Wailea Vacation Rentals

Compare 9,250 available properties from 27 providers
Wailea
Anytime
2 guests
Save up to 39%

Best Vacation Home Deals in Wailea

-33%
e.g. 5/4 - 5/11
Apartment ∙ 5 guests ∙ 2 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
from $247 $370
VRBO
4.6
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-39%
e.g. 4/6 - 4/13
Apartment ∙ 6 guests ∙ 3 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
from $307 $507
VRBO
4.1
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-28%
e.g. 9/14 - 9/21
Apartment ∙ 2 guests ∙ 1 bedroom
Wailea, Wailea-Makena, Hawaii, United States
from $505 $698
VRBO
5.0
View deal

Book a welcoming vacation rental from $115 per night by searching through the 9,250 options listed in Wailea. Using HomeToGo you can immediately compare the prices of each listed rental to find the best price and save up to 39%.

Recommended Vacation Rentals in Wailea

Find your perfect vacation rental in Wailea: from $116 per night

Apartment ∙ 2 guests
Wailea, Wailea-Makena, Hawaii, United States
from $161
VRBO
4.9
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Apartment ∙ 2 guests ∙ 1 bedroom
Wailea, Wailea-Makena, Hawaii, United States
from $378
VRBO
4.7
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Apartment ∙ 4 guests ∙ 2 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
from $323
VRBO
4.8
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Apartment ∙ 4 guests ∙ 2 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
from $286
VRBO
4.9
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House ∙ 4 guests ∙ 1 bedroom
Wailea, Wailea-Makena, Hawaii, United States
from $221
VRBO
4.9
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House ∙ 4 guests ∙ 2 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
from $273
VRBO
5.0
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House ∙ 5 guests ∙ 2 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
from $255
Booking.com
5.0
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House ∙ 5 guests ∙ 2 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
from $264
Booking.com
5.0
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House ∙ 6 guests ∙ 3 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
from $269
Booking.com
4.5
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Vacation Houses With Pools

Pool
Apartment ∙ 4 guests ∙ 1 bedroom
Wailea, Wailea-Makena, Hawaii, United States
from $239
VRBO
4.3
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Pool
Apartment ∙ 4 guests ∙ 2 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
from $260
VRBO
4.6
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Pool
Apartment ∙ 4 guests ∙ 1 bedroom
Wailea, Wailea-Makena, Hawaii, United States
from $464
VRBO
4.9
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Vacation Homes With Fishing Spots Nearby

Fishing
Apartment ∙ 2 guests ∙ 1 bedroom
Wailea, Wailea-Makena, Hawaii, United States
from $1,216
VRBO
5.0
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Fishing
Apartment ∙ 4 guests ∙ 1 bedroom
Wailea, Wailea-Makena, Hawaii, United States
from $171
VRBO
4.8
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Fishing
Apartment ∙ 4 guests ∙ 2 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
from $212
VRBO
4.6
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Apartments With Balconies or Patios

Balcony/Patio
Apartment ∙ 4 guests ∙ 1 bedroom
Wailea, Wailea-Makena, Hawaii, United States
from $459
VRBO
4.4
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Balcony/Patio
Apartment ∙ 4 guests ∙ 2 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
from $179
VRBO
4.9
View deal
Balcony/Patio
Apartment ∙ 6 guests ∙ 2 bedrooms
Wailea, Wailea-Makena, Hawaii, United States
from $247
VRBO
5.0
View deal
See all offers

Popular Rental Amenities in Wailea

  • Kitchen (1,713)
  • Internet (1,480)
  • Pool (1,429)
  • TV (1,412)
  • Washer (1,249)
  • AC (1,245)
  • Grill (1,163)
  • Microwave (1,151)
  • No smoking (1,082)
  • Dishwasher (1,063)
  • Parking (856)
  • No pets (850)
Above, you can find the most commonly chosen filters in Wailea and the number of rentals that have them. Wailea is the right place to book a rental if you want to tune out with some TV time or you can't imagine a vacation without internet, as the most common features are "TVs" and "internet." Three features that are not often provided are "fireplaces," "Pets Allowed," and "saunas."

Price and Availability Index in Wailea

Vacation Rental Price Information in Wailea

We analyzed vacation houses, cottages and apartments to display a price graph showing the average price per night in Wailea. Prices rise in February and reach an average of $385 a night (2/8 - 2/15), making it the most expensive time to book a rental in the next 12 months. Conversely, the cheapest average prices are in a week of July (7/20 - 7/27).

Rental Availability Information in Wailea

The availability graph shows the percentage of available rentals in Wailea. It is harder to find an accommodation during a week of December (12/21 - 12/28), as 75% of the rentals are booked. It will be easy to find a rental that suits you in a week of August (8/24 - 8/31), as 86% of the rentals are still available.

The Weather in Wailea

81°
63°
82°
64°
82°
64°
84°
68°
86°
68°
88°
70°
88°
72°
90°
73°
90°
72°
88°
70°
84°
68°
82°
66°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Above are the weather conditions for Wailea. August is the warmest month of the year in Wailea with temperatures reaching a maximum average of 89°. Conversely, January is the coolest month in Wailea, with temperatures going under 62° The rainiest month is March while the driest month is January.

Accommodations in Wailea

1,188 of the 9,250 listed properties in Wailea are apartment rentals. They account for many of the accommodation types in this destination (62.69%). Interestingly, the average rental fee for this type of accommodation in particular is $436 a night, with an average size of 1,020 ft². Furthermore, these rentals are perfect for 5 it represents the average number of vacationers apartment rentals can host in Wailea. House rentals are the other most common type of accommodation in Wailea. While apartment rentals in Wailea have an average size of 1,020 ft², house rentals have an average size of 2,030 ft².

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.

Show all 9,250 properties
Food & Drinks

Hawaiian food with foreign flair

Monkeypod Kitchen has a fun atmosphere with two happy hours each day. They serve up bar classics, such as pizza and burgers, as well as food with a Hawaiian twist, such as poke tacos and lobster deviled eggs. They also offer many vegetarian options that also can be made vegan upon request.

KO Restaurant offers fresh, delicious takes on Maui cuisine with a contemporary flair. Their menu includes influences from Hawaiian, Chinese, Japanese, Korean, Filipino, American, and Portuguese cuisine, making for unique and distinctive flavors.

Family Activities

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.

Local Attractions

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.

We compare more than 600 providers, including:

Booking.com Vacation Rentals in Wailea VRBO Vacation Rentals in Wailea HomeAway Vacation Rentals in Wailea Airbnb Vacation Rentals in Wailea TripAdvisor Vacation Rentals in Wailea VacationRentals.com Vacation Rentals in Wailea HouseTrip Vacation Rentals in Wailea FlipKey Vacation Rentals in Wailea 9flats.com Vacation Rentals in Wailea VaycayHero Vacation Rentals in Wailea PerfectPlaces.com Vacation Rentals in Wailea Homestay.com Vacation Rentals in Wailea Only-apartments Vacation Rentals in Wailea Interhome Vacation Rentals in Wailea Bedycasa Vacation Rentals in Wailea Novasol Vacation Rentals in Wailea HomeEscape Vacation Rentals in Wailea

Vacation Destinations Near Wailea