Vacation Rentals with Hot Tub in Wailea

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800 vacation rentals

(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

    (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

      Price per night from

      $285

      Responds fast!
      avg. 3 hours 1 minutes

      Price per night from

      $285

      (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

        Price per night from

        $189

        Responds fast!
        avg. 5 minutes

        Price per night from

        $189

        (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

          Price per night from

          $159

          Responds fast!
          avg. 5 minutes

          Price per night from

          $159

          (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

            Price per night from

            $1,050

            Responds fast!
            avg. 1 hour 28 minutes

            Price per night from

            $1,050

            (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!!

              Price per night from

              $299

              Responds fast!
              avg. 5 minutes

              Price per night from

              $299

              (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

                Price per night from

                $345

                Responds fast!
                avg. 5 minutes

                Price per night from

                $345

                (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

                  Price per night from

                  $210

                  Responds fast!
                  avg. 5 minutes

                  Price per night from

                  $210

                    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

                      33

                      New Listing! Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

                      Maui / Wailea

                      Wailea villa

                      3 8 6 nights min

                      • 3 bedrooms
                      • sleeps 8
                      • 6 nights min
                      • Child Friendly

                      Price per night from

                      $796

                      Responds fast!
                      avg. 3 hours 12 minutes

                      Price per night from

                      $796

                      (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

                        Price per night from

                        $220

                        Responds fast!
                        avg. 5 minutes

                        Price per night from

                        $220

                        (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

                          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

                            Price per night from

                            $245

                            Responds fast!
                            avg. 5 minutes

                            Price per night from

                            $245

                            (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

                              Price per night from

                              $194

                              Responds fast!
                              avg. 1 hour 26 minutes

                              Price per night from

                              $194

                              (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

                                (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

                                  Price per night from

                                  $925

                                  Price per night from

                                  $925

                                  (7) Excellent 

                                    40

                                    FLASH SALE 30% off May - 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

                                    $223

                                    Price per night from

                                    $223

                                    (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

                                      Price per night from

                                      $169

                                      Responds fast!
                                      avg. 5 minutes

                                      Price per night from

                                      $169

                                        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

                                          16

                                          WAILEA ELUA, #0702

                                          Maui / Wailea

                                          Wailea apartment

                                          2 6 5 nights min

                                          • 2 bedrooms
                                          • sleeps 6
                                          • 5 nights min
                                          • Ask about children
                                          • Ask about pets

                                          Price per night from

                                          $409

                                          Price per night from

                                          $409

                                          (1) Excellent 

                                            41

                                            STOP! LOOK NO FURTHER! Palms at Wailea #1503 2Bd Ocean View Best Location!

                                            Maui / Wailea

                                            Wailea apartment

                                            2 4 min stay varies

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

                                            Price per night from

                                            $360

                                            Responds fast!
                                            avg. 5 minutes

                                            Price per night from

                                            $360

                                            (19) Excellent 

                                              25

                                              PREMIUM UPSCALE GEM #1 UNIT-THE PALMS at WAILEA-GALLERY SETTING CONTEMPORARY GEM

                                              Maui / Wailea

                                              Wailea apartment

                                              1 4 4 nights min

                                              • 1 bedroom
                                              • sleeps 4
                                              • 4 nights min
                                              • Swimming pool
                                              • Ask about children
                                              • Car not necessary
                                              “Happy with our stay” We enjoyed our stay. The location was very close to the beach and a pool, and there were chairs and gear we could use which was great. The room itself was quite nice and comfortable, including an excellent entertainment system and

                                              Price per night from

                                              $286

                                              Responds fast!
                                              avg. 3 hours 24 minutes

                                              Price per night from

                                              $286

                                                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

                                                  16

                                                  Beautiful Views and Location - Wailea Grand Champions #163

                                                  Maui / Wailea

                                                  Wailea apartment

                                                  2 5 min stay varies

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

                                                  Price per night from

                                                  $189

                                                  Price per night from

                                                  $189

                                                    45

                                                    HO'OLEI #24-3-BEAUTIFULLY APPOINTED VILLA-SLEEPS 10

                                                    Maui / Wailea

                                                    Wailea condo

                                                    3 10 min stay varies

                                                    • 3 bedrooms
                                                    • sleeps 10
                                                    • min stay varies
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $700

                                                    Price per night from

                                                    $700

                                                    (7) Very Good 

                                                      16

                                                      Fantastic Location - Beautiful Oceanfront Condo -Makena Surf Resort # E-205

                                                      Maui / Wailea

                                                      Wailea apartment

                                                      2 6 5 nights min

                                                      • 2 bedrooms
                                                      • sleeps 6
                                                      • 5 nights min
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Car not necessary
                                                      “Wonderful location, great service” The condo was clean, wonderfully furnished, and offered adequate space for our family of six. We enjoyed the complex for its beautiful landscaping, grills, and easy access to the beach. We went in early December, a

