Vacation Rentals with Pool in Island of Hawaii

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Filtering by: Swimming pool

1,011 vacation rentals

(11) Excellent 

    19

    Ocean Front Kona Makai Perfect Sunset Views Furnished 1 bedroom Condo

    Island of Hawaii / Kailua-Kona

    Kailua-Kona condo

    1 4 min stay varies

    • 1 bedroom
    • sleeps 4
    • min stay varies
    • Beach / lakeside relaxation
    • Nearest beach 2 mi
    • Swimming pool
    “Execellent and affordable place to stay in Kona.” We have stayed here five times in past seven years. It is definitely our favorite place to stay in Kona. We have visited every Hawaiian island except Lanai. The Big Island is our favorite and the Kona
    …see more

    Price per night from

    $105

    Responds fast!
    avg. 1 hour 43 minutes

    Price per night from

    $105

    (3) Excellent 

      41

      Ono Hale: Gorgeous Home with pool. Breathtaking ocean views.

      Island of Hawaii / Kailua-Kona

      Kailua-Kona house

      3 8 min stay varies

      • 3 bedrooms
      • sleeps 8
      • min stay varies
      • Swimming pool
      • Child Friendly

      Price per night from

      $300

      Price per night from

      $300

      (1) Excellent 

        22

        VISTA WAIKOLOA #E105 - Ground floor, upgraded 2/2 - 5th Night Free Special!

        Kohala Coast / Waikoloa

        Waikoloa apartment

        2 5 min stay varies

        • 2 bedrooms
        • sleeps 5
        • min stay varies
        • Swimming pool
        • Child Friendly
        • Air conditioning
        “Vista Wikolia” Great pool for lap swimming. Condo was renovated which made a big difference
        …see more

        Price per night from

        $139

        Responds fast!
        avg. 5 minutes

        Price per night from

        $139

        (1) Excellent 

          33

          KKSR#5104 DIRECT OCEANFRONT, BEST GROUND FLOOR CORNER! REMODELED! AC!!!!

          Island of Hawaii / Kailua-Kona

          Kailua-Kona apartment

          2 4 min stay varies

          • 2 bedrooms
          • sleeps 4
          • min stay varies
          • Swimming pool
          • Ask about children
          • Air conditioning
          “Great location” We loved the location, clean , beds comfortable, views were wonderful! We were worried there was no air conditioner but we didn't need it.
          …see more

          Price per night from

          $194

          Price per night from

          $194

          (37) Very Good 

            46

            Sunsets & Surfers - Kona Reef Ocean Front Unit

            Island of Hawaii / Kailua-Kona

            Kailua-Kona apartment

            1 4 min stay varies

            • 1 bedroom
            • sleeps 4
            • min stay varies
            • Beach / lakeside relaxation
            • Nearest beach 0 mi
            • Swimming pool
            “great location and views” awesome location, views, and accommodations. book early because from that calendar on the owners link it fills up fast. just an fyi when you arrive there is underground parking that i have noticed people don't realize. as in
            …see more

            Price per night from

            $159

            Responds fast!
            avg. 1 hour 17 minutes

            Price per night from

            $159

            (1) Excellent 

              10

              Keauhou Gardens 11-303 1Br Ocean v. NO BOOKING FEE

              Island of Hawaii / Kailua-Kona

              Kailua-Kona apartment

              1 2 min stay varies

              • 1 bedroom
              • sleeps 2
              • min stay varies
              • Swimming pool
              • Child Friendly
              • Air conditioning

              Price per night from

              $130

              Price per night from

              $130

              (5) Very Good 

                23

                One Bedroom Condo with Amazing Ocean Views, AC incl.

                Island of Hawaii / Kailua-Kona

                Kailua-Kona apartment

                1 2 min stay varies

                • 1 bedroom
                • sleeps 2
                • min stay varies
                • Swimming pool
                • Ask about children
                • Air conditioning
                “A great vacation” Enjoyed our stay at the Casa de Emdeko and in particular in 337. The unit was spacious, fully equipped and close to the ocean. The pools, barbques and cabana area are handy and perfect for a vacation. I would recommend this location
                …see more

                Price per night from

                $120

                Responds fast!
                avg. 4 minutes

                Price per night from

                $120

                (45) Excellent 

                  25

                  306-AirCon. Upgraded Corner Unit w/Expansive Ocean Views and Extra Large Lanai.

