Vacation Rentals with Pool in Wailea

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Filtering by: Swimming pool

1,515 vacation rentals

(6) Excellent 

    21

    Wailea Orchid Villa - Panoramic Views! 3 Bd/3 Ba

    Maui / Wailea

    Wailea villa

    3 8 min stay varies

    • 3 bedrooms
    • sleeps 8
    • min stay varies
    • Beach / lakeside relaxation
    • Nearest beach 0.1 mi
    • Swimming pool
    “Wonderful stay in the Penthouse Villa...” Service: 5 Stars - The owner was very prompt in replying to email with questions, concerns. Concierge and front desk staff were courteous and very helpful. The bellman/staff even brought all of our luggage
    …see more

    Price per night from

    $1,050

    Responds fast!
    avg. 1 hour 35 minutes

    Price per night from

    $1,050

    (12) Excellent 

      22

      Updated Spacious 3 Bdrm. Wailea Ocean View Condo

      Maui / Wailea

      Wailea apartment

      3 6 7 nights min

      • 3 bedrooms
      • sleeps 6
      • 7 nights min
      • Beach / lakeside relaxation
      • Swimming pool
      • Child Friendly
      “Great condo!” We absolutely loved the condo.  It was well appointed and spacious.  We hosted a gathering of about 20 people and the kitchen, dining, living spaces combined with the lanai comfortably held that many people. The location was perfect, ri
      …see more

      Price per night from

      $285

      Responds fast!
      avg. 3 hours 3 minutes

      Price per night from

      $285

      (1) Excellent 

        47

        Wailea Ekolu #406 2BD/2BA Panoramic Ocean View Near Beach, Full A/C, Sleeps 4

        Maui / Wailea

        Wailea apartment

        2 4 min stay varies

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

        Price per night from

        $255

        Responds fast!
        avg. 5 minutes

        Price per night from

        $255

        (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 35 minutes

          Price per night from

          $1,600

          (1) Very Good 

            38

            Palms at Wailea #1102 Probably the best ocean view at the Palms at Wailea!

            Maui / Wailea

            Wailea apartment

            2 6 min stay varies

            • 2 bedrooms
            • sleeps 6
            • min stay varies
            • Swimming pool
            • Child Friendly
            “Great place to stay for the price” We loved the location and views from our units. The pool was warm and quite nice despite having many restrictions. The units were clean and nice looking however many of the amenities promised (ie. beach equipment) we
            …see more

            Price per night from

            $295

            Responds fast!
            avg. 5 minutes

            Price per night from

            $295

              46

              Wailea Ekolu #205 2Bd/2Ba Ocean View, Ground Floor, Near Beach, Wifi Sleeps 6

              Maui / Wailea

              Wailea apartment

              2 6 min stay varies

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

              Price per night from

              $265

              Responds fast!
              avg. 5 minutes

              Price per night from

              $265

              (3) Excellent 

                47

                Grand Champions #151 is a1 Bd 2 Ba fronting the Wailea Golf Course. Sleeps 4.

                Maui / Wailea

                Wailea apartment

                1 4 min stay varies

                • 1 bedroom
                • sleeps 4
                • min stay varies
                • Swimming pool
                • Child Friendly
                • Air conditioning
                “Exceeded Expectations” I love this property. We had looked at alot of places and time was running out. When this property popped up, I never thought it looked liked the way it did in person. It looked better in person. We are definitely returning. Mah
                …see more

                Price per night from

                $159

                Responds fast!
                avg. 5 minutes

                Price per night from

                $159

                (15) Very Good 

                  49

                  Palms at Wailea Unit #2305 1Bd/2Ba Quiet, Very Private! Near Beach, Sleeps 2

                  Maui / Wailea

                  Wailea apartment

                  1 2 min stay varies

                  • 1 bedroom
                  • sleeps 2
                  • min stay varies
                  • Swimming pool
                  • Child Friendly
                  “Great for Couples” For those of us who hate living in hotels, or paying for services we don't use, this 1 bedroom/2 bathroom condo is perfect. It feels and looks even larger than the photos and is equipped with a full kitchen, that is very well stocke
                  …see more

                  Price per night from

                  $189

                  Responds fast!
                  avg. 5 minutes

                  Price per night from

                  $189

                  (31) Very Good 

                    34

                    Grand Champions #48 is a 2bd 2ba Ocean View condo that Sleeps 6 Great Rates!

