. 2 hours 55 minutes

                  Price per night from

                  $205

                  (2) Excellent 

                    13

                    Lanikai Cottage

                    Oahu / Kailua

                    Kailua house

                    2 4 min stay varies

                    • 2 bedrooms
                    • sleeps 4
                    • min stay varies
                    • Beach / lakeside relaxation
                    • Nearest beach 0 mi
                    • Child Friendly

                    Price per night from

                    $401

                    Price per night from

                    $401

                    (3) Excellent 

                      15

                      Best Location in Kailua! D&D's Cottage

                      Oahu / Kailua

                      Kailua cottage

                      1 2 min stay varies

                      • 1 bedroom
                      • sleeps 2
                      • min stay varies
                      • Child Friendly

                      Price per night from

                      $124

                      Responds fast!
                      avg. 1 hour 17 minutes

                      Price per night from

                      $124

                      (1) Very Good 

                        12

                        Holiday Palms - Private -5 min from Kailua beach

                        Oahu / Kailua

                        Kailua cottage

                        1 5 1 night min

                        • 1 bedroom
                        • sleeps 5
                        • 1 night min
                        • Beach / lakeside relaxation
                        • Child Friendly
                        • Car not necessary

                        Price per night from

                        $149

                        Responds fast!
                        avg. 2 hours 2 minutes

                        Price per night from

                        $149

                          24

                          NEW! Cozy Kailua Studio w/Access to Pool & Patio!

                          Oahu / Kailua

                          Kailua studio

                          Studio 2 2 nights min

                          • Studio
                          • sleeps 2
                          • 2 nights min
                          • Swimming pool
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $155

                          Responds fast!
                          avg. 33 minutes

                          Price per night from

                          $155

                          (5) Excellent 

                            75

                            42 feet from Kailua Beach. Exceptional Extended family Getaway

                            Oahu / Kailua

                            Kailua house

                            4 8 min stay varies

                            • 4 bedrooms
                            • sleeps 8
                            • min stay varies
                            • Beach / lakeside relaxation
                            • Child Friendly
                            • Private garden
                            “Best Beach Front Home Yet” We've stayed at several beach front homes in Hawaii and California and this one was our favorite. The layout is perfect for families, the view was awesome, and Kailua Beach is one of our favorite beaches. We also loved the
                            …see more

                            Price per night from

                            $1,000

                            Responds fast!
                            avg. 1 hour 9 minutes

                            Price per night from

                            $1,000

                            (5) Very Good 

                              30

                              Plantation Charm in Kailua

                              Oahu / Kailua

                              Kailua bungalow

                              4 7 5 nights min

                              • 4 bedrooms
                              • sleeps 7
                              • 5 nights min
                              • Beach / lakeside relaxation
                              • Swimming pool
                              • Child Friendly

                              Price per night from

                              $487

                              Responds fast!
                              avg. 3 hours 21 minutes

                              Price per night from

                              $487

                              (38) Very Good 

                                15

                                Hale Ohana steps to Kailua Beach

                                Oahu / Kailua

                                Kailua house

                                1 2 3 nights min

                                • 1 bedroom
                                • sleeps 2
                                • 3 nights min
                                • Beach / lakeside relaxation
                                • Nearest beach 0.6 mi
                                • Car not necessary
                                “Amazing holiday place to stay!!!” We have rented Tina's apartment twice now from sydney australia and plan on returning yearly. The location is right across the road from the most beautiful beach in Hawaii. Tina is an amazing host making sure the r
                                …see more

                                Price per night from

                                $161

                                Responds fast!
                                avg. 3 hours 51 minutes

                                Price per night from

                                $161

                                (2) Very Good 

                                  16

                                  ON BEAUTIFUL KAILUA BEACH

                                  Oahu / Kailua

                                  Kailua house

                                  1 2 3 nights min

                                  • 1 bedroom
                                  • sleeps 2
                                  • 3 nights min
                                  • Child Friendly
                                  • Air conditioning
                                  • Private garden

