Hawaii Rentals with Pools

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Filtering by: Swimming pool

5,110 house rentals in Hawaii with pools

(6) Excellent 

    28

    One-of-a-Kind Maui Getaway!

    Maui / Wailea

    Wailea house

    4 10 min stay varies

    • 4 bedrooms
    • sleeps 10
    • min stay varies
    • Beach / lakeside relaxation
    • Nearest beach 3 mi
    • Swimming pool

    Price per night from

    $1,600

    Responds fast!
    avg. 1 hour 36 minutes

    Price per night from

    $1,600

    (38) Excellent 

      11

      Amazing Views Hale - 270 degree Stunning Views from 2 Story Poipu Beach House

      Kauai / Poipu

      Poipu house

      3 8 min stay varies

      • 3 bedrooms
      • sleeps 8
      • min stay varies
      • Swimming pool
      • Ask about children
      “Perfect Views and the pool was great...” Amazing Views Hale was a great vacation rental home. We had 5 adults and a 19 month old in our party. The views are "amazing" for sure and we loved sitting on the deck and overlooking the beaches of Poipu. T

      Price per night from

      $374

      Price per night from

      $374

      (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

        Price per night from

        $182

        Responds fast!
        avg. 59 minutes

        Price per night from

        $182

        (23) Excellent 

          28

          Waipouli Beach Resort's First-Class Luxury F203

          Kauai / Kapaa

          Kapaa apartment

          2 6 min stay varies

          • 2 bedrooms
          • sleeps 6
          • min stay varies
          • Beach / lakeside relaxation
          • Swimming pool
          • Child Friendly
          “Had a wonderful time” Condo was clean, quiet and beautiful. Gardens were lovely, pool gorgeous and an awesome beach. Close to resaurants and grocery stores. Ideal location to explore the whole island.

          Price per night from

          $210

          Price per night from

          $210

          (30) Excellent 

            19

            Maui Oceanfront Paradise See April- Oct Specials Act Fast

            Maui / Lahaina

            Lahaina apartment

            1 2 min stay varies

            • 1 bedroom
            • sleeps 2
            • min stay varies
            • Beach / lakeside relaxation
            • Swimming pool
            • Ask about children
            “Beautiful Ocean Front Studio” My wife and I just returned from our stay in this beautiful studio and we were very pleased. Thomas, the owner, was very responsive and great to work with! The location at the Royal Kahana is great with many places to w

            Price per night from

            $155

            Price per night from

            $155

            (14) Excellent 

              26

              Kahana Reef 212

              Maui / Lahaina

              Lahaina condo

              1 4 min stay varies

              • 1 bedroom
              • sleeps 4
              • min stay varies
              • Swimming pool
              • Child Friendly
              “Paradise perfect” The view was fabulous and the location of the condo was great! We enjoyed coming”home” and sitting on the deck and enjoying the views! The condo could use a little updating and the bedroom carpet replaced. The only drawbacks we fo

              Price per night from

              $100

              Price per night from

              $100

              (3) Excellent 

                28

                Pili Mai 1-G

                Kauai / Koloa

                Koloa house

                2 8 min stay varies

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

                Price per night from

                $249

                Responds fast!
                avg. 1 hour 29 minutes

                Price per night from

                $249

                (3) Excellent 

                  41

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

                  Island of Hawaii / Kailua-Kona

                  Kailua-Kona house

                  3 8 3 nights min

                  • 3 bedrooms
                  • sleeps 8
                  • 3 nights min
                  • Swimming pool
                  • Child Friendly

                  Price per night from

                  $349

                  Price per night from

                  $349

                  (11) Very Good 

                    21

                    Maui Beautiful Westside Beach Front Condo See May- Oct Discounted Reduced Rates

                    Maui / Lahaina

                    Lahaina apartment

                    1 4 5 nights min

                    • 1 bedroom
                    • sleeps 4
                    • 5 nights min
                    • Beach / lakeside relaxation
                    • Swimming pool
                    • Ask about children
                    “Paradise” The condo was very nice. It had everything we needed. We had a wonderful time there!! Thanks for being a part of making our vacation perfect!! Randy May

