Where to stay around Wailea, HI?

Our 2018 property listings offer a large selection of 4,518 vacation rentals near Wailea. From 4,086 Condos/Apartments to 122 Houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Wailea for a holiday or a weekend are on VRBO.

What are the popular point of interests near where I can stay when traveling to Wailea?

VRBO offers a large selection of vacation rentals near lovely places in Wailea. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Ulua Beach: 4,816 vacation rentals
  • Shops at Wailea: 4,804 vacation rentals
  • Keawakapu Beach: 4,918 vacation rentals
  • Ulua Beach Park: 4,815 vacation rentals
  • Makena Golf Course: 4,594 vacation rentals

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

Can I rent Condos/Apartments in Wailea?

Yes, of course. VRBO has 4,086 Condos/Apartments in Wailea. Our other popular types of vacation rentals in Wailea include:

  • Houses: 122 rentals available
  • Villas: 105 rentals available
  • Studios: 89 rentals available

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

Can I find a vacation rental with pool in Wailea?

Yes, you can select your prefered vacation rental with pool among our 4,033 vacation rentals with pool available in Wailea. Please use our search bar to access the selection of vacation rentals available.

    Wailea-Fit for a Goddess

    Legend has is it that Wailea, ‘The Waters of Lea’, got its name when a goddess took the shape of a beautiful bird and flew over its magnificent shoreline. In World War 2 US Marines prepared for battle at Wailea, but now it's among Maui’s most tranquil beach resorts. Visitors can enjoy more than 1,500 acres of lush tropical gardens and parkland, 2 miles of sun-kissed beach, and captivating views of the Pacific Ocean. Make the most of Wailea’s serene setting and book a Wailea vacation rental to be near the picturesque beaches, ocean views and many other attractions.

    Saddle up and mosey on down in Wailea

    The sun shines year round in Wailea, so there's never a bad time to head down to Wailea Beach. Voted 'America's best beach' in 1999, it's the area's most popular spot to catch some rays, ride some waves or just frolic in the water. If it's some adventure you're after, then saddle up at Ulupalakua Ranch. Guided horseback tours wind through Maui's lush interior, and along its majestic shore, and cater to riders of all abilities. If golf's more your thing, then you'll not be disappointed either, as Wailea has 3 18-hole courses.

    Don't forget to bring your appetite to Wailea

    Among Wailea's more elusive residents are Spinner Dolphins. These beautiful creatures are best glimpsed at Le Perouse Bay, a lava-shaped bay and one end of Maui's historic King's Trail. As the day draws to a close, head to scenic Keawakapu Beach and stake out a good spot to catch Maui's world-famous sunset. And if you want the complete Hawaiian experience, then check out the Grand Luau at Honua'ula. There you'll be treated to spectacular fire performers, Hula dancers, and a mouth-watering all-you-can-eat buffet, so you might want to let your belt out a notch or two!

    Don't forget to bring some sunscreen

    Whatever else you do, pack sunscreen. Wailea's tropical climate means it's warm and sunny all year round. While July and August are the hottest months with temperatures soaring into the high 80s, all the other months of the year experience average highs in excess of 80 F. Rain showers are common, particularly in December and January, although they tend to short and light, and while it can be humid in Wailea, it's not as stifling as it can be in other tropical climes. With such pleasant year-round weather, there's never a bad time to book a Wailea vacation rental.

    Go with the lava flow in Makena State Park

    Head to Makena State Park, just south of Wailea, where the eerie volcanic terrain has been largely untouched by human hands, and features undisturbed beaches and lava-formed outcrops, as well as Puʻu Olai, a 360-foot tall dormant volcanic cinder cone. To see Maui in all its untamed glory, head to Haleakalā National Park. Just over an hour's drive from your Wailea vacation rental, its stark volcanic mountains contrast with its subtropical rainforest, and is home to many endangered species of bird.