Find Vacation Rentals in Wailea

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Popular Wailea Vacation Rentals

Find the perfect Wailea vacation rental

Condo Wailea
$399 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (75 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$383 per night
Condo ∙ 8 guests ∙ 3 bedrooms
3.5
Good (65 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
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Details
Condo Wailea
$560 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (9 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Villa Wailea
$915 per night
Villa ∙ 10 guests ∙ 3 bedrooms
4.8
Outstanding (58 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
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Details
Condo Wailea
$480 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (3 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
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Details
Condo Wailea
$447 per night
Condo ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (3 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$246 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.6
Excellent (70 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$382 per night
Condo ∙ 5 guests ∙ 2 bedrooms
4.8
Outstanding (162 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$252 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding (73 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
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Vacation Homes With Terraces

Condo  Wailea
$376 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding (30 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Details
Vrbo
Details
Details
Condo  Wailea
$200 per night
Condo ∙ 2 guests ∙ 1 bedroom
4.9
Outstanding (156 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Details
Vrbo
Details
Details
Condo  Wailea
$462 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (89 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Details
Vrbo
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Vacation rentals and apartments with air conditioning

Condo  Wailea
$293 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.7
Excellent (65 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Details
Vrbo
Details
Details
Condo  Wailea
$245 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.1
Very good (26 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Details
Vrbo
Details
Details
Condo  Wailea
$243 per night
Condo ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (78 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Details
Vrbo
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Apartments and vacation rentals with a kitchen

Condo  Wailea
$303 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
Details
HomeToGo
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Details
Condo  Wailea
$209 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.8
Outstanding (68 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
Details
Vrbo
Details
Details
Condo  Wailea
$253 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.4
Very good (81 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
Details
Vrbo
Details
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 $202 per night.

Is it possible to compare several vacation rentals in Wailea?

At the moment there are 5,219 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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