                    Price per night from

                    $165

                    Price per night from

                    $165

                    (14) Very Good 

                      28

                      Hale Kai # 220 – Your Home by the Sea in West Maui

                      Maui / Lahaina

                      Lahaina apartment

                      3 6 5 nights min

                      • 3 bedrooms
                      • sleeps 6
                      • 5 nights min
                      • Swimming pool
                      • Ask about children
                      “Great time/location” This is a great property for a large group. Everyone had a great time - a couple of things that would improve the place would be curtains or blinds as there is no way to block the outside sunshine and property lights at night maki

                      Price per night from

                      $400

                      Price per night from

                      $400

                      (20) Excellent 

                        37

                        SPECIAL: Maui Vista- only $104/night for avail nights September 5th-8th

                        Maui / Kihei

                        Kihei apartment

                        1 4 min stay varies

                        • 1 bedroom
                        • sleeps 4
                        • min stay varies
                        • Beach / lakeside relaxation
                        • Nearest beach 0.2 mi
                        • Swimming pool
                        “Close to great beaches all you need is your flip flops” This is our 3rd year staying in this condo. It is clean and has all the amenities including beach toys,coolers,and even suntan lotion. The property has a place to grill and a pool. It also has a

                        Price per night from

                        $119

                        Responds fast!
                        avg. 1 hour 21 minutes

                        Price per night from

                        $119

                        (23) Excellent 

                          17

                          Premier Townhome: Full A/C and X-Large Lanai, Ocean Close in the Heart of Poipu

                          Kauai / Poipu

                          Poipu apartment

                          2 4 min stay varies

                          • 2 bedrooms
                          • sleeps 4
                          • min stay varies
                          • Swimming pool
                          • Child Friendly
                          • Air conditioning
                          “Well equiped beautiful condo” Pc 20 has everything a visitor could wish for. The unit is beautifully maintained and appointed. The beaches are close by within a 3 to 10 minute walk. Poipu Crater is spectacularly landscaped filled with birds and the

                          Price per night from

                          $285

                          Responds fast!
                          avg. 3 hours 25 minutes

                          Price per night from

                          $285

                            23

                            Kihei Bay Vista #C-106 Best Location, Garden View, Sleeps 4, Great Rates!

                            Maui / Kihei

                            Kihei apartment

                            1 4 min stay varies

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

                            Price per night from

                            $109

                            Responds fast!
                            avg. 4 minutes

                            Price per night from

                            $109

                            (1) Excellent 

                              32

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

                              Island of Hawaii / Kailua-Kona

                              Kailua-Kona apartment

                              2 4 3 nights min

                              • 2 bedrooms
                              • sleeps 4
                              • 3 nights min
                              • 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.

                              Price per night from

                              $399

                              Price per night from

                              $399

                              (37) 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

                                Price per night from

                                $150

                                Price per night from

                                $150

                                (43) Excellent 

                                  17

                                  Maui Banyan-Ocean View Top Floor Condo!

                                  Maui / Kihei

                                  Kihei apartment

                                  2 6 min stay varies

                                  • 2 bedrooms
                                  • sleeps 6
                                  • min stay varies
                                  • Beach / lakeside relaxation
                                  • Nearest beach 0.16 mi
                                  • Swimming pool
                                  “One of the Best Condo's to stay in Maui” We loved our stay at this condo, the Owner made it very seemless to book and welcomed us with coffee and cookie souvenirs was terrific. All newly renovated and great patio to sit out at every evening, the whole

                                  Price per night from

                                  $177

                                  Price per night from

                                  $177

                                  (7) Excellent 

                                    35

                                    Pikake**Available for 2-30 night rental. Please call

                                    Oahu / Kahuku

                                    Kahuku apartment

                                    2 6 2 nights min

                                    • 2 bedrooms
                                    • sleeps 6
                                    • 2 nights min
                                    • Swimming pool
                                    • Ask about children
                                    “Thumbs Up” We rented 5 units for three days each and this unit was by far the nicest and all of the units were very nice. Mahalo nui loa.

