Vacation Rentals & Condos in Wailea

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1,870 condos

(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

      $284

      Responds fast!
      avg. 3 hours 1 minutes

      Price per night from

      $284

      (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

            (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

              (35) Excellent 

                30

                OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA

                Maui / Wailea

                Wailea cottage

                1 3 3 nights min

                • 1 bedroom
                • sleeps 3
                • 3 nights min
                • Beach / lakeside relaxation
                • Nearest beach 2 mi
                • Air conditioning
                “Wonderful view and property” This was the perfect place for our annual stay on Maui. Dennis is the best host and takes care of any request you may have. The cottage is newly updated with all the conveniences and space needed. It is a very quiet are

                Price per night from

                $248

                Responds fast!
                avg. 2 hours 15 minutes

                Price per night from

                $248

                (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

                  (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

                      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

                      (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

                        Price per night from

                        $215

                        Responds fast!
                        avg. 5 minutes

                        Price per night from

                        $215

                        (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

                          $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

                            (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

                              (18) 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 45 minutes

                                Price per night from

                                $252

                                  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

                                  (1) Excellent 

                                    15

                                    Maui Wailea Townhouse, 2BR, 2.5 Ba, air conditioned, sleeps 8, ocean view

                                    Maui / Wailea

                                    Wailea apartment

                                    2 8 4 nights min

                                    • 2 bedrooms
                                    • sleeps 8
                                    • 4 nights min
                                    • Nearest beach 1 mi
                                    • Child Friendly

                                    Price per night from

                                    $217

                                    Responds fast!
                                    avg. 3 hours 32 minutes

                                    Price per night from

                                    $217

                                      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

                                      $791

                                      Responds fast!
                                      avg. 3 hours 12 minutes

                                      Price per night from

                                      $791

                                      (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

                                          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

                                          $371

                                          Price per night from

                                          $371

                                          (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

                                            (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

                                              Price per night from

                                              $295

                                              Price per night from

                                              $295

                                              (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

                                                $851

                                                Responds fast!
                                                avg. 3 hours 12 minutes

                                                Price per night from

                                                $851

                                                (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

                                                    $193

                                                    Responds fast!
                                                    avg. 1 hour 26 minutes

                                                    Price per night from

                                                    $193

                                                    (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

                                                          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

                                                            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

                                                            $372

                                                            Price per night from

                                                            $372

                                                            (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

                                                              (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

                                                                $199

                                                                Responds fast!
                                                                avg. 2 hours 34 minutes

                                                                Price per night from

                                                                $199

                                                                (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

                                                                  (5) Excellent 

                                                                    16

                                                                    Stunningly Remodeled Ocean View Unit -Wailea Ekahi #22D

                                                                    Maui / Wailea

                                                                    Wailea apartment

                                                                    1 4 min stay varies

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

                                                                    Price per night from

                                                                    $279

                                                                    Price per night from

                                                                    $279

                                                                    (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 =)

                                                                      Price per night from

                                                                      $199

                                                                      Responds fast!
                                                                      avg. 5 minutes

                                                                      Price per night from

                                                                      $199

                                                                        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

                                                                        (1) Very Good 

                                                                          45

                                                                          New Listing Budget Vacation! Kihei Akahi C-616

                                                                          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

                                                                          $168

                                                                          Responds fast!
                                                                          avg. 3 hours 34 minutes

                                                                          Price per night from

                                                                          $168

                                                                            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

                                                                              About Wailea

                                                                              Famous for its five half-moon shaped beaches and world-class golf courses, Wailea is five times the size of Honolulu’s Waikiki with unmatched Pacific Ocean views. For a luxurious Hawaiian vacation in a very sought-after location, visit FlipKey where you will find a Wailea vacation rental to suit all your needs.

                                                                              About Wailea

                                                                              Wailea is located on the south-western part of Hawaiian Island of Maui, just 14 miles from Kahului Airport.

                                                                              Meticulously laid out over 1,500 acres of lush tropical vegetation, the beach at Wailea is one of the most visited on Maui. The popularity of the beach is partly due to the area’s luxurious oceanfront resorts and spas, as well as its legendary year-round average temperature of 82 degrees!

                                                                              Even the shopping at Wailea has an upmarket feel with Gucci, Louis Vuitton, Prada and Tiffany & Co all represented next to surfing boutiques such as Quicksilver, Rip Curl and the Honolulu Surfing Company.

                                                                              When it comes to fine dining, you will be spoilt for choice with American, international and Hawaiian specialties all available.

                                                                              Top Wailea events include the February Whale Week and the Maui Film Festival. See if you can catch one during your stay!

                                                                              What to do

                                                                              Avid golfers flock to Wailea just to play the Gold Course (one of the top golfing destinations in the country!). Robert Trent Jones II designed championship course that takes advantage of the natural surroundings, while incorporating stunning ocean views from every tee. A true thinking man’s course, and considered one of the best designed courses in the world.

                                                                              Hawaii is, of course, all about surfing and Maui has its fair share of top spots where the pros come to catch big winter waves. But on the south of the island, the waves are around three feet in height, making them perfect for beginners.

                                                                              Go hiking in the Haleakala National Park and climb to the top of the world’s largest dormant volcano, Haleakala, where you will be rewarded with fantastic views of the island.

                                                                              Top Wailea travel tips

                                                                              With almost perfect weather all year round, there is no bad time to visit Wailea.

                                                                              For beach attire, avoid the fancy stores and ask the locals where they go shopping, instead. Consider buying a snorkel, mask, and fins as it can actually work out cheaper than renting.

                                                                              Hawaii is a no-brainer for a tropical beach vacation, but with so many great amenities, Wailea truly is a world-class destination. To find your slice of paradise, FlipKey has dozens of Wailea vacation rentals to suit all budgets.