                  Island of Hawaii / Kailua-Kona

                  Kailua-Kona apartment

                  2 6 min stay varies

                  • 2 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Swimming pool
                  • Child Friendly
                  “Trip to Paradise” The condo was amazing, no expense was spared. Great beds, furniture, cookware, everything. We watched surfers from the lanai nearly every day, and the sunsets were the most spectacular we've ever seen. A car is needed for this locati
                  …see more

                  Price per night from

                  $225

                  Responds fast!
                  avg. 51 minutes

                  Price per night from

                  $225

                  (34) Very Good 

                    18

                    2 bdrm 2 ba condo across from White Sands Beach

                    Island of Hawaii / Kailua-Kona

                    Kailua-Kona apartment

                    2 4 4 nights min

                    • 2 bedrooms
                    • sleeps 4
                    • 4 nights min
                    • Beach / lakeside relaxation
                    • Nearest beach 0.05 mi
                    • Swimming pool
                    “Beautiful Paradise” This immaculate well maintained condo came equipped with everything needed to snorkel, body board, picnic or just rest by the ocean. The view from the balcony was breathtaking. The condo grounds, pool area, hot tub and barbecue wer
                    …see more

                    Price per night from

                    $150

                    Price per night from

                    $150

                    (6) Excellent 

                    Certificate of Excellence

                      12

                      Wyndham Kona Hawaiian Resort (2 bedroom condo)

                      Island of Hawaii / Kailua-Kona

                      Kailua-Kona condo

                      2 6 min stay varies

                      • 2 bedrooms
                      • sleeps 6
                      • min stay varies
                      • Nearest beach 2 mi
                      • Swimming pool
                      • Child Friendly

                      Certificate of Excellence

                      Price per night from

                      $217

                      Price per night from

                      $217

                        24

                        1 bedroom condo in Oceanfront complex, amazing Ocean views

                        Island of Hawaii / Kailua-Kona

                        Kailua-Kona apartment

                        1 4 min stay varies

                        • 1 bedroom
                        • sleeps 4
                        • min stay varies
                        • Swimming pool
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $120

                        Responds fast!
                        avg. 4 minutes

                        Price per night from

                        $120

                          24

                          Beautiful 3BR / 3BA home with ocean views & pool - Check out our Virtual Tour

                          Island of Hawaii / Kailua-Kona

                          Kailua-Kona house

                          3 8 min stay varies

                          • 3 bedrooms
                          • sleeps 8
                          • min stay varies
                          • Swimming pool
                          • Ask about children

                          Price per night from

                          $289

                          Price per night from

                          $289

                          (8) Very Good 

                            14

                            SEA VILLAGE RESORT in Kona (Oceanfront/Oceanview)

                            Island of Hawaii / Kailua-Kona

                            Kailua-Kona apartment

                            2 6 1 night min

                            • 2 bedrooms
                            • sleeps 6
                            • 1 night min
                            • Beach / lakeside relaxation
                            • Swimming pool
                            • Child Friendly
                            “Excellent!” We had a great time at the Sea Village and Rick was very helpful. A very nice condo in right at the sea. Highly recommended!
                            …see more

                            Price per night from

                            $181

                            Responds fast!
                            avg. 3 hours 30 minutes

                            Price per night from

                            $181

                            (1) Excellent 

                              21

                              Stylish Shores Retreat with Garden Views

                              Kohala Coast / Waikoloa

                              Waikoloa apartment

                              2 4 4 nights min

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

                              Price per night from

                              $165

                              Price per night from

                              $165

                              (25) Very Good 

                                25

                                Beautiful Condo Just Steps from Rare Sandy Beach

                                Island of Hawaii / Kailua-Kona

                                Kailua-Kona apartment

                                1 2 min stay varies

                                • 1 bedroom
                                • sleeps 2
                                • min stay varies
                                • Beach / lakeside relaxation
                                • Swimming pool
                                • Air conditioning
                                “Wonderful Condo in the Heart of Kailua-Kona” My fiancee and I really enjoyed staying at this condo. It was quite nice inside with a great kitchen, living room, bathroom, king bed in the bedroom, and a lovely lanai overlooking the pool and ocean. Per
                                …see more

                                Price per night from

                                $159

                                Responds fast!
                                avg. 2 hours 7 minutes

                                Price per night from

                                $159

                                  21

                                  Oceanfront-Incredible Views, Surf Break & Romantic Sunsets at Bali Kai 223

                                  Island of Hawaii / Kailua-Kona

                                  Kailua-Kona apartment

                                  2 6 min stay varies

                                  • 2 bedrooms
                                  • sleeps 6
                                  • min stay varies
                                  • Swimming pool
                                  • Ask about children