                                  Price per night from

                                  $212

                                  Responds fast!
                                  avg. 2 hours 36 minutes

                                  Price per night from

                                  $212

                                  (6) Excellent 

                                    24

                                    KAILUA DREAMS-PALI, the perfect mix of Beach/Town

                                    Oahu / Kailua

                                    Kailua apartment

                                    1 3 7 nights min

                                    • 1 bedroom
                                    • sleeps 3
                                    • 7 nights min
                                    • Beach / lakeside relaxation
                                    • Nearest beach 0.32 mi
                                    • Air conditioning

                                    Price per night from

                                    $251

                                    Price per night from

                                    $251

                                    (2) Excellent 

                                      17

                                      Tropical Garden Studio - Pool on property

                                      Oahu / Kailua

                                      Kailua house

                                      1 2 min stay varies

                                      • 1 bedroom
                                      • sleeps 2
                                      • min stay varies
                                      • Swimming pool

                                      Price per night from

                                      $111

                                      Responds fast!
                                      avg. 1 hour 17 minutes

                                      Price per night from

                                      $111

                                      (13) Excellent 

                                      Certificate of Excellence

                                        16

                                        Open Air Loft, Steps from beach

                                        Oahu / Kailua

                                        Kailua apartment

                                        1 2 5 nights min

                                        • 1 bedroom
                                        • sleeps 2
                                        • 5 nights min
                                        • Child Friendly
                                        • Air conditioning

                                        Certificate of Excellence

                                        Price per night from

                                        $218

                                        Responds fast!
                                        avg. 3 hours 31 minutes

                                        Price per night from

                                        $218

                                        (5) Excellent 

                                          23

                                          KAILUA DREAMS-MAKAI: NEW, LUXURIOUS AND SPACIOUS

                                          Oahu / Kailua

                                          Kailua apartment

                                          1 2 3 nights min

                                          • 1 bedroom
                                          • sleeps 2
                                          • 3 nights min
                                          • Beach / lakeside relaxation
                                          • Nearest beach 0.6 mi
                                          • Swimming pool

                                          Price per night from

                                          $281

                                          Price per night from

                                          $281

                                          (9) Excellent 

                                            21

                                            Garden of Dreams - swimming pool on property -

                                            Oahu / Kailua

                                            Kailua studio

                                            Studio 2 min stay varies

                                            • Studio
                                            • sleeps 2
                                            • min stay varies
                                            • Swimming pool
                                            • Air conditioning

                                            Price per night from

                                            $97

                                            Responds fast!
                                            avg. 1 hour 17 minutes

                                            Price per night from

                                            $97

                                            (22) Very Good 

                                              22

                                              4 Bedroom/ 2 Bath Unit -5 Min Walk to Kailua Beach

                                              Oahu / Kailua

                                              Kailua house

                                              4 8 5 nights min

                                              • 4 bedrooms
                                              • sleeps 8
                                              • 5 nights min
                                              • Beach / lakeside relaxation
                                              • Child Friendly
                                              • Air conditioning
                                              “Go when want be a householder of HAWAII!!” Parents & kids were enjoyed to stay and we felt we lives in Hawaii. Everything was perfect but one thing we didn't like is blunt knife!!!! Anyway, thanks for Brandyn and her collegues for supporting us to sta
                                              …see more

                                              Price per night from

                                              $325

                                              Price per night from

                                              $325

                                                21

                                                Kaapuni Kainani

                                                Oahu / Kailua

                                                Kailua house

                                                3 8 7 nights min

                                                • 3 bedrooms
                                                • sleeps 8
                                                • 7 nights min
                                                • Beach / lakeside relaxation
                                                • Nearest beach 0 mi
                                                • Child Friendly

                                                Price per night from

                                                $687

                                                Price per night from

                                                $687

                                                  10

                                                  Kailua Beach Wagon

                                                  Oahu / Kailua

                                                  Kailua camper van

                                                  1 2 1 night min

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • 1 night min
                                                  • Child Friendly

