HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit

Make a self catering villa or holiday rental in Wailea, Maui, Hawaii your home away from home

Wailea offers a wonderful destination for a relaxing, low-key vacation in the sun on Hawaii’s second largest island. Maui offers spectacular scenery, volcanoes, beautiful beaches and great shopping. Wailea is a relatively new resort but it is rapidly increasing in popularity. Popular as an idyllic wedding or honeymoon destination, a holiday villa in Wailea makes the perfect base for exploring the island’s natural beauty and lush vegetation. The island is known for its sugar plantations, pineapple farms and its exotic flowers. Although there are plenty of bars and restaurants close to Wailea, nightlife is fairly quiet.

Things to do in Wailea, Maui

Golf

Wailea is well-known for its beautifully maintained golf courses, each hole offering spectacular scenery and unique challenges.

Beaches and Watersports

Maui has some of the best beaches in the world along with clear warm seas. Relax in the sun, or take a snorkel and flippers and explore the fantastic underwater world. The area also offers excellent diving, including the offshore volcanic crater close to Wailea. Shopping

There are plenty of opportunities for shopping in and around Wailea. Lahaina Cannery Mall is in a replica canning factory and has 50 speciality shops and restaurants in a fun location.

Places to visit near Wailea, Maui Hana Highway

One of the world’s most scenic drives can easily be enjoyed from your Wailea apartment in Maui. The winding 56-mile tour takes in old plantation towns, beaches, forests and the Haleakala Crater. Lahaina

A traditional Hawaiian evening is guaranteed at the Lahaina Luau with a delicious buffet of local dishes such as kalua pig and haupia (coconut pudding) alongside international dishes. The outdoor beachside setting is fantastic and the local entertainment is colourful and vibrant. Enjoy the local cultural activities including Hawaiian music, hula girls and even fire dancing.

Pineapple Plantation Tour

Almost one third of the world’s pineapples come from Maui. See how pineapples grow, ride a cart, pick your own juicy pineapple and watch a pineapple cutting demonstration at one of the many pineapple plantations close to your holiday rental home in Waimea.

Weather in Wailea, Maui

Wailea is well known for its year-round tropical warmth. Temperatures range between 79-84°F (26-29°C) from winter to summer although Maui does have a little rain each month from October to March which falls as occasional showers. The mountainous inland region has heavy rainfall throughout the year.

Travel to Wailea, Maui

The main Maui airport serving your holiday home in Wailea is Kahului airport which receives both inter-island and overseas flights. It is approximately 25 miles from Wailea.

Honolulu International airport is on the nearby island of Honolulu so a connecting flight to Maui would be needed.