                                  Price per night from

                                  $149

                                  Price per night from

                                  $149

                                    19

                                    Charming Top Floor Condo with Mountain Views

                                    Kohala Coast / Waikoloa

                                    Waikoloa apartment

                                    2 4 4 nights min

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

                                    Price per night from

                                    $155

                                    Price per night from

                                    $155

                                    (2) Very Good 

                                      12

                                      Surf & Racquet Club 5102 2/2 ocean NO BOOKING FEE

                                      Island of Hawaii / Kailua-Kona

                                      Kailua-Kona apartment

                                      2 4 min stay varies

                                      • 2 bedrooms
                                      • sleeps 4
                                      • min stay varies
                                      • Beach / lakeside relaxation
                                      • Swimming pool
                                      • Child Friendly

                                      Price per night from

                                      $210

                                      Price per night from

                                      $210

                                        21

                                        Kona Plaza#402 TOP FLOOR OCEAN VIEW IN HEART OF KONA TOWN! AC & Elevators!

                                        Island of Hawaii / Kailua-Kona

                                        Kailua-Kona condo

                                        1 2 min stay varies

                                        • 1 bedroom
                                        • sleeps 2
                                        • min stay varies
                                        • Swimming pool
                                        • Ask about children
                                        • Air conditioning

                                        Price per night from

                                        $99

                                        Price per night from

                                        $99

                                        (1) Very Good 

                                          31

                                          ***2 bedroom 2 bath condo, Free A/C, shared infinity pool, walk to beach***

                                          Island of Hawaii / Kailua-Kona

                                          Kailua-Kona condo

                                          2 4 min stay varies

                                          • 2 bedrooms
                                          • sleeps 4
                                          • min stay varies
                                          • Swimming pool
                                          • Ask about children
                                          • Air conditioning

                                          Price per night from

                                          $240

                                          Responds fast!
                                          avg. 4 minutes

                                          Price per night from

                                          $240

                                          (41) Average 

                                            27

                                            Ocean front condo next to Reeds Bay in Hilo, HI

                                            Island of Hawaii / Hilo

                                            Hilo apartment

                                            1 4 2 nights min

                                            • 1 bedroom
                                            • sleeps 4
                                            • 2 nights min
                                            • Beach / lakeside relaxation
                                            • Swimming pool
                                            • Child Friendly
                                            “Cozy, comfortable and just right!” This Banyan Drive location and condo were perfect for what we wanted. We loved the view and the proximity to the water. Shops, restaurants, and recreational rentals were right around the corner. Old Town Hilo was a
                                            …see more

                                            Price per night from

                                            $86

                                            Responds fast!
                                            avg. 2 hours 45 minutes

                                            Price per night from

                                            $86

                                            (20) Excellent 

                                              24

                                              Punaluu Black Sand Beach, Big Island, Hawaii

                                              Island of Hawaii / Pahala

                                              Pahala apartment

                                              1 4 min stay varies

                                              • 1 bedroom
                                              • sleeps 4
                                              • min stay varies
                                              • Beach / lakeside relaxation
                                              • Nearest beach 0.5 mi
                                              • Swimming pool
                                              “Holiday on the Big Island” We loved our stay at Punalu Black Sand Beach condos and Jeff our host was very polite and professional in sending us via email all required info to make our stay enjoyable. The cottage is beautiful, perfect for 3 guests with
                                              …see more

                                              Price per night from

                                              $132

                                              Responds fast!
                                              avg. 3 hours 21 minutes

                                              Price per night from

                                              $132

                                                19

                                                Waikoloa Villas #H-104

                                                Kohala Coast / Waikoloa

                                                Waikoloa villa

                                                1 4 min stay varies

                                                • 1 bedroom
                                                • sleeps 4
                                                • min stay varies
                                                • Swimming pool
                                                • Car not necessary

                                                Price per night from

                                                $154

                                                Price per night from

                                                $154

                                                  24

                                                  'The Park House' Kapaau Home w/Patio-2 Mi to Beach

                                                  Island of Hawaii / Kapaau

                                                  Kapaau house

                                                  3 5 4 nights min

                                                  • 3 bedrooms
                                                  • sleeps 5
                                                  • 4 nights min
                                                  • Swimming pool
                                                  • Child Friendly