                    Maui / Wailea

                    Wailea apartment

                    2 6 min stay varies

                    • 2 bedrooms
                    • sleeps 6
                    • min stay varies
                    • Swimming pool
                    • Child Friendly
                    • Air conditioning
                    “Best experience ever in USA. Loved every minute of our stay.” #51 @ #48 condos were by far even better than the reviews and pictures described. My family from Canada and myself were truly impressed by the attention to detail and how well the units wer
                    …see more

                    Price per night from

                    $220

                    Responds fast!
                    avg. 5 minutes

                    Price per night from

                    $220

                    (7) Very Good 

                      46

                      Wailea Ekolu 805 Deluxe 2Bd/2Ba, Ocean View Townhouse! Full A/C, Sleeps 4

                      Maui / Wailea

                      Wailea apartment

                      2 4 min stay varies

                      • 2 bedrooms
                      • sleeps 4
                      • min stay varies
                      • Swimming pool
                      • Child Friendly
                      • Air conditioning
                      “Ekolu Unit 805” Wailea Ekolu Unit 805 is a comfortable, clean, spacious, beautifully updated two bedroom/two bath condo. This first floor unit with a nice lanai has a partial view of the ocean and is located in a quiet area of the complex. I would not
                      …see more

                      Price per night from

                      $215

                      Responds fast!
                      avg. 5 minutes

                      Price per night from

                      $215

                        34

                        Wailea Ekolu #201 2Bd/2Ba Ocean View Condo Near Beach, A/C, Wifi, Sleeps 6

                        Maui / Wailea

                        Wailea apartment

                        2 6 min stay varies

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

                        Price per night from

                        $250

                        Responds fast!
                        avg. 5 minutes

                        Price per night from

                        $250

                          26

                          Palms at Wailea #205, 2Bd/2Ba, Luxurious, Spacious, Fantastic Location!

                          Maui / Wailea

                          Wailea apartment

                          2 6 min stay varies

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

                          Price per night from

                          $289

                          Responds fast!
                          avg. 5 minutes

                          Price per night from

                          $289

                          (19) Excellent 

                            32

                            Palms at Wailea #1105 Lovely Ocean View, 2Bd 2Bath, Great Rates! Sleeps 4

                            Maui / Wailea

                            Wailea apartment

                            2 4 min stay varies

                            • 2 bedrooms
                            • sleeps 4
                            • min stay varies
                            • Swimming pool
                            • Child Friendly
                            “Great Getaway!!” I loved unit 1105 at The Palms. It was totally updated and very clean. The beach chairs and boogie boards were nice to have. Loved the quiet nature of the Palms and the proximity to all of the beautiful beaches!!
                            …see more

                            Price per night from

                            $299

                            Responds fast!
                            avg. 5 minutes

                            Price per night from

                            $299

                            (14) Very Good 

                              30

                              Grand Champions #51 is a 2Bd 2Ba is a large condo that sleeps 6. Great Rates!

                              Maui / Wailea

                              Wailea apartment

                              2 6 min stay varies

                              • 2 bedrooms
                              • sleeps 6
                              • min stay varies
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning
                              “Exceeded expectations by a mile!” From the moment we arrived we were amazed at the way the condos we rented (we had #48 as well) were decorated, furnished and stocked with anything we could possibly have wanted for our holiday. Even items for the beac
                              …see more

                              Price per night from

                              $210

                              Responds fast!
                              avg. 5 minutes

                              Price per night from

                              $210

                              (2) Excellent 

                                23

                                Brand new 2 bedroom beach front at the Mana Kai Maui Resort! On Keawakapu beach!

                                Maui / Wailea

                                Wailea condo

                                2 6 3 nights min

                                • 2 bedrooms
                                • sleeps 6
                                • 3 nights min
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $630

                                Price per night from

                                $630

                                (1) Very Good 

                                  21

                                  Wailea Ekahi 46F- Spacious 2 bedroom 2 Bath Condo in Wailea!

                                  Maui / Wailea

                                  Wailea apartment

                                  2 6 min stay varies

                                  • 2 bedrooms
                                  • sleeps 6
                                  • min stay varies
                                  • Swimming pool
                                  • Ask about children
                                  “Great trip to Maui” My family and I enjoyed our time at Ekahi. Loved the view from the balconies, and chairs and other beach equipment was there for our use. The property management was very accomodating and when we had one thing missing from the cond
                                  …see more

                                  Price per night from

                                  $295

                                  Price per night from

                                  $295

                                  (4) Excellent 

                                    16

                                    Fantastic Beach Front 2 Bedroom Condo MAKENA SURF RESORT, #B-205

                                    Maui / Wailea

                                    Wailea apartment

                                    2 4 5 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 5 nights min
                                    • Swimming pool
                                    • Child Friendly
                                    • Car not necessary
                                    “Great Spot” Great beach snorkeling was so convenient lots of turtles. Quiet area but you can access whatever excitement you want in a short drive. The pool is right next to the condo so you can relax there as well. Very well kept grounds. Highly re
                                    …see more

