Discover a selection of 4,000 vacation rentals in Wailea, HI, US 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 pool and air conditioning. Prices start at C$ 303 per night, and condo and apartment rentals and villa rentals are popular options for a stay in Wailea. Either way, you'll find a rental for everyone's needs.
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Destination guide

Like your personal space? Then you'll love Wailea

Wailea's the kind of place where folk just love a bit of elbow-room. Spread across 1,500 acres along Maui's south coast, Wailea vacation rentals are hands-down one of the most opulent ways to enjoy some quality time on the Valley Isle. If your idea of the perfect vacation is kicking back on golden-sand beaches, wheeling out your clubs for a few rounds on a championship golf course, indulging in some spa treatments, and sipping a Mai Tai on the terrace of a luxury condo, then you might as well stop your search right here, because Wailea is the one for you.

Things to do

Hop in your car and head way out in Wailea

Tearing yourself away from Wailea vacation rentals can be tricky, but Maui's got a whole host of adventures in store. The flagship excursion is a road trip out into Haleakala National Park. It's centred around the island's main volcano, and sunrises here are so popular that you'll need to book a spot in advance. And to soak up a bit of culture along with all that sunshine, try a trip to the historic whaling village of Lahaina, check out the former mission at the Bailey House Museum, or take in events and exhibitions at the Maui Arts and Cultural Center.

Activities

Strap on your snorkel and dive right on in

Slather on the sunscreen, because the beaches take centre stage with Wailea vacation rentals. Soak up a bit of sun on the golden sands, snorkel with the turtles, or take a trip out to do some whale-watching. And chances are you'll see plenty of golf bags coming off the carousel at Kahului Airport, with 3 championship courses on offer. Wailua's spa central too, and if you're looking to top off all that relaxation with a little retail therapy, then the Shops at Wailea complex has more than 70 shops, galleries, and restaurants to help you give your wallet a workout.

Weather

Wailea weather's a cut above the best, never mind the rest

For an island that you can drive across in less than 3 hours, Maui's got a whole load of different microclimates – mainly thanks to its volcanic landscapes and strong trade winds. And the good news for you is that Wailea has pretty much the best weather of the lot. Set on the sheltered south coast, it's warm and reasonably humid year-round, and while winter (November–April) does tend to bring a few more rain showers, they rarely last long. A Wailea vacation is a good opportunity to do a bit of whale-watching, with humpbacks passing on the migration between December and April.

Natural features

You'll fall in "lava" with this volcanic paradise

Wondrous Wailea's set on the south coast of Maui – Hawaii's second-largest island. Mention Maui to anyone who's been there before, and they're likely to drift off into a reverie of golden beaches, unspoiled rainforests, and impossibly grand volcanic landscapes. And that's before you venture into the water. With marine sanctuaries galore, these immaculate coral reefs teem with marine life, and local celebrities include the sea turtles and the migrating humpback whales. Most of Maui is formed of a massive shield volcano called Haleakala, and its eponymous national park incorporates 30,000 acres and a number of endangered species.

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.

Can I find a vacation rental around Wailea?

Yes, our 2021 property listings offer a large selection of 3,966 vacation rentals near Wailea. From 3,604 condo and apartment rentals to 104 villa rentals, 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 points of interest near where I can stay when traveling to Wailea?

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

  • Wailea Blue Golf Course: 4,216 vacation rentals
  • Wailea Gold Golf Course: 4,197 vacation rentals
  • Ulua Beach Park: 4,328 vacation rentals
  • Wailea Emerald Golf Course: 4,195 vacation rentals
  • Shops at Wailea: 4,317 vacation rentals

But there are many other points of interest around Wailea listed on Vrbo Canada 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 Canada has 3,604 Condos/Apartments in Wailea. Our other popular types of vacation rentals in Wailea include:

  • Villas: 104 rentals available
  • Houses: 305 rentals available
  • Resorts: 14 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 3,304 vacation rentals with pool available in Wailea. Please use our search bar to access the selection of vacation rentals available.