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Wailea Vacation Rentals

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Recommended Vacation Rentals in Wailea

Find your perfect vacation rental in Wailea: from $341 per night

House Wailea
May 24 - May 31
House ∙ 6 guests ∙ 3 bedrooms

House

Wailea, Wailea-Makena, Hawaii, United States
$744
per night
Very good(30 ratings)
$744
per night
View deal
House Wailea
-27%
Jun 7 - Jun 14
House ∙ 8 guests ∙ 3 bedrooms

307 m² House

Wailea, Wailea-Makena, Hawaii, United States
$2,641$1,930
per night
Outstanding(153 ratings)
$2,641$1,930
per night
View deal
Serviced apartment Wailea
-25%
Apr 24 - May 1
Serviced apartment ∙ 127 guests ∙ 3 bedrooms

1200 m² Serviced apartment

Wailea, Wailea-Makena, Hawaii, United States
$422$316
per night
Very good
$422$316
per night
View deal
Condo Wailea
Apr 6 - Apr 13
Condo ∙ 6 guests ∙ 3 bedrooms

204 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$2,438
per night
Outstanding(154 ratings)
$2,438
per night
View deal
House Wailea
Apr 5 - Apr 12
House ∙ 6 guests ∙ 3 bedrooms

93 m² House

Wailea, Wailea-Makena, Hawaii, United States
$953
per night
Excellent(62 ratings)
$953
per night
View deal
Villa Wailea
-30%
Nov 30 - Dec 7
Villa ∙ 10 guests ∙ 4 bedrooms

307 m² Villa

Wailea, Wailea-Makena, Hawaii, United States
$2,761$1,939
per night
Outstanding(38 ratings)
$2,761$1,939
per night
View deal
House Wailea
Dec 7 - Dec 14
House ∙ 8 guests ∙ 4 bedrooms

382 m² House

Wailea, Wailea-Makena, Hawaii, United States
$3,597
per night
Outstanding(126 ratings)
$3,597
per night
View deal
Condo Wailea
May 24 - May 31
Condo ∙ 4 guests ∙ 2 bedrooms

76 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$507
per night
Outstanding(28 ratings)
$507
per night
View deal
House Wailea
-7%
May 24 - May 31
House ∙ 6 guests ∙ 3 bedrooms

143 m² House

Wailea, Wailea-Makena, Hawaii, United States
$1,320$1,223
per night
Outstanding(109 ratings)
$1,320$1,223
per night
View deal
Condo Wailea
Nov 30 - Dec 7
Condo ∙ 5 guests ∙ 3 bedrooms

112 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$801
per night
Outstanding(44 ratings)
$801
per night
View deal
Villa Wailea
Apr 5 - Apr 12
Villa ∙ 10 guests ∙ 4 bedrooms

322 m² Villa

Wailea, Wailea-Makena, Hawaii, United States
$1,989
per night
Outstanding(155 ratings)
$1,989
per night
View deal
House Wailea
May 24 - May 31
House ∙ 8 guests ∙ 3 bedrooms

325 m² House

Wailea, Wailea-Makena, Hawaii, United States
$2,263
per night
Outstanding(87 ratings)
$2,263
per night
View deal
Condo Wailea
Dec 7 - Dec 14
Condo ∙ 6 guests ∙ 3 bedrooms

110 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$991
per night
Excellent(23 ratings)
$991
per night
View deal
Condo Wailea
-7%
Apr 5 - Apr 12
Condo ∙ 6 guests ∙ 2 bedrooms

139 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$488$454
per night
Outstanding(135 ratings)
$488$454
per night
View deal
House Wailea
-8%
May 24 - May 31
House ∙ 13 guests ∙ 4 bedrooms

223 m² House

Wailea, Wailea-Makena, Hawaii, United States
$2,716$2,507
per night
Outstanding(70 ratings)
$2,716$2,507
per night
View deal

Vacation rentals and apartments with air conditioning

Condo  Wailea
Apr 5 - Apr 12
-33%
$423
$283 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.7
Excellent(189 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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House  Wailea
May 24 - May 31
-19%
$973
$790 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(33 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Villa  Wailea
Nov 19 - Nov 26
$1,965 per night
Villa ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding(52 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Apartments with a balcony or patio

Condo  Wailea
Dec 3 - Dec 10
-42%
$652
$380 per night
Condo ∙ 4 guests ∙ 1 bedroom
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
Dec 7 - Dec 14
-29%
$785
$556 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(62 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
Dec 7 - Dec 14
$594 per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(107 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
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Cabins with a sauna

Condo  Wailea
Aug 23 - Aug 30
-22%
$853
$670 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
Sauna
View deal
Condo  Wailea
Dec 7 - Dec 14
$694 per night
Condo ∙ 5 guests ∙ 3 bedrooms
4.8
Outstanding(23 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Sauna
View deal
Condo  Wailea
Apr 5 - Apr 12
-7%
$528
$490 per night
Condo ∙ 2 guests ∙ 2 bedrooms
4.9
Outstanding(93 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Sauna
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Best Vacation Home Deals in Wailea

Save up to 23%

Condo Wailea
Dec 7 - Dec 14
-4%
$741
$714 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(111 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
May 24 - May 31
-23%
$771
$592 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(68 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
Mar 2 - Mar 9
-4%
$1,361
$1,304 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(152 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Discover a vacation rental meeting your needs among the 7,293 great properties from 30 providers in Wailea. HomeToGo instantaneously compares all of these vacation homes so you can save up to 23%!

