Wailea vacation rentals

We found 1,416 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Wailea by choosing from 63 houses, 46 apartments, and other vacation rentals. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the amenities you need and want, which might include parking and a fireplace. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.
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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.

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.

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.

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.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Wailea?
The most popular types of vacation rentals in Wailea are condos. Want something different? Vrbo has a variety of options to match our guests’ unique needs, so you’ll see properties in all sizes, and for all budgets. The perfect home away from home is waiting for you — get hold of yours today.
How much does it cost to rent a vacation rental in Wailea?
Different factors can influence the price of a vacation rental in Wailea, like the season, length of stay and type of property. But, all Vrbo homes have one thing in common — exceptional value. Just add your travel dates to find your perfect match.
How much does it cost to rent a beach house in Wailea?
The average price for a vacation rental near the beach in Wailea will depend on when you’re going and the size and style of property you’re searching for. You can easily find prices on Vrbo by entering your preferred travel dates. Then use our filter tool to pick the number of bedrooms and amenities important to you, like WiFi, a pool and air conditioning.
Are there pet-friendly vacation rentals in Wailea?
Pack a suitcase for your pooch because Wailea has 847 properties that throw open their doors to pets. Let your four-legged pal join in with the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates then check the “Pets allowed” filter box.
Can I rent a house with a pool in Wailea?
Grab your swimsuit and inflatable unicorn, because there are 764 houses with a private pool in Wailea. Settle in at one of these popular vacation rentals and you’ll enjoy pool days every day. Simply enter your travel dates into Vrbo, then check the “pool” filter to find the perfect place for a splashing good time!
What are popular rental amenities in Wailea?
The most popular rental amenities people prefer in Wailea include a beach view, a swimming pool and an electric car charging station. Whether you’re on the road with pals, family or even pets, Vrbo vacation homes feature the best amenities for making new memories with the people that matter most.
Are there large group vacation rentals in Wailea?
Choose from 41 vacation homes in Wailea that can sleep 10 or more guests. Whether you’re planning a get-together with extended family or an event like a party, there’s ample space to get your favorite people together under one roof.
Are there vacation rentals in Wailea that welcome kids?
Wailea has 845 family-friendly vacation rentals. And booking a stay that welcomes kiddos is simple with our “Properties good for families” filter. Besides having the whole place to yourselves, you’ll also get conveniences and perks such as multiple bedrooms, kitchens and private pools.
What are the top attractions for families in Wailea?
Keeping the kids entertained during your Wailea vacation is a breeze with these top family-friendly attractions:

  • Po’olenalena Beach
  • Ulua Beach
  • Ahihi Kinau Natural Area Reserve

Are there one-bedroom vacation rentals in Wailea?
There are 267 one-bedroom properties in Wailea to choose from. A one-bedroom vacation property is an excellent option if it’s just the two of you or if you’re traveling on your own. Throw in more space, privacy and convenience than a hotel, and you’ve got the makings of a trip to remember.
Can I find two-bedroom vacation rentals in Wailea?
Wailea has 383 two-bedroom vacation properties for you to select from. Find a vacation home with all the privacy and comfort you need at a price that’s hard to resist on Vrbo.
Are there vacation rentals with WiFi in Wailea?
Whether you’d like to keep up with the latest news, send a few emails or update your social media, there are 465 vacation homes with WiFi in Wailea. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Wailea?
Select your dates and then use our filters to see vacation rentals with ac in Wailea on Vrbo. With 806 air-conditioned properties available here, you can look forward to a cool and comfortable break.
How old do you have to be to rent a vacation rental in Wailea?
The minimum age is usually 16, 18 or 21. It can vary from one property to another on Vrbo, so look at the rules of your preferred Wailea stay before making a booking.
How long can I rent a vacation rental in Wailea for?
The length of time you can rent a vacation rental in Wailea varies according to the property. Just enter your preferred travel dates to look at a list of options offering extended stays. With loads of creature comforts such as washing machines and air conditioning, as well as some offering weekly or monthly discounts, you’re sure to get the perfect place to call your home away from home in Wailea.
Does Vrbo offer discounts for vacation homes in Wailea?
In Wailea, you’ll find amazing discounts and deals for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re planning a mini vacay or a few weeks away, we have a host of options to suit your style.

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