                                    Price per night from

                                    $689

                                    Price per night from

                                    $689

                                    (20) Very Good 

                                      27

                                      Palms at Wailea #1902 Garden View 2Bd/2Ba, Fully Air Conditioned, Sleeps 6

                                      Maui / Wailea

                                      Wailea apartment

                                      2 6 min stay varies

                                      • 2 bedrooms
                                      • sleeps 6
                                      • min stay varies
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning
                                      “A breath of fresh air” I have stayed at many different rentals never knowing if the pictures show what the condo really looks like. This rental was exactly what was shown and more! We were impressed with the updated features and location. The balcony
                                      …see more

                                      Price per night from

                                      $245

                                      Responds fast!
                                      avg. 5 minutes

                                      Price per night from

                                      $245

                                      (17) Excellent 

                                        17

                                        Wailea Ekahi Ocean View 50A

                                        Maui / Wailea

                                        Wailea condo

                                        1 4 min stay varies

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

                                        Price per night from

                                        $252

                                        Responds fast!
                                        avg. 1 hour 48 minutes

                                        Price per night from

                                        $252

                                          31

                                          Oceanview Condo just Moments from the Beach

                                          Maui / Wailea

                                          Wailea condo

                                          2 6 7 nights min

                                          • 2 bedrooms
                                          • sleeps 6
                                          • 7 nights min
                                          • Swimming pool
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $373

                                          Price per night from

                                          $373

                                          (1) Excellent 

                                            33

                                            Spectacular 3rd Row at Ho'olei with Ocean Views

                                            Maui / Wailea

                                            Wailea villa

                                            3 8 6 nights min

                                            • 3 bedrooms
                                            • sleeps 8
                                            • 6 nights min
                                            • Swimming pool
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $853

                                            Responds fast!
                                            avg. 3 hours 12 minutes

                                            Price per night from

                                            $853

                                              36

                                              Just Renovated 3bd 3ba in South Kihei, Hawaii

                                              Maui / Wailea

                                              Wailea condo

                                              3 9 min stay varies

                                              • 3 bedrooms
                                              • sleeps 9
                                              • min stay varies
                                              • Swimming pool
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $567

                                              Price per night from

                                              $567

                                                26

                                                PSA303 Affordable Paradise! 2 Bd, 2 ba Across from Beach & Mountain /Ocean views

                                                Maui / Wailea

                                                Wailea condo

                                                2 4 1 night min

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

                                                Price per night from

                                                $172

                                                Responds fast!
                                                avg. 3 hours 33 minutes

                                                Price per night from

                                                $172

                                                (13) Excellent 

                                                  0

                                                  Wailea Sunset Bungalow

                                                  Maui / Wailea

                                                  Wailea house

                                                  2 4 5 nights min

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • 5 nights min
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Air conditioning
                                                  “Paradise at Wailea Sunset Bungalow” Our trip to Maui was fantastic, mostly due to the spectacular Wailea Sunset Bungalow. This home was stocked with absolutely everything a person or group could ever need for a week, even a month. We enjoyed the fam
                                                  …see more

                                                  Price per night from

                                                  $1,095

                                                  Price per night from

                                                  $1,095

                                                  (7) Excellent 

                                                    40

                                                    FLASH SALE 30% off April - limited space book NOW!

                                                    Maui / Wailea

                                                    Wailea condo

                                                    2 6 min stay varies

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

                                                    Price per night from

                                                    $224

                                                    Price per night from

                                                    $224

                                                    (8) Very Good 

                                                      30

                                                      Wailea Grand Champions #50 is a 2 Bd 2 Ba Upgraded Unit. It can sleep 6.

                                                      Maui / Wailea

                                                      Wailea apartment

                                                      2 6 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 6
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Air conditioning
                                                      “Loved it” Loved the area the condo was located. Very clean, and spacious. Kids loved the pool =)
                                                      …see more

                                                      Price per night from

                                                      $199

                                                      Responds fast!
                                                      avg. 5 minutes

                                                      Price per night from

                                                      $199

                                                      (8) Excellent 

                                                        31

                                                        The Perfect Location for a Relaxing Hawaiian Getaway - Grand Champions #103

                                                        Maui / Wailea

                                                        Wailea apartment

                                                        1 4 1 night min

                                                        • 1 bedroom
                                                        • sleeps 4
                                                        • 1 night min
                                                        • Beach / lakeside relaxation
                                                        • Swimming pool
                                                        • Child Friendly
                                                        “This is a beautiful condo, wonderfully maintained, in a great lo” We have stayed at many condos on Maui for years, and this is absolutely our favorite. We were lucky enough to be the first guests, and everything was even better than expected. The pho
                                                        …see more

                                                        Price per night from

                                                        $194

                                                        Responds fast!
                                                        avg. 1 hour 26 minutes

                                                        Price per night from

                                                        $194

                                                          10

                                                          IS214 2 Bed, 2 Bath Large Ocean View Condo

                                                          Maui / Wailea

                                                          Wailea condo

                                                          2 6 1 night min

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • 1 night min
                                                          • Nearest beach 0.01 mi
                                                          • Swimming pool
                                                          • Child Friendly