                                                  Price per night from

                                                  $132

                                                  Price per night from

                                                  $132

                                                  (1) Excellent 

                                                    12

                                                    Ginger studio, private entry/bathroom, near beach

                                                    Oahu / Kailua

                                                    Kailua studio

                                                    Studio 2 3 nights min

                                                    • Studio
                                                    • sleeps 2
                                                    • 3 nights min
                                                    • Nearest beach 0.3 mi
                                                    • Suitable for children age 5+
                                                    • Air conditioning

                                                    Price per night from

                                                    $103

                                                    Price per night from

                                                    $103

                                                    (2) Very Good 

                                                      25

                                                      Kailua by the Sea Studio

                                                      Oahu / Kailua

                                                      Kailua room

                                                      1 2 3 nights min

                                                      • 1 bedroom
                                                      • sleeps 2
                                                      • 3 nights min
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 0.18 mi
                                                      • Ask about children

                                                      Price per night from

                                                      $197

                                                      Price per night from

                                                      $197

                                                        23

                                                        Lovely 2 Bedrooms Homeaway in Kailua Beach Town

                                                        Oahu / Kailua

                                                        Kailua house

                                                        2 6 1 night min

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • 1 night min
                                                        • Child Friendly
                                                        • Air conditioning
                                                        • Private garden

                                                        Price per night from

                                                        $204

                                                        Price per night from

                                                        $204

                                                        (3) Excellent 

                                                          21

                                                          Hale Luana

                                                          Oahu / Kailua

                                                          Kailua cottage

                                                          1 2 5 nights min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 5 nights min
                                                          • Beach / lakeside relaxation
                                                          • Nearest beach 1 mi
                                                          • Air conditioning

                                                          Price per night from

                                                          $229

                                                          Price per night from

                                                          $229

                                                            15

                                                            Martins Hale

                                                            Oahu / Kailua

                                                            Kailua cottage

                                                            1 3 min stay varies

                                                            • 1 bedroom
                                                            • sleeps 3
                                                            • min stay varies
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $224

                                                            Price per night from

                                                            $224

                                                            (3) Excellent 

                                                              25

                                                              Kailua, Cozy, Spacious Duplex Home

                                                              Oahu / Kailua

                                                              Kailua house

                                                              1 3 min stay varies

                                                              • 1 bedroom
                                                              • sleeps 3
                                                              • min stay varies
                                                              • Child Friendly
                                                              • Air conditioning
                                                              • Private garden

                                                              Price per night from

                                                              $172

                                                              Responds fast!
                                                              avg. 3 hours 47 minutes

                                                              Price per night from

                                                              $172

                                                              (3) Very Good 

                                                                7

                                                                Sheffield Studio Walk to Kailua Beach or Town

                                                                Oahu / Kailua

                                                                Kailua b and b

                                                                2 min stay varies

                                                                • sleeps 2
                                                                • min stay varies
                                                                • Nearest beach 0.16 mi
                                                                • Ask about children
                                                                • Air conditioning

                                                                Price per night from

                                                                $165

                                                                Price per night from

                                                                $165

                                                                  6

                                                                  Nice cozy studio3, Enchanted Lake Kailua

                                                                  Oahu / Kailua

                                                                  Kailua studio

                                                                  Studio 2 2 nights min

                                                                  • Studio
                                                                  • sleeps 2
                                                                  • 2 nights min
                                                                  • Nearest beach 1 mi
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $81

                                                                  Price per night from

                                                                  $81

                                                                  (1) Excellent 

                                                                    10

                                                                    The quaint Kailua-Kalama "Cottage"

                                                                    Oahu / Kailua

                                                                    Kailua cottage

                                                                    2 1 night min

                                                                    • sleeps 2
                                                                    • 1 night min
                                                                    • Car not necessary
                                                                    • Ask about pets
                                                                    • Private garden

                                                                    Price per night from

                                                                    $121

                                                                    Price per night from

                                                                    $121

                                                                      15

                                                                      On Beautiful Kailua Beach

                                                                      Oahu / Kailua

                                                                      Kailua villa

                                                                      1 2 3 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 2
                                                                      • 3 nights min
                                                                      • Nearest beach 0 mi
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $178

