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Condos in Wailea

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Wailea
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$100 - $199
From $200
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Condo
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Apartment
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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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Best Vacation Home Deals in Wailea

Save up to 68%

Condo Wailea
Oct 24 - Oct 31
-68%
$839
$265 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Wailea with Tropical Garden + Pleasant Views
4.5
Excellent (80 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Nov 28 - Dec 5
-62%
$1,072
$406 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Wailea with Botanical Garden + Ocean View
5.0
Outstanding (6 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Villa Wailea
Sep 14 - Sep 21
-33%
$1,195
$796 per night
Villa ∙ 8 guests ∙ 3 bedrooms
Villa in Wailea with Grill, Sauna & Pool + Location View
4.9
Outstanding (38 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Book a welcoming vacation rental from $105 per night by searching through the 4,601 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 67%.

Top-Rated Rentals and Accommodations in Wailea

Book Vacation Rental Offers with the Highest User Rating

Condo Wailea
May 18 - May 25
-19%
$583
$471 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Condo in Kihei with Free Parking + Mountain Views
4.7
Excellent (154 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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House Wailea
Oct 24 - Oct 31
$1,199 per night
House ∙ 8 guests ∙ 4 bedrooms
Private House in Wailea with Pool, Yard & Grill
5.0
Outstanding (87 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Villa Wailea
Sep 14 - Sep 21
-34%
$1,198
$795 per night
Villa ∙ 6 guests ∙ 3 bedrooms
Villa in Wailea with Sauna, Pool & Grill + Ocean View + Beach Nearby
5.0
Outstanding (44 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Recommended Vacation Rentals in Wailea

Find your perfect vacation rental in Wailea: from $105 per night

Condo Wailea
Dec 1 - Dec 8
-18%
$190
$156 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Wailea with Large Pool
4.5
Excellent (108 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Apartment Wailea
Sep 21 - Sep 28
$200 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Apartment in Kihei with Grill & Pool
4.5
Excellent (37 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Oct 1 - Oct 8
-23%
$744
$575 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Wailea with Botanical Garden + Incredible View
4.8
Outstanding (44 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Dec 9 - Dec 16
-52%
$561
$270 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Wailea with Botanical Garden + Ocean View
4.2
Very good (86 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Dec 10 - Dec 17
-48%
$593
$309 per night
Condo ∙ 5 guests ∙ 2 bedrooms
Condo in Kihei with Botanical Garden + Oceanfront Views
4.4
Very good (60 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Oct 25 - Nov 1
-39%
$586
$355 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Wonderful Condo in Wailea with Botanical Garden + Ocean View
5.0
Outstanding (3 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Oct 20 - Oct 27
-56%
$741
$325 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Wailea-Makena with Lush Garden + Garden Views
5.0
Outstanding (34 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Villa Wailea
Jun 29 - Jul 6
$1,095 per night
Villa ∙ 10 guests ∙ 4 bedrooms
Villa in Wailea with Grill & Pool
5.0
Outstanding (26 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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House Wailea
Nov 11 - Nov 18
$591 per night
House ∙ 7 guests ∙ 3 bedrooms
Vacation Home in Wailea-Makena with Botanical Garden
4.7
Excellent (90 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Budget-friendly Vacation Rentals in Wailea

Find Fantastic yet Inexpensive Offers

Condo Wailea
Oct 10 - Oct 17
-40%
$499
$299 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Wailea with Grill, Pool & Yard + Wonderful View
4.8
Outstanding (107 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Jun 15 - Jun 22
$198 per night
Condo ∙ 4 guests ∙ 1 bedroom
Charming Condo in Wailea with Large Pool + Ocean View + Beach Nearby
4.9
Outstanding (194 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Sep 21 - Sep 28
-15%
$729
$619 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Condo in Wailea-Makena with Free Parking + Garden Views
4.5
Excellent (22 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 Wailea
May 18 - May 25
-22%
$449
$350 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Condo in Wailea with Botanical Garden + Volcano View
5.0
Outstanding (124 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Condo Wailea
Dec 7 - Dec 14
$569 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Condo in Wailea with Botanical Garden + Ocean View
4.4
Very good (12 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Apartment Wailea
May 18 - May 25
-18%
$130
$107 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Rental Apartment in Wailea-Makena with Yard & Pool + Close to Beach
4.8
Outstanding (229 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Wailea rental with full kitchen.

