Where to stay around Wailea?

Our 2018 accommodation listings offer a large selection of 4,286 holiday lettings near Wailea. From 130 Houses to 102 Villas, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends. The best place to stay near Wailea for a long holiday or a weekend break is on HomeAway.

What are the most popular points of interest and landmarks to stay near when travelling to Wailea?

HomeAway offers a large selection of holiday accommodations near great places in Wailea. From HomeAway travellers, the most popular points of interest to stay near are:

  • Ahihi Kinau Natural Area Reserve: 4,315 holiday lettings
  • Ulua Beach Park: 4,545 holiday lettings
  • Shops at Wailea: 4,577 holiday lettings
  • Makena Golf Course: 4,358 holiday lettings
  • Keawakapu Beach: 4,655 holiday lettings

But there are many other points of interest around Wailea listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Wailea?

Yes, of course. HomeAway offers 130 Houses in Wailea. Our other popular types of Wailea holiday rentals include:

  • Villas: 102 self catering accommodations
  • Condos/Apartments: 38 self catering accommodations
  • Cottages: 23 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including Bungalows and more.

Can I rent beach rentals in Wailea?

Absolutely, HomeAway has 1,640 beach rentals in Wailea. You have also many other possibilities in Wailea area, including:

  • Waterfront rentals: 1,188 holiday rentals
  • Mountain rentals: 756 holiday rentals
  • Downtown rentals: 120 holiday rentals

Please use our search bar to access the selection of holiday lettings.

Can I find a holiday accommodation with pool in Wailea?

Yes, you can select your preferred holiday accommodation with pool among our 3,845 holiday homes with pool available in Wailea. Please use our search bar to access the selection of holiday rentals available.

    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


    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.

    Activities and attractions in and around Wailea

    Are you hoping to find things to do in the city? Travellers enjoy Wailea for its snorkelling, golfing and swimming. Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Wailea a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

    • Maui Ocean Center (11 mi / 17.7 km)
    • Wailea Gold Golf Course (0.9 mi / 1.5 km)
    • Wailea Emerald Golf Course (0.9 mi / 1.5 km)
    • Makena Golf Course (1 mi / 1.7 km)
    • Wailea Blue Golf Course (1.5 mi / 2.5 km)
    • Maui Nui Golf Club (6.6 mi / 10.7 km)

    Seasonal weather averages in Wailea

    Travellers speak highly of Wailea for its snorkelling. If you're planning a holiday around the weather, August, July, September and October are the hottest months to visit, when temperatures average 31°F.

    Exploring the beaches and other natural features in Wailea

    Wailea is famous for its beautiful ocean views, breathtaking sunsets and spectacular coral reefs. Whether you're an adventurous traveller or just want to take in the scenery, Wailea is a great place to spend some time outside. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

    • Haleakala National Park (17.9 mi / 28.7 km)
    • Wailea Beach (2.2 mi / 3.5 km)
    • Maui Nui Botanical Gardens (16.8 mi / 27 km)
    • Iao Valley State Park (17.4 mi / 27.9 km)
    • Maluaka Beach (1 mi / 1.6 km)
    • Po'olenalena Beach (1 mi / 1.7 km)