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Wailea Vacation Rentals

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Top 15 Recommended vacation rentals in Wailea

Find your perfect vacation rental in Wailea from just $294 per night!

Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a heated pool, kitchen, balcony with mountain and sea views, and beach access for unforgettable stays.
from $388
per night
Outstanding(69 ratings)
from $388
per night
View deal
Apartment Wailea
Apartment ∙ 2 guests ∙ 1 bedroom

46 m² Apartment

Wailea, Wailea-Makena, Hawaii, United States
This Wailea apartment features a pool, Jacuzzi, balcony, and parking, perfect for a romantic getaway for two.
from $324
per night
Excellent(22 ratings)
from $324
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 1 bedroom

70 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a pool, kitchen, yard, jacuzzi, and parking, perfect for an unforgettable getaway with friends.
from $346
per night
Excellent(52 ratings)
from $346
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 2 bedrooms

79 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
This Kihei condo features a private pool, sauna, and fireplace, perfect for a family getaway just steps from the beach.
from $325
per night
Outstanding(85 ratings)
from $325
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

138 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
This Wailea-Makena condo features a pool, kitchen, yard, jacuzzi, balcony, mountain view, and parking for an unforgettable stay.
from $792
per night
Outstanding(55 ratings)
from $792
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

84 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
This Wailea-Makena condo features a private pool, balcony with mountain views, and a yard, perfect for family gatherings.
from $367
per night
Outstanding(90 ratings)
from $367
per night
View deal
House Wailea
House ∙ 12 guests ∙ 4 bedrooms

223 m² House

Wailea, Wailea-Makena, Hawaii, United States
This Wailea house rental features a private heated pool, kitchen, yard, and stunning mountain views, perfect for 12 guests.
from $2,247
per night
Outstanding(93 ratings)
from $2,247
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

112 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
This Kihei condo features a private pool, spa, and jacuzzi, perfect for families or groups of up to 8 seeking relaxation.
from $562
per night
Outstanding(85 ratings)
from $562
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

129 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo offers a pool, jacuzzi, balcony, and kitchen, perfect for families looking to relax and unwind.
from $864
per night
Outstanding(87 ratings)
from $864
per night
View deal
House Wailea
House ∙ 6 guests ∙ 2 bedrooms

1175 m² House

Wailea, Wailea-Makena, Hawaii, United States
This Wailea house rental features a pool, kitchen, and balcony, perfect for a getaway with family or friends.
from $407
per night
Excellent(71 ratings)
from $407
per night
View deal
House Wailea
House ∙ 5 guests ∙ 2 bedrooms

102 m² House

Wailea, Wailea-Makena, Hawaii, United States
This Wailea house rental features a kitchen, yard, balcony, and parking, perfect for families seeking a memorable getaway.
from $837
per night
Outstanding(36 ratings)
from $837
per night
View deal
Condo Wailea
Condo ∙ 7 guests ∙ 3 bedrooms

98 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a pool, kitchen, jacuzzi, and balcony, perfect for a getaway with up to seven guests.
from $399
per night
Outstanding(1 rating)
from $399
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

130 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a pool, kitchen, Jacuzzi, balcony, and parking, perfect for up to 8 guests seeking relaxation.
from $801
per night
Outstanding(122 ratings)
from $801
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

110 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
This Kihei condo features a heated pool, kitchen, and balcony, perfect for families seeking a memorable getaway.
from $669
per night
Excellent(114 ratings)
from $669
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

129 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo offers a pool, kitchen, jacuzzi, balcony, parking, and direct beach access for up to 8 guests.
from $658
per night
Outstanding(105 ratings)
from $658
per night
View deal

Apartments with a balcony or patio

Apartment  Wailea
from $298 per night
Apartment ∙ 4 guests ∙ 1 bedroom

60 m² Apartment

Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Cabin  Wailea
from $406 per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Cabin