                                    Price per night from

                                    $209

                                    Price per night from

                                    $209

                                    (31) Very Good 

                                      17

                                      Kihei Bay Surf #119 Completely Remodeled Show Stopper! Great Rates! Sleeps 3.

                                      Maui / Kihei

                                      Kihei studio

                                      Studio 3 min stay varies

                                      • Studio
                                      • sleeps 3
                                      • min stay varies
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning
                                      “Kihei Stay” I would consider coming back. Very affordable pricing. The unit has been upgraded (except for the TV). We did spot one cockroach, but those are native to the island. Location isn't uber busy, which I recommend for a mellow/relaxing vacatio

                                      Price per night from

                                      $99

                                      Responds fast!
                                      avg. 4 minutes

                                      Price per night from

                                      $99

                                      (23) Excellent 

                                      Certificate of Excellence

                                        17

                                        Beautiful New Oceanview Condo-Steps to the Beach

                                        Kauai / Kapaa

                                        Kapaa condo

                                        1 4 3 nights min

                                        • 1 bedroom
                                        • sleeps 4
                                        • 3 nights min
                                        • Beach / lakeside relaxation
                                        • Swimming pool
                                        • Child Friendly
                                        “Cozy & Perfect just like home!” We couldn't have been any happier with this condo!! It had everything we needed or wanted during our vacation to Kauai. The condo was very nice and clean and felt very cozy from the moment we walked in the door. Our fav

                                        Certificate of Excellence

                                        Price per night from

                                        $182

                                        Responds fast!
                                        avg. 3 hours 17 minutes

                                        Price per night from

                                        $182

                                        (1) Excellent 

                                          10

                                          Keauhou Gardens 11-303 1Br Ocean view

                                          Island of Hawaii / Kailua-Kona

                                          Kailua-Kona condo

                                          1 2 min stay varies

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

                                          Price per night from

                                          $130

                                          Responds fast!
                                          avg. 3 hours 40 minutes

                                          Price per night from

                                          $130

                                          (6) Very Good 

                                            25

                                            Waipouli Beach Resort D204

                                            Kauai / Kapaa

                                            Kapaa apartment

                                            2 6 min stay varies

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

                                            Price per night from

                                            $249

                                            Responds fast!
                                            avg. 1 hour 29 minutes

                                            Price per night from

                                            $249

                                            (131) Excellent 

                                              30

                                              Kamaole Sands 10-211 "OCEAN VIEW" Remodeled/Full A/C /Large Lanai/Great reviews!

                                              Maui / Kihei

                                              Kihei apartment

                                              1 4 min stay varies

                                              • 1 bedroom
                                              • sleeps 4
                                              • min stay varies
                                              • Beach / lakeside relaxation
                                              • Nearest beach 0 mi
                                              • Swimming pool
                                              “Perfect - just as described!” Kameole Sands is an ideal location - close to beaches, restaurants & easy drives to more. The unit is updated, spotlessly clean and has all one needs ( and more) to enjoy the paradise that is Maui. View from the lanai is

                                              Price per night from

                                              $175

                                              Responds fast!
                                              avg. 38 minutes

                                              Price per night from

                                              $175

                                              (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

                                                $170

                                                Price per night from

                                                $170

                                                (36) Excellent 

                                                  29

                                                  Private Gated Estate with Pool, Walk to Beach & Town, Quiet, Lush, Aloha Spirit!