                                                  Price per night from

                                                  $201

                                                  Responds fast!
                                                  avg. 11 minutes

                                                  Price per night from

                                                  $201

                                                  (4) Excellent 

                                                    10

                                                    Wyndham Kona Hawaiian Resort (2 bedroom condo)

                                                    Island of Hawaii / Kailua-Kona

                                                    Kailua-Kona condo

                                                    2 6 min stay varies

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • min stay varies
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Air conditioning
                                                    “We loved our stay here” This was a great location for exploring hawai'i island, and was great for 2 couples. It was quiet, all the staff was very nice, and the unit was very enjoyable, with a nice large lanai . I'm happy we picked here to stay.
                                                    …see more

                                                    Price per night from

                                                    $205

                                                    Price per night from

                                                    $205

                                                    (18) Very Good 

                                                    Certificate of Excellence

                                                      11

                                                      Wyndham Kona Hawaiian Resort (2 bedroom condo)

                                                      Island of Hawaii / Kailua-Kona

                                                      Kailua-Kona condo

                                                      2 6 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 6
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Certificate of Excellence

                                                      Price per night from

                                                      $205

                                                      Price per night from

                                                      $205

                                                      (14) Excellent 

                                                        25

                                                        Oceanfront Beach House w/ Pool and Spa!

                                                        Island of Hawaii / Pahoa

                                                        Pahoa house

                                                        1 2 3 nights min

                                                        • 1 bedroom
                                                        • sleeps 2
                                                        • 3 nights min
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 2 mi
                                                        • Swimming pool
                                                        “Great house with a wonderful view!” We were making out third trip to the Big Island and decided to see another part of the island other than the Kona resort area. The beach house is located in Highway 137 which provides some the most gorgeous scenery
                                                        …see more

                                                        Price per night from

                                                        $401

                                                        Responds fast!
                                                        avg. 2 hours 41 minutes

                                                        Price per night from

                                                        $401

                                                        (37) Very Good 

                                                        Certificate of Excellence

                                                          12

                                                          Wyndham Kona Hawaiian Resort

                                                          Island of Hawaii / Kailua-Kona

                                                          Kailua-Kona condo

                                                          2 6 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Nearest beach 2 mi
                                                          • Swimming pool
                                                          • Child Friendly

                                                          Certificate of Excellence

                                                          Price per night from

                                                          $205

                                                          Price per night from

                                                          $205

                                                          (14) Very Good 

                                                            28

                                                            KKSR#3 DIRECT OCEANFRONT TOWNHOME! Walk to the Beach! Superb Location!

                                                            Island of Hawaii / Keauhou

                                                            Keauhou house

                                                            2 4 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 4
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Ask about children
                                                            “Kona townhouse” Great location...just need a little more of supply esp dish soap...otherwise the place is great...well supplied...Enjoyed the visit and the stay. It needs to have a big recycle bin next the trash bin...the only recycle bin we found is
                                                            …see more

                                                            Price per night from

                                                            $141

                                                            Price per night from

                                                            $141

                                                            (9) Excellent 

                                                              47

                                                              Hawaiian 4 bedroom Ocean Retreat

                                                              Island of Hawaii / Keaau

                                                              Keaau apartment

                                                              4 8 min stay varies

                                                              • 4 bedrooms
                                                              • sleeps 8
                                                              • min stay varies
                                                              • Beach / lakeside relaxation
                                                              • Swimming pool
                                                              • Car not necessary
                                                              “the most relaxing 10 days!” Our stay at the paradise ocean retreat was the most relaxing 10 days I've had in the last 10 years. I was so happy to get a good night's sleep every night except for the first (jet lag.) Being there took away all the stre
                                                              …see more

                                                              Price per night from

                                                              $464

                                                              Price per night from

                                                              $464

                                                              (11) Excellent 

                                                                18

                                                                House of Love by the Sea/ Oceanfront & Salt Pool

                                                                Island of Hawaii / Keaau

                                                                Keaau house

                                                                5 8 3 nights min

                                                                • 5 bedrooms
                                                                • sleeps 8
                                                                • 3 nights min
                                                                • Nearest beach 25 mi
                                                                • Swimming pool
                                                                • Child Friendly
                                                                “I never want to leave!!!” Every morning I"d wake up and sit on the cliff watching the waves crash against the rocks. Sometimes I'd see a turtle. Then I'd go for a swim in the pool before joining my family for our day's adventure. The peace and beau
                                                                …see more

                                                                Price per night from

                                                                $229

                                                                Responds fast!
                                                                avg. 45 minutes

                                                                Price per night from

                                                                $229

                                                                (5) Excellent 

                                                                  21

                                                                  Kona Isle A4 Beautifully appointed condo. Ground Floor, Wifi, AC!

