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Condos in Wailea

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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Condo
Apartment
House
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

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.

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Save up to 32%

Best Vacation Home Deals in Wailea

Condo Wailea
Sep 30 - Oct 7
-22%
$193
$151 per night
Condo ∙ 4 guests ∙ 1 bedroom
Great Condo in Wailea with Large Pool + Ocean View
4.9
"Excellent" (157 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Sep 23 - Sep 30
-18%
$244
$200 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Wailea with Pool, Grill & Yard + Beach Nearby
4.8
"Excellent" (113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Sep 29 - Oct 6
-32%
$275
$188 per night
Condo ∙ 4 guests ∙ 1 bedroom
Pleasant Condo in Wailea with Pool & Grill + Close to Beach
4.9
"Excellent" (90 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Book a welcoming vacation rental from $148 per night by searching through the 3,721 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 32%.

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Top-Rated Rentals and Accommodations in Wailea

Condo Wailea
May 14 - May 21
-24%
$852
$645 per night
Condo ∙ 5 guests ∙ 2 bedrooms
Condo in Wailea with Main Pool + Panorama View
5.0
"Excellent" (87 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Aug 3 - Aug 10
$403 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Nice Condo in Wailea-Makena with Grill, Pool & Yard + Ocean Views
4.8
"Excellent" (82 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
May 21 - May 28
-18%
$601
$495 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Condo in Wailea with Private Garden + Ocean View
4.9
"Excellent" (74 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Recommended Vacation Rentals in Wailea

Find your perfect vacation rental in Wailea: from $148 per night

Condo Wailea
Sep 30 - Oct 7
-22%
$190
$151 per night
Condo ∙ 4 guests ∙ 1 bedroom
Great Condo in Wailea with Large Pool + Ocean View
4.9
"Excellent" (157 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Sep 23 - Sep 30
-18%
$244
$201 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Wailea with Pool, Grill & Yard + Beach Nearby
4.8
"Excellent" (113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Sep 10 - Sep 17
$187 per night
Condo ∙ 4 guests ∙ 1 bedroom
Lovely Condo in Wailea with Private Parking + Fabulous Views + Next to Beach
4.9
"Excellent" (31 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Sep 29 - Oct 6
-32%
$276
$189 per night
Condo ∙ 4 guests ∙ 1 bedroom
Pleasant Condo in Wailea with Pool & Grill + Close to Beach
4.9
"Excellent" (90 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Oct 7 - Oct 14
$175 per night
Condo ∙ 2 guests ∙ 1 bedroom
Wonderful Condo in Wailea-Makena with Large Garden + Garden View
4.9
"Excellent" (104 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Aug 20 - Aug 27
$158 per night
Condo ∙ 4 guests ∙ 1 bedroom
Beautiful Condo in Wailea with Botanical Garden + Next to Beach
4.9
"Excellent" (112 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Sep 10 - Sep 17
-48%
$476
$291 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Wailea with Updated Pool + Ocean Views
4.9
"Excellent" (85 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Aug 5 - Aug 12
-27%
$300
$220 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Wailea-Makena with Free Parking + Ocean View
5.0
"Excellent" (130 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Aug 26 - Sep 2
-39%
$326
$199 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Wailea-Makena with Grill, Yard & Pool + Beach Nearby
4.8
"Excellent" (126 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Wailea

Condo Wailea
Sep 23 - Sep 30
$179 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Wailea with Spacious Garden
4.9
"Excellent" (103 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Jul 26 - Aug 2
$285 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Kihei with Tropical Garden + Garden View + Close to Beach
5.0
"Excellent" (65 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Sep 18 - Sep 25
-21%
$379
$299 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Wailea-Makena with Yard, Grill & Pool
4.9
"Excellent" (103 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Wailea and book a vacation rental with air conditioning.

Condo Air conditioning Wailea
Sep 30 - Oct 7
-22%
$192
$150 per night
Condo ∙ 4 guests ∙ 1 bedroom
Great Condo in Wailea with Large Pool + Ocean View
4.9
"Excellent" (157 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Condo Air conditioning Wailea
Aug 20 - Aug 27
$157 per night
Condo ∙ 4 guests ∙ 1 bedroom
Beautiful Condo in Wailea with Botanical Garden + Next to Beach
4.9
"Excellent" (112 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Condo Air conditioning Wailea
Sep 9 - Sep 16
$300 per night
Condo ∙ 6 guests ∙ 1 bedroom
Condo in Wailea with Grill & Pool + Ocean Views
5.0
"Excellent" (7 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Apartments With Balconies or Patios

Looking for a home with a balcony? Check out these vacation homes in Wailea with their own private patios and balconies.

