Find Vacation Rentals in Wailea

We have 5,653 properties to choose from
Wailea
Anytime
Guests
Wailea
Anytime
Guests

Popular Wailea Vacation Rentals

Find the perfect Wailea vacation rental

Condo Wailea
$319 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (66 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vacasa
Details
Details
House Wailea
$733 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (149 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$432 per night
Condo ∙ 8 guests ∙ 3 bedrooms
4.4
Very good (16 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
House Wailea
$1,053 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding (99 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
House Wailea
$1,997 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (37 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$330 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (95 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$558 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (60 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$928 per night
Condo ∙ 5 guests ∙ 2 bedrooms
4.9
Outstanding (98 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$1,742 per night
Condo ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (31 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
View more

Vacation rentals and apartments with air conditioning

Condo  Wailea
$309 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (66 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Details
Vrbo
Details
Details
Condo  Wailea
$648 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent (69 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Details
Vacasa
Details
Details
Condo  Wailea
$528 per night
Condo ∙ 9 guests ∙ 3 bedrooms
4.7
Excellent (95 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Details
Vrbo
Details
Details
View more

Vacation Homes With Terraces

Condo  Wailea
$348 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (62 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Details
Vrbo
Details
Details
Condo  Wailea
$346 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding (27 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Details
Vacasa
Details
Details
Condo  Wailea
$166 per night
Condo ∙ 2 guests ∙ 1 bedroom
4.9
Outstanding (90 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Details
Vrbo
Details
Details
View more

Apartments and vacation rentals with a kitchen

Condo  Wailea
$569 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (27 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
Details
Vacasa
Details
Details
Cottage  Wailea
$305 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
4.8
Outstanding (40 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
Details
Vacasa
Details
Details
Condo  Wailea
$313 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.1
Very good (16 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
Details
Vacasa
Details
Details
View more

Frequently Asked Questions

How much does it cost to stay in Wailea?

Vacation rentals in Wailea are priced starting at $167 per night.

Is it possible to compare several vacation rentals in Wailea?

At the moment there are 5,653 vacation rentals available for you to choose from.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Maui Meadows Information

About Maui

Maui is a tropical paradise with many of the United States' most scenic and certainly warmest beaches. Though that is not all you will find in Hawaii's second largest island. With epic volcanoes, Maui's wilderness is just as exciting as its baby blue waters. The variety of activities Maui offers is what makes Maui such a popular destination. West Maui is definitely the most commonly visited and therefore most developed coast, full of resorts, hotels, and vacation rentals, though in any of the regions in Maui you can find beautiful places to stay and things to do.

Things to Do in Maui

Ah the beaches: Keawakapu Beach, Napili Beach and Ka'anapali Beach are only three mentions but there are countless more. Apart from the usual sun bathing activities, Maui is chalk full of canoe, surfing and snorkel opportunities. In the winter, humpback whales migrate right up to the coast; seeing them is worth the extra cost of flying during the high tourist season. Golf courses speckle the island so decide on your destination then take your pick of at least two golf courses being driving if not walking distance from your Maui vacation rental. Haleakala National Park and Iao Valley State Monument have unreal hiking trails going through waterfalls and up to crater peaks. A drive on The Road to Hana is a spectacular road along sea cliffs and Wainapanapa State Park waits at the end.

Maui Accommodations

Lahaina is the big city in West Maui; the royals used to live there and as long as you don't mind the resorts, a Lahaina vacation rental will certainly make you feel like one. After you drive east on The Road to Hana, find a great rental in Hana to rest and wow over the drive. Book a Wailea rental in South Maui for more beaches and golf courses. Remember, no matter where you are, you can pretty much get anywhere on the island on a solid day trip.

Popular Day Trips Near Wailea

Show more
image-tag