                                                  Maui / Lahaina

                                                  Lahaina house

                                                  4 8 min stay varies

                                                  • 4 bedrooms
                                                  • sleeps 8
                                                  • min stay varies
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 0.1 mi
                                                  • Swimming pool
                                                  “3 generation getaway” The Lahaina Gatehouse was perfect for our group of grandparents, kids, their spouses and two grandsons ages 4 and 8 (8 people total). There's enough space for gatherings as well as getting away for privacy too. The saltwater po

                                                  Price per night from

                                                  $700

                                                  Price per night from

                                                  $700

                                                  (13) Excellent 

                                                    36

                                                    Waikiki Beach Tower! Direct Oceanfront!

                                                    Oahu / Honolulu

                                                    Honolulu hotel apartment

                                                    2 8 min stay varies

                                                    • 2 bedrooms
                                                    • sleeps 8
                                                    • min stay varies
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 0 mi
                                                    • Swimming pool

                                                    Price per night from

                                                    $399

                                                    Responds fast!
                                                    avg. 1 hour 1 minutes

                                                    Price per night from

                                                    $399

                                                    (10) Excellent 

                                                      58

                                                      # Beautiful Kihei Maui Condo - Menehune Shores 126

                                                      Maui / Kihei

                                                      Kihei condo

                                                      2 6 4 nights min

                                                      • 2 bedrooms
                                                      • sleeps 6
                                                      • 4 nights min
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 2 mi
                                                      • Swimming pool
                                                      “Felt right at home, great location” The condo was the perfect location for my family. I was glad the kitchen was fully stocked and had everything we needed. The beach chairs, toys and other gear provided were put to great use and it was nice we didn

                                                      Price per night from

                                                      $220

                                                      Price per night from

                                                      $220

                                                      (31) Very Good 

                                                        30

                                                        Wyndham Waikiki Beach Walk Resort

                                                        Oahu / Honolulu

                                                        Honolulu condo

                                                        2 8 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 8
                                                        • min stay varies
                                                        • Nearest beach 0.2 mi
                                                        • Swimming pool
                                                        • Child Friendly
                                                        “Hawaii five O” Great location great room for 8 people in a 2 bedroom apartment just the aircon was very noisy right in the middle of town easy walk to beach and restaurant cooking facilities were good

                                                        Price per night from

                                                        $286

                                                        Price per night from

                                                        $286

                                                        (12) Excellent 

                                                          25

                                                          KKSR3202 DIRECT OCEANFRONT, Spacious, 2nd Flr

                                                          Island of Hawaii / Kailua-Kona

                                                          Kailua-Kona apartment

                                                          2 6 3 nights min

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • 3 nights min
                                                          • Swimming pool
                                                          • Ask about children
                                                          “Great Location” We very much enjoyed our 6 nights in this condo, from morning breakfast on the balcony to watching the sunset. Location is superb - there are 2 beaches within walking distance and you can walk up a short hill to a great espresso and cr

                                                          Price per night from

                                                          $299

                                                          Price per night from

                                                          $299

                                                          (39) Excellent 

                                                            50

                                                            Fabulous Oceanfront/Ocean view condo! Free Wifi,A/C,Parking, Pool, Private Lanai

                                                            Maui / Kihei

                                                            Kihei apartment

                                                            2 6 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • min stay varies
                                                            • Beach / lakeside relaxation
                                                            • Swimming pool
                                                            • Child Friendly
                                                            “Wonderful accommodations” We stayed at Jean's condo for 2 weeks in Feb/March 2014. The condo was outstanding on the quiet end of Kihei Rd. This is a very nice condo with an island color scheme. The furnishings were comfortable both inside and on the l

                                                            Price per night from

                                                            $227

                                                            Responds fast!
                                                            avg. 35 minutes

