Find Vacation Rentals in Wailea

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Popular Wailea Vacation Rentals

Find the perfect Wailea vacation rental

House Wailea
from $350 per night
15 guests ∙ 5 bedrooms

House

Wailea, Wailea-Makena, Hawaii, United States
Details
Condo Wailea
from $1,681 per night
Condo ∙ 8 guests ∙ 4 bedrooms

307 m² Condo

4.7
Excellent(50 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Condo Wailea
from $356 per night
Condo ∙ 4 guests ∙ 2 bedrooms

112 m² Condo

5.0
Outstanding(74 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
House Wailea
from $1,147 per night
House ∙ 10 guests ∙ 4 bedrooms

251 m² House

5.0
Outstanding(100 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Villa Wailea
from $1,123 per night
Villa ∙ 9 guests ∙ 4 bedrooms

279 m² Villa

5.0
Outstanding(125 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Condo Wailea
from $187 per night
Condo ∙ 2 guests ∙ 1 bedroom

37 m² Condo

4.9
Outstanding(110 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Condo Wailea
from $291 per night
Condo ∙ 6 guests ∙ 2 bedrooms

97 m² Condo

5.0
Outstanding(4 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Condo Wailea
from $242 per night
6 guests ∙ 2 bedrooms

Condo

5.0
Outstanding(3 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Serviced apartment Wailea
from $216 per night
Serviced apartment ∙ 6 guests ∙ 2 bedrooms

1200 m² Serviced apartment

4.0
Very good
Wailea, Wailea-Makena, Hawaii, United States
Details
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Vacation rentals and apartments with air conditioning

Cabin  Wailea
from $297 per night
5 guests ∙ 2 bedrooms

Cabin

4.6
Excellent(44 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Details
House  Wailea
from $526 per night
House ∙ 8 guests ∙ 3 bedrooms

139 m² House

Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Details
Condo  Wailea
-39%
$782
from $504 per night
Condo ∙ 6 guests ∙ 2 bedrooms

75 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Details
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Apartments and vacation rentals with a kitchen

Condo  Wailea
from $284 per night
Condo ∙ 4 guests ∙ 2 bedrooms

76 m² Condo

4.8
Outstanding(33 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
Details
Condo  Wailea
from $1,199 per night
Condo ∙ 8 guests ∙ 3 bedrooms

123 m² Condo

5.0
Outstanding(118 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
Details
Condo  Wailea
from $481 per night
Condo ∙ 8 guests ∙ 3 bedrooms

129 m² Condo

4.8
Outstanding(102 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
Details
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Vacation rentals with Wi-Fi

Condo  Wailea
from $515 per night
Condo ∙ 6 guests ∙ 2 bedrooms

83 m² Condo

4.9
Outstanding(22 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
Details
Condo  Wailea
from $231 per night
Condo ∙ 3 guests ∙ 1 bedroom

58 m² Condo

4.9
Outstanding(48 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
Details
Condo  Wailea
from $511 per night
Condo ∙ 8 guests ∙ 3 bedrooms

129 m² Condo

4.9
Outstanding(32 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
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 $186 per night.

Is it possible to compare several vacation rentals in Wailea?

At the moment there are 6,419 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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