Discover a selection of 4,000 vacation rentals in Wailea, HI that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $140 per night, and houses and condos are popular options for a stay in Wailea. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Wailea
Destination guide

Paradise at Wailea vacation home rentals

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.

Things to do

Attractions near Wailea vacation rentals

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!


Things to do near Wailea vacation homes

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.


Local weather for your stay in Wailea vacation homes

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.

Natural features

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.


Best beaches near Wailea vacation homes

Wailea has gorgeous beaches suited to different activities and adventures. Vacation homes are available near places like Makena Alanui, a tranquil beach with clear waters for snorkeling and a native population of sea turtles, and Polo Beach Park, a white-sand beach with a natural backdrop and trails. You'll also like Molokini, a crescent islet with vibrant marine life to explore with snorkeling.

Good for couples

Couple's retreat near Wailea vacation rentals

The idyllic surrounds and fun-filled activities of Wailea make it ideal for a couple’s getaway. Vacation homes are available near places like Maui Tropical Plantation, a working farm with tours of sugarcane and pineapple fields, and Ali’I Kula Lavender, a sprawling lavender farm with tours and a gift shop with products. You'll also enjoy Ahihi-Kinau Natural Area Reserve, a protected coastal lava field with diverse wildlife, sandy beaches, and turquoise waters popular for diving and snorkeling.

How many vacation rentals are available around Wailea, HI?

Our 2022 property listings offer a large selection of 4,245 vacation rentals around Wailea. From 343 house rentals to 3,812 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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:

  • Wailea Blue Golf Course: 4,264 vacation rentals
  • Wailea Gold Golf Course: 4,249 vacation rentals
  • Ulua Beach Park: 4,346 vacation rentals
  • Wailea Emerald Golf Course: 4,243 vacation rentals
  • Wailea Shopping Village Shopping Center: 4,387 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 Houses in Wailea?

Yes, of course. Vrbo has 343 Houses in Wailea. Our other popular types of vacation rentals in Wailea include:

  • Condos/Apartments: 3,812 rentals available
  • Villas: 106 rentals available
  • Resorts: 12 rentals available

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

Can I find a vacation rental with pool in Wailea?

Yes, you can select your preferred vacation rental with pool among our 3,895 vacation rentals with pool available in Wailea. Please use our search bar to access the selection of vacation rentals available.