  • Showing 1-50 of 300+
Additional service fee may apply.
    Exceptional! 5.0/5
    (47 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Separate Toilet
    • Sleeps 4
    Cottage #3617930
    47
    Viewed 279 times in the last 48 hours
      Wonderful! 4.8/5
      (25 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 4
      Condo #481883vb
      25
      Viewed 71 times in the last 48 hours
        Wonderful! 4.8/5
        (14 reviews)
        avg/night
        • 1 BR
        • 1 BA
        • Sleeps 2
        Condo #500715vb
        14
        Viewed 116 times in the last 48 hours
          Wonderful! 4.9/5
          (37 reviews)
          avg/night
          • 1 BR
          • 2 BA
          • Sleeps 4
          Condo #229577vb
          37
          Viewed 32 times in the last 48 hours
            Exceptional! 5.0/5
            (41 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 5
            House #502088vb
            41
            Viewed 138 times in the last 48 hours
              Wonderful! 4.8/5
              (11 reviews)
              avg/night
              • 1 BR
              • 2 BA
              • Sleeps 2
              Condo #4272970
              11
              Viewed 149 times in the last 48 hours
                Exceptional! 5.0/5
                (26 reviews)
                avg/night
                • 1 BR
                • 1 BA
                • Sleeps 2
                Condo #357286vb
                26
                Viewed 63 times in the last 48 hours
                  Exceptional! 5.0/5
                  (38 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 4
                  Cottage #92086vb
                  38
                  Viewed 104 times in the last 48 hours
                    avg/night
                    • 1 BR
                    • 2 BA
                    • Sleeps 4
                    Condo #927424vb
                    2
                    Viewed 69 times in the last 48 hours
                      Wonderful! 4.9/5
                      (33 reviews)
                      avg/night
                      • 2 BR
                      • 2 BA
                      • Sleeps 7
                      Condo #680284vb
                      33
                      Viewed 65 times in the last 48 hours
                        Exceptional! 5.0/5
                        (7 reviews)
                        avg/night
                        • 1 BR
                        • 2 BA
                        • Sleeps 2
                        Condo #408268vb
                        7
                        Viewed 27 times in the last 48 hours
                          Wonderful! 4.8/5
                          (13 reviews)
                          avg/night
                          • 1 BR
                          • 2 BA
                          • Sleeps 2
                          Condo #471127vb
                          13
                          Viewed 17 times in the last 48 hours
                            Exceptional! 5.0/5
                            (11 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            Condo #471550vb
                            11
                            Viewed 89 times in the last 48 hours
                              Wonderful! 4.8/5
                              (10 reviews)
                              avg/night
                              • 1 BR
                              • 2 BA
                              • Sleeps 4
                              Condo #329306vb
                              10
                              Viewed 30 times in the last 48 hours
                                Wonderful! 4.9/5
                                (57 reviews)
                                avg/night
                                • Studio
                                • 1 BA
                                • Sleeps 2
                                Condo #33820vb
                                57
                                Viewed 101 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (41 reviews)
                                  avg/night
                                  • 1 BR
                                  • 2 BA
                                  • Sleeps 4
                                  Apartment #424748vb
                                  41
                                  Viewed 86 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (112 reviews)
                                    avg/night
                                    • 1 BR
                                    • 2 BA
                                    • Sleeps 4
                                    Condo #144744vb
                                    112
                                    Viewed 111 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (6 reviews)
                                      avg/night
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 5
                                      Condo #882513vb
                                      6
                                      Viewed 44 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (19 reviews)
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Condo #694469vb
                                        19
                                        Viewed 79 times in the last 48 hours
                                          Excellent! 4.6/5
                                          (30 reviews)
                                          avg/night
                                          • Studio
                                          • 1 BA
                                          • Sleeps 2
                                          Condo #491236vb
                                          30
                                          Viewed 62 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (25 reviews)
                                            avg/night
                                            • Studio
                                            • 1 BA
                                            • Sleeps 3
                                            Studio #756478vb
                                            25
                                            Viewed 148 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (24 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Separate Toilet
                                              • Sleeps 8
                                              Condo #742008vb
                                              24
                                              Viewed 142 times in the last 48 hours
                                                Excellent! 4.5/5
                                                (24 reviews)
                                                avg/night
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 4
                                                Condo #436300vb
                                                24
                                                Viewed 64 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (12 reviews)
                                                  avg/night
                                                  • 1 BR
                                                  • 2 BA
                                                  • Sleeps 4
                                                  Condo #811955vb
                                                  12
                                                  Viewed 71 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (15 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 2 BA
                                                    • Sleeps 2
                                                    Condo #678888vb
                                                    15
                                                    Viewed 49 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (19 reviews)
                                                      avg/night
                                                      • 1 BR
                                                      • 2 BA
                                                      • Sleeps 3
                                                      Condo #579376vb
                                                      19
                                                      Viewed 77 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (18 reviews)
                                                        avg/night
                                                        • 1 BR
                                                        • 2 BA
                                                        • Sleeps 4
                                                        Condo #467442vb
                                                        18
                                                        Viewed 10 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (64 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 3
                                                          Condo #263305vb
                                                          64
                                                          Viewed 123 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (39 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 2 BA
                                                            • Sleeps 4
                                                            Condo #501619vb
                                                            39
                                                            Viewed 58 times in the last 48 hours
                                                              Excellent! 4.6/5
                                                              (5 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 4
                                                              Condo #895649vb
                                                              5
                                                              Viewed 89 times in the last 48 hours
                                                                Excellent! 4.7/5
                                                                (18 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 2 BA
                                                                • Sleeps 4
                                                                Condo #502643vb
                                                                18
