Find Vacation Rentals in Wailea

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Popular Wailea Vacation Rentals

Find the perfect Wailea vacation rental

House Wailea
from $333 per night
6 guests ∙ 3 bedrooms

House

4.2
Very good(30 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Vrbo
Details
House Wailea
from $2,018 per night
House ∙ 13 guests ∙ 4 bedrooms

223 m² House

5.0
Outstanding(70 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Vrbo
Details
House Wailea
from $1,266 per night
House ∙ 8 guests ∙ 3 bedrooms

307 m² House

5.0
Outstanding(153 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Vrbo
Details
House Wailea
from $717 per night
House ∙ 6 guests ∙ 3 bedrooms

143 m² House

5.0
Outstanding(108 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Vrbo
Details
Serviced apartment Wailea
from $172 per night
Serviced apartment ∙ 127 guests ∙ 3 bedrooms

1200 m² Serviced apartment

4.0
Very good
Wailea, Wailea-Makena, Hawaii, United States
Agoda
Details
House Wailea
from $1,048 per night
House ∙ 8 guests ∙ 4 bedrooms

307 m² House

4.9
Outstanding(100 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Vrbo
Details
House Wailea
from $819 per night
House ∙ 6 guests ∙ 3 bedrooms

214 m² House

5.0
Outstanding(151 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Vrbo
Details
Condo Wailea
from $393 per night
Condo ∙ 5 guests ∙ 3 bedrooms

112 m² Condo

4.9
Outstanding(44 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Vrbo
Details
Condo Wailea
from $1,487 per night
Condo ∙ 6 guests ∙ 3 bedrooms

204 m² Condo

5.0
Outstanding(154 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Vrbo
Details
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Apartments and vacation rentals with a kitchen

Condo  Wailea
from $405 per night
Condo ∙ 6 guests ∙ 2 bedrooms

88 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
Kitchen
HomeToGo
Details
Condo  Wailea
from $301 per night
Condo ∙ 6 guests ∙ 3 bedrooms

83 m² Condo

4.9
Outstanding(68 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
Vrbo
Details
Condo  Wailea
from $369 per night
Condo ∙ 6 guests ∙ 3 bedrooms

111 m² Condo

4.7
Excellent(45 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
Vrbo
Details
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Vacation rentals and apartments with air conditioning

Villa  Wailea
from $953 per night
Villa ∙ 10 guests ∙ 4 bedrooms

322 m² Villa

5.0
Outstanding(155 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Vrbo
Details
House  Wailea
from $717 per night
House ∙ 6 guests ∙ 3 bedrooms

143 m² House

5.0
Outstanding(109 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Vrbo
Details
Condo  Wailea
from $393 per night
Condo ∙ 5 guests ∙ 3 bedrooms

112 m² Condo

4.9
Outstanding(44 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Vrbo
Details
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Vacation Homes With Terraces

Cottage  Wailea
from $281 per night
5 guests ∙ 2 bedrooms

Cottage

4.8
Outstanding(41 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Vacasa
Details
Condo  Wailea
from $309 per night
6 guests ∙ 3 bedrooms

Condo

4.9
Outstanding(62 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Vrbo
Details
Condo  Wailea
from $339 per night
Condo ∙ 6 guests ∙ 3 bedrooms

98 m² Condo

5.0
Outstanding(107 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Vrbo
Details
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Frequently Asked Questions

How much does it cost to stay in Wailea?

Vacation rentals in Wailea are priced starting at $172 per night.

Is it possible to compare several vacation rentals in Wailea?

At the moment there are 7,711 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

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