4.6
Excellent(45 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
from $524 per night
Condo ∙ 8 guests ∙ 3 bedrooms

119 m² Condo

3.6
Good(68 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
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Vacation rentals and apartments with air conditioning

Condo  Wailea
from $1,060 per night
Condo ∙ 6 guests ∙ 2 bedrooms

75 m² Condo

4.0
Very good(2 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
from $446 per night
Condo ∙ 6 guests ∙ 3 bedrooms

97 m² Condo

5.0
Outstanding(171 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
from $396 per night
Condo ∙ 4 guests ∙ 2 bedrooms

72 m² Condo

4.9
Outstanding(91 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
See all offers

Best vacation rentals with a balcony

Condo  Wailea
from $356 per night
Condo ∙ 4 guests ∙ 1 bedroom

73 m² Condo

5.0
Outstanding(26 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
from $356 per night
Condo ∙ 4 guests ∙ 1 bedroom

82 m² Condo

4.9
Outstanding(69 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
from $383 per night
Condo ∙ 4 guests ∙ 1 bedroom

65 m² Condo

5.0
Outstanding(76 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
See all offers

Budget-friendly Rentals in Wailea

Find Fantastic yet Inexpensive Rentals

Condo Wailea
from $425 per night
Condo ∙ 6 guests ∙ 2 bedrooms

83 m² Condo

4.1
Very good(40 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
from $1,481 per night
House ∙ 6 guests ∙ 3 bedrooms

House

5.0
Outstanding(106 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $976 per night
Condo ∙ 6 guests ∙ 3 bedrooms

116 m² Condo

4.9
Outstanding(200 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
from $697 per night
Condo ∙ 6 guests ∙ 2 bedrooms

75 m² Condo

5.0
Outstanding(2 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $877 per night
Condo ∙ 6 guests ∙ 3 bedrooms

107 m² Condo

4.7
Excellent(186 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $99 per night
Condo ∙ 4 guests ∙ 1 bedroom

61 m² Condo

5.0
Outstanding(174 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Discover real guest reviews to help you choose the perfect stay in Wailea

How are reviews collected?
Robert M.
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 $1,949 per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(65 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Kerry H.
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 $620 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
David M.
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 $392 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(95 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

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

Popular Rental Amenities in Wailea

  • Pool (5,656)
  • WiFi (5,898)
  • Air conditioning (5,705)
  • Balcony/patio (2,566)
  • Kitchen (5,809)
  • Parking (273)
  • Washing machine (5,059)
  • TV (5,824)
  • Dishwasher (4,515)
  • Grill (4,419)
  • Microwave (4,982)
  • Jacuzzi (2,526)

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 $1,168 a night. Among these rentals, 38 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 December (12/26 – 1/2). Prices reach an average of $1,317 per night. Wailea is cheaper in a week of August (8/29 – 9/5), where prices are on average $1,114 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 February (2/21 – 2/28), where 70% of the vacation rentals are booked. Conversely, it is in July (7/18 – 7/25) 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.

What are the best activities for families in Wailea?

Ocean adventures for the whole family

Learn more about Hawaiian sea life with your family at the Maui Ocean Center, the top-rated aquarium of Hawaii. You don't need to get in the water to see live coral, sharks, turtles, and countless colorful fish. Aside from their many exhibits, they also offer educational tours and interactive presentations for a guided encounter with Hawaii's marine life.

For an even deeper ocean experience, travel a hundred feet below the surface with Atlantis Submarines. Their comfortable passenger vessels will carry your family under the sea in style, letting you observe sea life that's rarely seen by humans.

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 6,302 rentals
🌙 Nightly prices starting at $296
⭐ Popular amenities Pool, Internet and Air conditioning
🏊 Vacation rentals with pools 5,621 homes
12 reviews
Wailea vacation rentals have an average rating of 4.6/5 on 12 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Wailea?

We found 6,302 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 162 pet-friendly vacation rentals in Wailea, with an average nightly price of $2,907.

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.

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