Wailea-Makena houses
We found 325 houses — enter your dates for availability
Explore Wailea-Makena house rentals
Makena Oceanfront 4 Bedroom/4 Bath Home - Captivating Views - Great Location
Sleeps 14 · 4 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
82 reviews(82 reviews)
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
142 reviews(142 reviews)
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
86 reviews(86 reviews)
~ This Is Wailea Living ~
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
120 reviews(120 reviews)
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
Sleeps 10 · 4 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
82 reviews(82 reviews)
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
74 reviews(74 reviews)
Top rated house rentals - Wailea-Makena
Family vacation
1010 out of 10
Exceptionalexceptional
58 reviews(58 reviews)
Amazing!
1010 out of 10
Exceptionalexceptional
88 reviews(88 reviews)
Perfect for families
1010 out of 10
Exceptionalexceptional
120 reviews(120 reviews)
Perfect
1010 out of 10
Exceptionalexceptional
62 reviews(62 reviews)
60th Birthday Celebration
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
5 Stars
1010 out of 10
Exceptionalexceptional
130 reviews(130 reviews)
Terrific Vacation House
1010 out of 10
Exceptionalexceptional
133 reviews(133 reviews)
Amazing
1010 out of 10
Exceptionalexceptional
82 reviews(82 reviews)
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Are there any vacation home rentals in Wailea-Makena?
Absolutely! You’ll discover 325 vacation home rentals around Wailea-Makena to select from. Whether you’re traveling to the popular city of Makena or somewhere else, we can help you find a property that checks every box on your list.
How much does it cost to stay in a vacation rental house in Wailea-Makena?
Whether you’re looking for a wallet-friendly getaway or a lavish retreat, Vrbo offers a variety of vacation home rentals in Wailea-Makena for you to choose from. Use our filter tools to compare prices and find the best place that meets your needs.
When is the best time to rent a vacation house in Wailea-Makena?
March is when most Vrbo guests book a vacation home rental in Wailea-Makena. Expect average temperatures of between 21ºC (70ºF) and 24ºC (75ºF) if you arrive during this month.
Where can I rent a Wailea-Makena vacation house with great views?
If you love to kick back and relax after a busy day, check out our vacation home rentals in Wailea-Makena that boast picturesque vistas like beach views.
Does Wailea-Makena have any weekend house rentals?
Explore our weekend rentals and get ready for a thrilling few days away. Our main tips for booking the perfect house in Wailea-Makena? Stay flexible when searching and modify your travel dates until you find the vacation home rental that fits your style.
Are there any pet-friendly house rentals in Wailea-Makena?
With 3 vacation home rentals in Wailea-Makena that welcome pets, going on a trip with the family dog is a cinch. Just use the filter tool to only show pet-friendly houses that typically come with perks like free dog treats and fenced backyards.
What are the top things to do in Wailea-Makena?
Head out and experience everything Wailea-Makena has to offer from the comfort of a vacation home rental. It pays to do a little research on the things you’d like to see and do, so you can plan the perfect escape.
Why should I book my vacation rental house with Vrbo?
From houses in quiet rural villages to those that’ll put you in the center of the action, Vrbo has a wide variety of vacation home rentals to pick from. One of the many great reasons to book with us? You won’t have to share your space with the owner or any other guests. And with flexible cancellation policies and support before, during and after your trip, we’ll make sure everything goes smoothly.