Budget-friendly Rentals in Wailea

Find Fantastic yet Inexpensive Rentals

Condo Wailea
Apr 5 - Apr 12
$669 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.7
Excellent(52 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
May 24 - May 31
$728 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding(68 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Apr 5 - Apr 12
$707 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent(45 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Top-Rated Offers and Accommodations in Wailea

Book Vacation Rentals with the Highest User Rating

Condo Wailea
May 24 - May 31
$1,056 per night
Condo ∙ 8 guests ∙ 4 bedrooms
4.8
Outstanding(103 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Apr 5 - Apr 12
$1,200 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.8
Outstanding(28 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Apr 5 - Apr 12
$523 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.8
Outstanding(26 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Customer ratings and reviews

How are reviews collected?
Guest
Guest verified by HomeToGo

Great place, everything you need and want for you stay. Living area and Master bedroom views great.

Reviewed on 9/25/2024 | Group
Condo Wailea
from $1,468 per night
HomeToGo
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(48 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
from $1,468 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(48 ratings)
Wailea, Wailea-Makena, Hawaii, United States
HomeToGo
View deal
Guest
Guest verified by HomeToGo

We loved this condo for our family of four (2 teenage boys). It had enough space for us to spread out. The location is perfect! Easy access to the beach, town and the most amazing spot to watch the sunset! Someone in the reviews mentioned road noise, I live in a rural quiet place and was a bit worried, but it was not an issue at all!

Reviewed on 10/30/2023 | Family
Condo Wailea
from $574 per night
HomeToGo
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(108 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
from $574 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(108 ratings)
Wailea, Wailea-Makena, Hawaii, United States
HomeToGo
View deal
Guest
Guest verified by HomeToGo

A great clean affordable option for a week away. Many options within walking distance and everything you need to enjoy your stay is supplied.

Reviewed on 10/27/2023 | Couple
Condo Wailea
from $354 per night
HomeToGo
Condo ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(94 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
from $354 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(94 ratings)
Wailea, Wailea-Makena, Hawaii, United States
HomeToGo
View deal

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Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Wailea

  • Pool (6,143)
  • WiFi (7,296)
  • Air conditioning (6,684)
  • Balcony/patio (2,161)
  • Kitchen (6,670)
  • Parking (308)
  • Washing machine (5,278)
  • TV (6,754)
  • Dishwasher (4,551)
  • Grill (4,339)
  • Microwave (5,865)
  • Jacuzzi (1,194)

Finding a vacation rental with a pool shouldn't be too difficult in Wailea. Most of the properties offer one. Condo with pools in Wailea are a good choice for groups of 5 and usually cost around $1,145 a night. Among these rentals, 39 of them are situated within 2 kilometres of water.

Price and Availability Index in Wailea

Click on any bar to see price and availability information

Vacation Rental Price Information in Wailea

The graph shows the average rental prices for the next twelve months in Wailea. The most expensive prices are in January (1/25 – 2/1). Prices reach an average of $993 per night. Wailea is cheaper in a week of November (11/16 – 11/23), where prices are on average $676 a night.

Rental availability information in Wailea

The availability graph shows the percentage of available vacation rentals in Wailea. The week with the highest booking rate in the next 12 months is in September (9/20 – 9/27), where 86% of the vacation rentals are booked. Conversely, it is in May (5/10 – 5/17) that the highest percentage of vacation homes are available.

Experience the magic of Maui from your Wailea vacation home

Whether you choose a condo or villa as your Wailea vacation rental, you'll have the perfect base to explore the beauty of Maui.

Where are the unique attractions in Wailea?

Maui's best beaches

Wailea Beach is consistently rated as one of the best beaches in the world. A wide, crescent-shaped beach with golden sand, Wailea beach also has calm waters—making it perfect for snorkeling, paddle boarding, and swimming.

Set on Maui's southwestern shores, Makena Beach State Park offers a secluded alternative to some of the more crowded beaches. Also known as Big Beach, Makena Beach is dramatically set between two black lava outcroppings.

Information about vacation rentals in Wailea

🏡 Vacation rentals available 7,293 rentals
💳 Possible discounts up to 23%
🌙 Nightly prices starting at $341
⭐ Popular amenities Pool, Internet and Air conditioning
🏊 Vacation rentals with pools 5,895 homes
2 reviews
Wailea vacation rentals have an average rating of 3.5/5 on 2 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Wailea?

We found 7,293 vacation homes in Wailea available for your next trip.

What are the most popular vacation home amenities in Wailea?

Many travellers are searching for Pool, Internet, and Air conditioning when booking a vacation home in Wailea.

Are there pet-friendly vacation rentals in Wailea?

Yes, there are 239 pet-friendly vacation rentals in Wailea, with an average nightly price of $2,549.

What's the best month to visit Wailea?

When booking a vacation rental in Wailea, remember that the rainiest months are usually March and November, with January often being the sunniest.

Find the perfect Wailea home to match your style

Top cities to visit

Vacation Destinations Near Wailea

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