                                                            Price per night from

                                                            $227

                                                            (81) Excellent 

                                                            Certificate of Excellence

                                                              26

                                                              Direct Oceanfront Studio Unit 307 -Valley Isle Resort

                                                              Maui / Lahaina

                                                              Lahaina apartment

                                                              1 2 min stay varies

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • min stay varies
                                                              • Beach / lakeside relaxation
                                                              • Swimming pool
                                                              • Ask about children
                                                              “Cute condo” Looking for a small quaint condo? This is it. Very nicely decorated. Loved it! Very relaxing. Beach right outside the patio. Hearing the waves at night was very soothing. Location great. Just a ride away to shopping n eateries. Beach right

                                                              Certificate of Excellence

                                                              Price per night from

                                                              $154

                                                              Responds fast!
                                                              avg. 2 hours 44 minutes

                                                              Price per night from

                                                              $154

                                                              (4) Excellent 

                                                                47

                                                                Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!

                                                                Oahu / Honolulu

                                                                Honolulu condo

                                                                2 8 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 8
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $399

                                                                Responds fast!
                                                                avg. 1 hour 1 minutes

                                                                Price per night from

                                                                $399

                                                                (6) Very Good 

                                                                  26

                                                                  Kihei Bay Surf #226 Studio Sleeps 3 Convenient, Near Beach, Great Rates!

                                                                  Maui / Kihei

                                                                  Kihei studio

                                                                  Studio 3 min stay varies

                                                                  • Studio
                                                                  • sleeps 3
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning
                                                                  “more than expected!” To our suprise the unit had boggie boards, louged chairs,umbrella for beach usaged. Kitchen fully equip however the ice maker is not hook up with the water supply,(w/c can be easily fix). The condo right across from the small beac

                                                                  Price per night from

                                                                  $89

                                                                  Responds fast!
                                                                  avg. 4 minutes

                                                                  Price per night from

                                                                  $89

                                                                  (3) Excellent 

                                                                    43

                                                                    Beautiful Beachfront Condo at Pono Kai Resort, Unit C-204, Kapaa, HI

                                                                    Kauai / Kapaa

                                                                    Kapaa apartment

                                                                    1 4 4 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 4
                                                                    • 4 nights min
                                                                    • Nearest beach 0.01 mi
                                                                    • Swimming pool
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $206

                                                                    Responds fast!
                                                                    avg. 55 minutes

                                                                    Price per night from

                                                                    $206

                                                                      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 3 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 2
                                                                      • 3 nights min
                                                                      • Swimming pool
                                                                      • Ask about children
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $218

                                                                      Price per night from

                                                                      $218

                                                                        23

                                                                        BEACHFRONT three bedroom oceanfront penthouse on the east side

                                                                        Kauai / Kapaa

                                                                        Kapaa apartment

                                                                        3 6 min stay varies

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

                                                                        Price per night from

                                                                        $498

                                                                        Responds fast!
                                                                        avg. 31 minutes

                                                                        Price per night from

                                                                        $498

                                                                          9

                                                                          Beautiful Studio with kitchen bugalow

                                                                          Molokai / Kaunakakai

                                                                          Kaunakakai house

                                                                          2 2 7 nights min

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

                                                                          Price per night from

                                                                          $130

                                                                          Responds fast!
                                                                          avg. 3 hours 33 minutes

                                                                          Price per night from

                                                                          $130

                                                                          (26) Excellent 

                                                                          Certificate of Excellence

                                                                            30

                                                                            Papakea Resort, Unit G-407

                                                                            Maui / Ka'anapali

                                                                            Ka'anapali apartment

                                                                            2 6 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 3 mi
                                                                            • Swimming pool
                                                                            “Beautiful condo and with breathtaking views...your own little bit of paradise” The condo is located in a most desirable and sought after area of the western coast of Maui. Being right on the beach, you will have breataking views and depending on the t

                                                                            Certificate of Excellence

                                                                            Price per night from

                                                                            $269

                                                                            Responds fast!
                                                                            avg. 3 hours 21 minutes

                                                                            Price per night from

                                                                            $269