Find Vacation Rentals in Wailea

We have 3,733 properties to choose from
Wailea
Anytime
Guests

Popular Wailea Vacation Rentals

Find the perfect Wailea vacation rental

Condo Wailea
$185 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
"Excellent" (112 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$213 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.8
"Excellent" (113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$170 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
"Excellent" (157 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$220 per night
Condo ∙ 2 guests ∙ 1 bedroom
4.9
"Excellent" (104 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$226 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.8
"Excellent" (122 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$452 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (115 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$260 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
"Excellent" (31 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$231 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
"Excellent" (116 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
Condo Wailea
$237 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
"Excellent" (55 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
Vrbo
Details
Details
View more

Vacation rentals and apartments with air conditioning

Condo Air conditioning Wailea
$317 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
"Excellent" (134 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Details
Vrbo
Details
Details
Condo Air conditioning Wailea
$180 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
"Excellent" (92 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Details
Vrbo
Details
Details
Condo Air conditioning Wailea
$343 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
"Excellent" (85 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Details
Vrbo
Details
Details
View more

Vacation Homes With Terraces

Condo Balcony/Patio Wailea
$485 per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (98 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Details
Vrbo
Details
Details
Condo Balcony/Patio Wailea
$284 per night
Condo ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (130 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Details
Vrbo
Details
Details
Condo Balcony/Patio Wailea
$325 per night
Condo ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (80 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Details
Vrbo
Details
Details
View more

Vacation rentals with Wi-Fi

Condo Internet Wailea
$373 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.8
"Excellent" (9 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
Details
Vrbo
Details
Details
Condo Internet Wailea
$216 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
"Excellent" (129 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
Details
Vrbo
Details
Details
Condo Internet Wailea
$335 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (89 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
Details
Vrbo
Details
Details
View more

Frequently Asked Questions

How much does it cost to stay in Wailea?

Vacation rentals in Wailea are priced starting at $165 per night.

Is it possible to compare several vacation rentals in Wailea?

At the moment there are 3,733 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

image-tag