                                                                      Responds fast!
                                                                      avg. 2 hours 36 minutes

                                                                      Price per night from

                                                                      $178

                                                                      (4) Excellent 

                                                                        13

                                                                        Beachfront Kailua, Oahu

                                                                        Oahu / Kailua

                                                                        Kailua house

                                                                        2 6 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Beach / lakeside relaxation
                                                                        • Child Friendly
                                                                        • Ask about pets

                                                                        Price per night from

                                                                        $516

                                                                        Price per night from

                                                                        $516

                                                                        (7) Excellent 

                                                                          15

                                                                          Nancy's Kailua Cottage Mauka

                                                                          Oahu / Kailua

                                                                          Kailua cottage

                                                                          4 30 nights min

                                                                          • sleeps 4
                                                                          • 30 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Nearest beach 2 mi
                                                                          • Child Friendly
                                                                          “Nancy's is the perfect place to get away from the hustle of Honolulu!” My wife and I recently stayed at Nancy's while on Oahu. It's a short hop across the island in Kailua, about a 20-30 minute drive from Honolulu. The cottage has everything you need,
                                                                          …see more

                                                                          Price per night from

                                                                          $92

                                                                          Price per night from

                                                                          $92

                                                                            20

                                                                            Shangri La By The Sea

                                                                            Oahu / Kailua

                                                                            Kailua house

                                                                            5 10 min stay varies

                                                                            • 5 bedrooms
                                                                            • sleeps 10
                                                                            • min stay varies
                                                                            • Beach / lakeside relaxation
                                                                            • Swimming pool
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $1,031

                                                                            Price per night from

                                                                            $1,031

                                                                              16

                                                                              Loft in Kailua

                                                                              Oahu / Kailua

                                                                              Kailua house

                                                                              2 2 14 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 2
                                                                              • 14 nights min
                                                                              • Nearest beach 2 mi
                                                                              • Swimming pool
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $258

                                                                              Responds fast!
                                                                              avg. 1 hour 16 minutes

                                                                              Price per night from

                                                                              $258

                                                                              About Kailua

                                                                              Just a quick drive from the capital of Honolulu and Waikiki Beach, the small coastal town of Kailua is one of Hawaii's most picturesque and accessible beach communities. Overlooking the expansive, sapphire blue Kailua Bay, the town is bordered by a gorgeous white sand beach, often ranked among the best in Hawaii. Bring your book, a beach towel, and a pair of flip flops; you don't need much more to enjoy life in Kailua.

                                                                              With continuous trade winds rolling off the coast, the climate is always comfortable in sunny Kailua, Hawaii. Thanks to the steady breeze, it is also a great spot for windsurfing and other beach activities, like horseback riding, swimming, kayaking, and snorkeling. If you want to explore the tropical scenery around Kailua, there are also tons of hiking trails in the surrounding Koolau Ridge and the Ka Iwi Ridge.

                                                                              Here are a few additional suggestions of things to do in Kailua:

                                                                              • Kailua Beach Park: An uninterrupted two-mile stretch of white sand and blue sea, Kailua Beach has been repeatedly named one of Hawaii's best beaches.
                                                                              • Lanikai: Just outside Kailua, the small community of Lanikai is home to another incredibly beautiful stretch of sand.
                                                                              • Honolulu and Waikiki: If you visit Kailua, don't overlook its famous neighbor, the fun capital city of Honolulu.
                                                                              • Ka'iwa Ridge Trail: Spend a few hours ascending the Ka'iwa Ridge for fabulous views of Kailua Bay below.
                                                                              • Kawainui Marsh: Just outside Kailua, Hawaii's largest wetland and freshwater lagoon is a wonderful place to observe unusual birds and vegetation.
                                                                              • Ulupo Heiau State Historic Site: This historic Hawaiian temple was built in the 18th century and is believed to be the former home of several Oahu chiefs.

                                                                              If you are coming to stay on this piece of paradise, look for a comfortable vacation rental for the family or a luxury villa with ocean views for a romantic getaway. You can also find a condo or apartment for rent, often within walking distance of the waves.