                                                                Viewed 83 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (20 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 4
                                                                  Condo #472565vb
                                                                  20
                                                                  Viewed 28 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (40 reviews)
                                                                    avg/night
                                                                    • Studio
                                                                    • 1 BA
                                                                    • Sleeps 2
                                                                    Condo #28298vb
                                                                    40
                                                                    Viewed 78 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (11 reviews)
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 3
                                                                      Condo #4079566
                                                                      11
                                                                      Viewed 93 times in the last 48 hours
                                                                        Excellent! 4.7/5
                                                                        (20 reviews)
                                                                        avg/night
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Condo #51420vb
                                                                        20
                                                                        Viewed 135 times in the last 48 hours
                                                                          Exceptional! 5.0/5
                                                                          (40 reviews)
                                                                          avg/night
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 5
                                                                          Condo #293806vb
                                                                          40
                                                                          Viewed 34 times in the last 48 hours
                                                                            Wonderful! 4.8/5
                                                                            (28 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                            House #3590022
                                                                            28
                                                                            Viewed 121 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (17 reviews)
                                                                              avg/night
                                                                              • 1 BR
                                                                              • 2 BA
                                                                              • Sleeps 2
                                                                              Condo #695511vb
                                                                              17
                                                                              Viewed 41 times in the last 48 hours
                                                                                Excellent! 4.6/5
                                                                                (9 reviews)
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 2 BA
                                                                                • Sleeps 4
                                                                                Condo #156620
                                                                                9
                                                                                Viewed 59 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (22 reviews)
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 2
                                                                                  Condo #568230vb
                                                                                  22
                                                                                  Viewed 18 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (39 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    Condo #71926vb
                                                                                    39
                                                                                    Viewed 88 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (26 reviews)
                                                                                      avg/night
                                                                                      • 1 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 2
                                                                                      Condo #504483vb
                                                                                      26
                                                                                      Viewed 21 times in the last 48 hours
                                                                                        Wonderful! 4.8/5
                                                                                        (29 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 3
                                                                                        Cottage #25005vb
                                                                                        29
                                                                                        Viewed 62 times in the last 48 hours
                                                                                          Excellent! 4.7/5
                                                                                          (21 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 4
                                                                                          Condo #615427vb
                                                                                          21
                                                                                          Viewed 53 times in the last 48 hours
                                                                                            Excellent! 4.6/5
                                                                                            (14 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Condo #774987vb
                                                                                            14
                                                                                            Viewed 82 times in the last 48 hours
                                                                                              Exceptional! 5.0/5
                                                                                              (10 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 4
                                                                                              Condo #38686vb
                                                                                              10
                                                                                              Viewed 18 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (34 reviews)
                                                                                                avg/night
                                                                                                • 1 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 5
                                                                                                Condo #184640vb
                                                                                                34
                                                                                                Viewed 90 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (34 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 4
                                                                                                  Condo #68048vb
                                                                                                  34
                                                                                                  Viewed 66 times in the last 48 hours
                                                                                                    Exceptional! 5.0/5
                                                                                                    (38 reviews)
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 4
                                                                                                    Condo #339546vb
                                                                                                    38
                                                                                                    Viewed 30 times in the last 48 hours
                                                                                                      Exceptional! 5.0/5
                                                                                                      (24 reviews)
                                                                                                      avg/night
                                                                                                      • 1 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 4
                                                                                                      Condo #621837vb
                                                                                                      24
                                                                                                      Viewed 58 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Wailea Holiday Rentals & Homes (300+)