                                                      Price per night from

                                                      $612

                                                      Price per night from

                                                      $612

                                                        40

                                                        HO'OLEI #93-2-BEAUTIFULLY APPOINTED VILLA-SLEEPS 8

                                                        Maui / Wailea

                                                        Wailea condo

                                                        3 8 min stay varies

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

                                                        Price per night from

                                                        $710

                                                        Price per night from

                                                        $710

                                                          15

                                                          Upgraded Condo- Beachfront- Easy Beach Access- MAKENA SURF RESORT, #B-204

                                                          Maui / Wailea

                                                          Wailea apartment

                                                          2 6 5 nights min

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • 5 nights min
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Car not necessary

                                                          Price per night from

                                                          $689

                                                          Price per night from

                                                          $689

                                                            15

                                                            Beautiful Views Await You Here - WAILEA ELUA, #1002

                                                            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

                                                            $749

                                                            Price per night from

                                                            $749

                                                            (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

                                                              Price per night from

                                                              $379

                                                              Price per night from

                                                              $379

                                                              (14) Excellent 

                                                                24

                                                                Maui Rendezvous Wailea Ekahi 33A Luxury Resort, Beach - 3 min. walk, Remodeled

                                                                Maui / Wailea

                                                                Wailea apartment

                                                                1 5 4 nights min

                                                                • 1 bedroom
                                                                • sleeps 5
                                                                • 4 nights min
                                                                • Beach / lakeside relaxation
                                                                • Swimming pool
                                                                • Child Friendly
                                                                “Relaxing and Beautiful Getaway” My husband and I stayed at 33a in Ekahi for a week long vacation. The condo and surroundings exceeded all of our expectations. It is very tastefully decorated, extremely clean with all the amenities needed for a relaxin

                                                                Price per night from

                                                                $315

                                                                Price per night from

                                                                $315

                                                                  16

                                                                  Beautiful Oceanfront Ground Floor Unit MAKENA SURF RESORT, #G-101

                                                                  Maui / Wailea

                                                                  Wailea apartment

                                                                  2 6 min stay varies

                                                                  • 2 bedrooms
                                                                  • sleeps 6
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Car not necessary

                                                                  Price per night from

                                                                  $599

                                                                  Price per night from

                                                                  $599

                                                                  (3) Excellent 

                                                                    14

                                                                    SPECIAL SUMMER RATE FOR AN "ALOHA" OCEAN VIEW AT MAUI KAMAOLE G-212

                                                                    Maui / Wailea

                                                                    Wailea condo

                                                                    2 4 4 nights min

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

                                                                    Price per night from

                                                                    $298

                                                                    Price per night from

                                                                    $298

                                                                      16

                                                                      Beautifully Renovated 2 BDRM WAILEA ELUA, #2201

                                                                      Maui / Wailea

                                                                      Wailea apartment

                                                                      2 6 min stay varies

                                                                      • 2 bedrooms
                                                                      • sleeps 6
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Car not necessary

                                                                      Price per night from

                                                                      $399

                                                                      Price per night from

                                                                      $399

                                                                      (13) Very Good 

                                                                        16

                                                                        Stunning Golf & Ocean Views - Wailea Grand Champions #180

                                                                        Maui / Wailea

                                                                        Wailea apartment

                                                                        3 6 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        • Car not necessary
                                                                        “A little piece of paradise!” Our family loved our stay! The kids enjoyed the pools and we loved our ocean view. We even loved the birds who woke us up each morning. We did the short drive down to Big Beach and ahihi Cove, we also walked down to Uluu

                                                                        Price per night from

                                                                        $229

                                                                        Price per night from

                                                                        $229

                                                                        (15) Very Good 

                                                                          43

                                                                          Palms at Wailea #1501 Ocean View Inner Court Ground Floor 1Bd 1Ba Sleeps 4

                                                                          Maui / Wailea

                                                                          Wailea apartment

                                                                          1 4 min stay varies

                                                                          • 1 bedroom
                                                                          • sleeps 4
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          “Enjoyable Stay!” Our overall experience was good. The property was quite comfortable. We loved the beautiful landscaping BUT the view of the ocean could be enhanced with a bit of selective trimming of the shrubs surrounding the patio area. The propert

                                                                          Price per night from

                                                                          $235

                                                                          Responds fast!
                                                                          avg. 5 minutes

                                                                          Price per night from

                                                                          $235

                                                                            24

                                                                            Romantic, Elegant, Sensual Retreat

                                                                            Maui / Wailea

                                                                            Wailea condo

                                                                            1 2 min stay varies

                                                                            • 1 bedroom
                                                                            • sleeps 2
                                                                            • min stay varies
                                                                            • Beach / lakeside relaxation

                                                                            Price per night from

                                                                            $281

                                                                            Price per night from

                                                                            $281

                                                                            (6) Very Good 

                                                                              30

                                                                              Palms at Wailea #604 2Bd/2Ba, Fully Air Conditioned, Great Rates! Sleeps 6

                                                                              Maui / Wailea

                                                                              Wailea apartment

                                                                              2 6 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Air conditioning
                                                                              “As seen on the website” Unit 604 definitely met and surpassed our expectations. The booking process, checking in, and checking out were a breeze. We were a large group, with 3 units rented (from different companies) and ours was definitely the best de

                                                                              Price per night from

                                                                              $189

                                                                              Responds fast!
                                                                              avg. 5 minutes

                                                                              Price per night from

                                                                              $189