                                                                  Island of Hawaii / Kailua-Kona

                                                                  Kailua-Kona apartment

                                                                  1 4 min stay varies

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Ask about children
                                                                  “Stay” We enjoyed our stay. The place was well equipped and had a nice Hawaian vibe. We have stayed at Kona Isle for many years and we enjoyed A4 very much. Thank you. Dodie
                                                                  …see more

                                                                  Price per night from

                                                                  $85

                                                                  Price per night from

                                                                  $85

                                                                  (18) Very Good 

                                                                    22

                                                                    SV4205 2 bedroom, DIRECT OCEANFRONT, Wifi, BREATHTAKING VIEW.

                                                                    Island of Hawaii / Kailua-Kona

                                                                    Kailua-Kona apartment

                                                                    2 6 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Ask about children
                                                                    “Always a good experience” We have been using Knutson's services for many years and it has always been a pleasure doing business with them. Any calls for service have been promptly and cheerfully answered.
                                                                    …see more

                                                                    Price per night from

                                                                    $150

                                                                    Price per night from

                                                                    $150

                                                                    (16) Very Good 

                                                                      27

                                                                      Pahukoa Hale - Direct Ocean Front Hawaiian Style home in Kona Bay Estates

                                                                      Island of Hawaii / Kailua-Kona

                                                                      Kailua-Kona house

                                                                      3 8 min stay varies

                                                                      • 3 bedrooms
                                                                      • sleeps 8
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Ask about children
                                                                      “Some patina but well maintained and great location” The property is old (as we knew from the description) but in very good condition. We would suggest to add a water boiler since the antique stove is slow and inconvenient. But this is a minor issue, a
                                                                      …see more

                                                                      Price per night from

                                                                      $381

                                                                      Price per night from

                                                                      $381

                                                                      (11) Very Good 

                                                                        29

                                                                        Absolute Beachfront 2BD 2BA

                                                                        Island of Hawaii / Kailua-Kona

                                                                        Kailua-Kona apartment

                                                                        2 4 3 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 4
                                                                        • 3 nights min
                                                                        • Beach / lakeside relaxation
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        “Amazing!” What a wonderful place to stay on the Big Island. This condo is as nicely appointed as any place we have ever rented. The recently upgraded kitchen was particularly nice. The oceanfront location is truly wonderful. We watched turtles daily f
                                                                        …see more

                                                                        Price per night from

                                                                        $155

                                                                        Price per night from

                                                                        $155

                                                                        (14) Very Good 

                                                                          10

                                                                          Keauhou Gardens 3104, 1 BR.Garden NO BOOKING FEE

                                                                          Island of Hawaii / Kailua-Kona

                                                                          Kailua-Kona apartment

                                                                          1 2 min stay varies

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Car not necessary
                                                                          “Love the No Smoking, No Pets Rules” Condo is very relaxing and convenient. Since Keauhou Gardens is a No Smoking Resort, we did not have to put up with smoke drifting in from other condos or lanais and if we did Security would put a stop to it. Also
                                                                          …see more

                                                                          Price per night from

                                                                          $121

                                                                          Responds fast!
                                                                          avg. 3 hours 56 minutes

                                                                          Price per night from

                                                                          $121

                                                                            24

                                                                            Sea Village 2nd floor Direct Oceanfront unit with extensive upgrades

                                                                            Island of Hawaii / Kailua-Kona

                                                                            Kailua-Kona apartment

                                                                            2 6 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Ask about children
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $159

                                                                            Price per night from

                                                                            $159

                                                                            (23) Very Good 

                                                                              24

                                                                              Kona Bali Kai 317 Direct Oceanfront

                                                                              Island of Hawaii / Kailua-Kona

                                                                              Kailua-Kona apartment

                                                                              2 4 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Ask about children
                                                                              “#317 needs help” Over all thhe place was clean. But the tile floors need to be steam cleaned they are very DIRTY my feet on the bottom looked like I had been walking in mud from the first day on.
                                                                              …see more

                                                                              Price per night from

                                                                              $149

                                                                              Price per night from

                                                                              $149