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.

What are the top vacation rentals in or near Wailea?

Whether you're after an intimate escape for you and your special someone or somewhere roomy to fit friends and family, you'll find some top vacation rentals in and around Wailea. Here are a couple to start you off:

  • Around 6 miles from the center of Wailea, you'll love staying at Amazing Ocean View, Top Floor, Across St From Beach. It has 1 bedroom and a range of amenities including nearby whale-watching activities and children's toys.
  • Another great choice is Upcountry Kula - Private House On The Slopes Of Haleakala, which is around 11 miles from Wailea. With 2 bedrooms, a TV and an electric kettle, it has everything you need to keep you comfortable and content.

For even more great options, use the search bar at the top of the page to find the perfect Wailea vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Wailea?

Clock out on Friday afternoon and then forget all about work. If you're in the mood for some relaxation and fun, these rentals in and around Wailea are the perfect weekend getaway:

  • Whaler 502 - Fabulous Direct Oceanfront 2bedroom 2ba W is a favorite option around 25 miles northwest of central Wailea. You'll never have to go far to find something cool to do around this retreat. Get out and visit Makena Golf Course and Whalers Village Museum. Activities like a stovetop and air conditioning will add a nice finishing touch to your weekend trip.
  • Kihei Oasis Permitted Private Home 1 is another great setting for a weekend getaway. Around 8 miles north of Wailea, use it as a base to enjoy some an ice maker or a living room. Makena Landing Park and Kamaole Beach Park 2 should also be on your itinerary while you're here.

What are the best romantic weekend getaways in or near Wailea?

Forget about roses and chocolates. Sometimes all you need is to get away for a weekend, just you and your beloved. At Vrbo, we've got romantic getaways in and around Wailea that would make Cupid green with envy. Here are some we think you'll fall hard for:

  • Put on some love songs and chill together at Amazing Ocean View, Top Floor, Across St From Beach. Around 6 miles from Wailea, this property has all you need for a romantic weekend getaway, including a balcony and a heated pool.
  • Upcountry Kula - Private House On The Slopes Of Haleakala is another retreat that's bound to impress. It's about 11 miles from Wailea and has beach sun loungers and spa and beauty services.

What's the best place to stay if you're looking to rent a house for a weekend in or near Wailea?

If spending a few leisurely days by the sea is your idea of the ultimate weekend escape, look no further than Napili. It's around 30 miles northwest of Wailea and home to Napili Bay Beach.

What are the best large group vacation rentals in or near Wailea?

Big groups mean gigantic fun. They also mean finding a place that'll easily fit your entire squad. Check out our large group vacation rentals in or around Wailea and get everybody together under the same roof:

  • You'll have loads of space to enjoy yourselves at Island View - 2 Bedroom - Marriott's Maui Ocean Club: Lahaina - Marriott's Maui Ocean Club. Around 25 miles northwest of Wailea, this generously sized retreat has 2 bedrooms accommodating up to 15 guests. Amenities include optional golf privileges and a microwave oven.
  • Invite as many as 15 of your closest friends to Island View - 2 Bedroom - Marriott's Maui Ocean Club: Lahaina - Marriott's Maui Ocean Club and fill its spaces with laughter and love. This popular option has 2 bedrooms and is around 25 miles to the northwest of central Wailea. It's packed with features to keep a large group happy and comfortable, such as air conditioning and a balcony.

What are the best houses for rent with a pool in or near Wailea?

Having access to a pool is almost a must when you're on vacation, especially if you're bringing the kids. Splash the days away at one of these houses with a pool in or near Wailea:

  • At the top of our list of cool pool retreats is Upcountry Kula - Private House On The Slopes Of Haleakala. Traveling groups will feel at home here, with amenities like a DVD player and cookware, dishware and utensils also at hand.
  • Another top-rated option is Family - Friendly Housewalk To Beach. There's lots to love about this property besides its pool, such as a fenced yard and an oven.

What are the best large family vacation rentals in or near Wailea?

It's always more fun to share those memorable moments with the ones closest to your heart. Whether you're planning a family trip or celebrating a special occasion with close friends, we'll have a large vacation rental that suits you. Here are two of our best in and around Wailea:

  • Around 6 miles to the north of Wailea, Family - Friendly Housewalk To Beach has 4 bedrooms and sleeps up to 8 guests. It comes with a range of amenities, including books and a boat.
  • Another popular option is Ocean View, Close To Beach And Pool. This vacation rental is 2 miles north of Wailea and features a dishwasher, a smart TV and more. With 3 bedrooms accommodating up to 10 people, don't worry about leaving anyone off your guest list.

If you want to see some family-friendly attractions in the area, you have plenty of choice. Maui Ocean Center, Hawaiian Islands Humpback Whale Sanctuary Visitor Center and Maui Fish Pipe promise lots of fun for all ages.

Are there one-bedroom vacation rentals in or near Wailea?

Often located in prime positions due to their smaller size, a one-bedroom vacation rental is the perfect solution if it's just the two of you. Here's a taste of Vrbo's range in or near Wailea:

  • Take a sneak peek at Luxurious Tropical Retreat Wailea Ekahi Unit, a great centrally located one-bedroom vacation property. A restaurant dining guide and a barbecue grill are just two of the amenities included here.
  • Or maybe Luxury Cottage With Private Pool. Under The Warm Maui Sun Pmt #bbkm2016004 is a better match. Another central one-bedroom option, this place has high-speed internet services, a fridge and much more.

Can I find two-bedroom vacation rentals in or near Wailea?

You sure can! From swish apartments to cute cottages, Vrbo offers a selection of vacation rentals. Traveling families will appreciate these two-bedroom options in or near Wailea:

  • Leading our list is The Maui Escape - Spectacular 2. 5 Bdr Penthouse. This two-bedroom delight offers its guests handy amenities like a fridge and off-street parking options. Visit Wailea's excellent attractions from this comfortable base.
  • Owner Direct Read Our Guest Reviews Elua Village 701 is another popular two-bedroom retreat. It has beach sun loungers, off-street parking options and lots more.

What are the best three-bedroom vacation rentals in or near Wailea?

Three-bedroom rentals in or near Wailea give you both space and freedom to enjoy your vacation. Take a peek at some of the fantastic options available here:

  • Offering the trifecta of comfort, privacy and space, you'll get the whole gang's nod of approval at Ocean View, Close To Beach And Pool. This retreat comes with many handy amenities, including a TV and a barbecue grill.
  • Another popular three-bedroom rental is Privatehome 3b/3b Spectacular Bi. Make use of a fridge and high-speed internet services while spending precious time with those close to you.