Discover a selection of 4,000 vacation rentals in Wailea 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 $239 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.
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Top rated rentals — Wailea
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Destination guide

Explore Wailea luxury rentals

If you like golf or the beach, Wailea is ideal for Maui luxury rentals. The resort community has stunning ocean views, spectacular beaches, and premier golf courses, such as the Wailea Emerald, Wailea Blue, and Wailea Gold courses. Wailea Beach is a favorite of travelers for snorkeling and surfing. For outdoor adventure, visit the Ahihi-Kinau Natural Area Reserve to explore a coastal lava field, or take the Hoapili Trail to Kanaio Beach. In town, you'll find urban experiences like delicious restaurants serving Hawaii Regional Cuisine, local shops and boutiques, and all types of entertainment.

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!

Activities

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.

Weather

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.

Beaches

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.

How to get there

How to get to and around Wailea

The nearest airport is in Kahului, HI (OGG), located 16.6 mi (26.8 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Kapalua, HI (JHM-West Maui), which is 26.6 mi (42.7 km) away.

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?

Our 2021 property listings offer a large selection of 3,905 vacation rentals around Wailea. From 309 house rentals to 3,565 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.