Condo Balcony/Patio Wailea
Sep 23 - Sep 30
-18%
$244
$200 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Wailea with Pool, Grill & Yard + Beach Nearby
4.8
"Excellent" (113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
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Condo Balcony/Patio Wailea
Sep 29 - Oct 6
-32%
$275
$188 per night
Condo ∙ 4 guests ∙ 1 bedroom
Pleasant Condo in Wailea with Pool & Grill + Close to Beach
4.9
"Excellent" (90 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
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Condo Balcony/Patio Wailea
Sep 10 - Sep 17
$187 per night
Condo ∙ 4 guests ∙ 1 bedroom
Lovely Condo in Wailea with Private Parking + Fabulous Views + Next to Beach
4.9
"Excellent" (31 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Wailea accommodation with high-speed internet.

Condo Internet Wailea
Jul 24 - Jul 31
$148 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Wailea with Yard, Grill & Pool + Panoramic View
4.8
"Excellent" (122 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
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Condo Internet Wailea
Aug 26 - Sep 2
-39%
$325
$199 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Wailea-Makena with Grill, Yard & Pool + Beach Nearby
4.8
"Excellent" (126 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
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House Internet Wailea
Sep 9 - Sep 16
$599 per night
House ∙ 7 guests ∙ 3 bedrooms
House in Wailea-Makena with Private Pool + Ocean View
4.8
"Excellent" (64 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
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Popular Rental Amenities in Wailea

  • Internet (5,540)
  • TV (5,276)
  • Pool (5,258)
  • Kitchen (5,152)
  • Microwave (5,089)
  • Air conditioning (5,032)
  • No pets (5,026)
  • No smoking (4,874)
  • Washer (4,592)
  • Dishwasher (4,425)
  • Grill (4,062)
  • Yard (2,847)

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 need internet access during your vacation or you never miss an episode of your favorite show, as the most common features are "Internet" and "TV." Three features that are not often provided are "Fireplace," "Parking," and "Sauna."

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 December and reach an average of $1,037 a night (12/23 - 12/30), 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 September (9/9 - 9/16).

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 April (4/1 - 4/8), as 81% of the rentals are booked. It will be easy to find a rental that suits you in a week of August (8/26 - 9/2), as 85% of the rentals are still available.

The Weather in Wailea

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63°
7 days 7
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64°
12 days 12
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70°
10 days 10
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72°
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73°
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66°
13 days 13
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 90°. Conversely, January is the coolest month in Wailea, with temperatures going under 63° The rainiest month is March while the driest month is January.

7-Day Weather Forecast in Wailea

Thu, 30 Mar
77°
77°

10%

4 h

7 mi/h

Fri, 31 Mar
78°
75°

5%

3 h

8 mi/h

Sat, 1 Apr
77°
75°

15%

3 h

3 mi/h

Sun, 2 Apr
75°
71°

15%

0 h

6 mi/h

Mon, 3 Apr
75°
73°

15%

0 h

5 mi/h

Tue, 4 Apr
77°
73°

10%

2 h

4 mi/h

Wed, 5 Apr
77°
75°

10%

1 h

6 mi/h

Accommodations for your vacation in Wailea

232 of the 3,739 listed properties in Wailea are house rental. They account for a few of the accommodation types in this destination (4.87%). Interestingly, the average rental fee for this type of accommodation in particular is $1,482 a night, with an average size of 204 m². Furthermore, these rentals are perfect for 7 it represents the average number of vacationers house rental can host in Wailea. Villa are the other most common type of accommodation in Wailea. While house rental in Wailea have an average size of 204 m², villa have an average size of 254 m².
Where to find the best food in Wailea?

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.

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 3,739 properties
💳 Possible discounts up to 39%
🌙 Nightly prices starting at $148
⭐ Popular amenities Internet, TV and Pool
🏊 Vacation rentals with pools 5,662 properties

Frequently Asked Questions

What is the typical price per night for a vacation rental in Wailea?

The price of a night's stay in Wailea starts at $148. If you would like to stay in a house rental, the average price is $1,482 per night. A villa Wailea will cost $2,591 per night on average.

How many vacation homes are available to book in Wailea?

Currently there are 3,739 vacation rentals available for booking for your trip.

What are the most popular amenities for vacation rentals in Wailea?

If you're looking to book a vacation rental in Wailea, others search for accommodation with these amenities: TV, Internet and Pool.

Are dogs allowed in vacation rentals in Wailea?

Finding a vacation home in Wailea that allows dogs is definitely possible, with 48 pet-friendly available.

What's the best month to travel to Wailea?

The warmest months in Wailea are August and September, with temperatures around 90 °F. January and February in Wailea are the coldest, with 63 °F on average.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Wailea TripAdvisor Vacation Rentals in Wailea Vrbo Vacation Rentals in Wailea VacationRentals.com Vacation Rentals in Wailea HouseTrip Vacation Rentals in Wailea FlipKey Vacation Rentals in Wailea Homestay.com Vacation Rentals in Wailea Only-apartments Vacation Rentals in Wailea Interhome Vacation Rentals in Wailea Novasol Vacation Rentals in Wailea HomeEscape Vacation Rentals in Wailea

Vacation Destinations Near Wailea

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