                                                          Price per night from

                                                          $201

                                                          Responds fast!
                                                          avg. 3 hours 33 minutes

                                                          Price per night from

                                                          $201

                                                            16

                                                            Gorgeous Remodeled Ocean Front Condo - Makena Surf Resort G-206

                                                            Maui / Wailea

                                                            Wailea apartment

                                                            2 4 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 4
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Car not necessary

                                                            Price per night from

                                                            $649

                                                            Price per night from

                                                            $649

                                                            (2) Very Good 

                                                              16

                                                              Beautiful Remodeled Ground Floor Unit- Wailea Ekahi 4C

                                                              Maui / Wailea

                                                              Wailea apartment

                                                              1 4 min stay varies

                                                              • 1 bedroom
                                                              • sleeps 4
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Car not necessary
                                                              “Pleasant” Though I was told that this was going to be on the beach. Not quite - but not a far walk either. Very good for couples but not so good for families. Some of the older folk looked at the kids and were not smiling :-( Very nice unit that
                                                              …see more

                                                              Price per night from

                                                              $235

                                                              Price per night from

                                                              $235

                                                              (1) Excellent 

                                                                24

                                                                Beautiful, Renovated, Hale Kamaole 159 now available! Walk to Kamaole III Beach!

                                                                Maui / Wailea

                                                                Wailea apartment

                                                                1 4 min stay varies

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

                                                                Price per night from

                                                                $201

                                                                Responds fast!
                                                                avg. 2 hours 34 minutes

                                                                Price per night from

                                                                $201

                                                                  23

                                                                  Maui Kamaole #A209 2BR/2BA - Spectacular Panoramic Ocean View in best location

                                                                  Maui / Wailea

                                                                  Wailea condo

                                                                  2 6 3 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 6
                                                                  • 3 nights min
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $373

                                                                  Price per night from

                                                                  $373

                                                                  (2) Excellent 

                                                                    50

                                                                    Castaway Cove C201 at Wailea Beach Villas

                                                                    Maui / Wailea

                                                                    Wailea house

                                                                    3 6 min stay varies

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

                                                                    Price per night from

                                                                    $1,145

                                                                    Price per night from

                                                                    $1,145

                                                                      16

                                                                      Remodeled Second Floor 2 BDRM Condo Wailea Elua Village # 202

                                                                      Maui / Wailea

                                                                      Wailea apartment

                                                                      2 5 5 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 5
                                                                      • 5 nights min
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Car not necessary

                                                                      Price per night from

                                                                      $440

                                                                      Price per night from

                                                                      $440

                                                                      (8) Excellent 

                                                                        10

                                                                        Great Ocean View Family Friendly GC#42

                                                                        Maui / Wailea

                                                                        Wailea apartment

                                                                        2 6 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Beach / lakeside relaxation
                                                                        • Nearest beach 0 mi
                                                                        • Swimming pool

                                                                        Price per night from

                                                                        $250

                                                                        Price per night from

                                                                        $250

                                                                        (5) Excellent 

                                                                          16

                                                                          Stunningly Remodeled Ocean View Unit -Wailea Ekahi #22D

                                                                          Maui / Wailea

                                                                          Wailea apartment

                                                                          1 4 5 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 4
                                                                          • 5 nights min
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Car not necessary

                                                                          Price per night from

                                                                          $299

                                                                          Price per night from

                                                                          $299

                                                                          (17) Very Good 

                                                                            39

                                                                            Palms at Wailea 702 Upstairs Garden View 1Bd/2Ba, Great Rates! Sleeps 4

                                                                            Maui / Wailea

                                                                            Wailea apartment

                                                                            1 4 min stay varies

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Air conditioning
                                                                            “Great Stay in #702” The unit was very spacious, very clean(the carpet had just been steam cleaned before we arrived) and is in great location in Wailea which is in the quieter part of Kihei. The lanai was large and perfect to spend the evening sipping
                                                                            …see more

                                                                            Price per night from

                                                                            $169

                                                                            Responds fast!
                                                                            avg. 5 minutes

                                                                            Price per night from

                                                                            $169

                                                                            (7) Excellent 

                                                                              8

                                                                              Remodeled Elegance & Luxury - Daily Housekeeping Elua Village # 2107

                                                                              Maui / Wailea

                                                                              Wailea apartment

                                                                              2 6 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Car not necessary
                                                                              “Maui Wailea Elua 2107” Very nice, comfortable 2 BR condo. In the upper tier of buildings in the development, so short walk down the hill to the beachwalk. Though nearer to the road, no noise in unit. Has a front lanai facing the ocean, landscaped b
                                                                              …see more

                                                                              Price per night from

                                                                              $399

                                                                              Price per night from

                                                                              $399