Condo Wailea
Nov 27 - Dec 4
$574 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Condo in Wailea with Grill, Pool & Yard + Ocean View + Next to Beach
4.3
Very good (67 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
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House Wailea
Nov 4 - Nov 11
-51%
$1,214
$601 per night
House ∙ 6 guests ∙ 3 bedrooms
Nice House in Wailea with Grill & Yard + Ocean Views
5.0
Outstanding (98 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
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Condo Wailea
Jul 5 - Jul 12
-33%
$425
$285 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Wailea with Oceanfront Pool + Ocean View
4.8
Outstanding (74 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
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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 Wailea
Jun 22 - Jun 29
$296 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Family Friendly Condo in Wailea with Botanical Garden + Ocean Views
3.5
Good (66 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
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Condo Wailea
Oct 15 - Oct 22
-28%
$440
$315 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Entire Condo in Wailea with Complimentary Parking + Ocean View
5.0
Outstanding (85 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
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Condo Wailea
Oct 21 - Oct 28
-35%
$335
$219 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Wailea with Grill, Yard & Pool
4.8
Outstanding (228 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
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Popular Rental Amenities in Wailea

  • Pool (4,279)
  • Air conditioning (4,256)
  • Kitchen (4,420)
  • Parking (263)
  • Balcony/patio (539)
  • WiFi (4,756)
  • Washing machine (4,010)
  • TV (4,550)
  • Microwave (4,338)
  • Dishwasher (3,821)
  • Grill (3,480)
  • No smoking (3,833)

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're dreaming of days spent poolside or you want to stay cool in your vacation home, as the most common features are "Pool" and "Air conditioning." Three features that are not often provided are "Wheelchair accessible," "Fireplace," and "Sauna."

Price and Availability Index in Wailea

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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 $819 a night (2/10 - 2/17), 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 August (8/31 - 9/7).

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 September (9/7 - 9/14), as 84% of the rentals are booked. It will be easy to find a rental that suits you in a week of June (6/22 - 6/29), as 79% of the rentals are still available.

The Weather in Wailea

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81°
63°
7 days 7
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64°
12 days 12
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13 days 13
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68°
11 days 11
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86°
68°
11 days 11
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88°
70°
10 days 10
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88°
72°
10 days 10
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90°
73°
10 days 10
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90°
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9 days 9
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88°
70°
9 days 9
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84°
68°
13 days 13
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82°
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, 28 Sep
82°
78°

10%

4 h

14 mi/h

Fri, 29 Sep
80°
78°

10%

5 h

7 mi/h

Sat, 30 Sep
80°
78°

10%

3 h

6 mi/h

Sun, 1 Oct
80°
78°

10%

4 h

5 mi/h

Mon, 2 Oct
82°
78°

10%

4 h

6 mi/h

Tue, 3 Oct
80°
78°

10%

6 h

7 mi/h

Wed, 4 Oct
78°
78°

10%

6 h

6 mi/h

Accommodations for your vacation in Wailea

137 of the 4,601 listed properties in Wailea are apartment rental. They account for a few of the accommodation types in this destination (4.46%). Interestingly, the average rental fee for this type of accommodation in particular is $654 a night, with an average size of 83 m². Furthermore, these rentals are perfect for 5 it represents the average number of vacationers apartment rental can host in Wailea. House rental are the other most common type of accommodation in Wailea. While apartment rental in Wailea have an average size of 83 m², house rental have an average size of 212 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 available 4,601 homes
💳 Possible discounts up to 67%
🌙 Nightly prices starting at $105
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 4,075 homes

Frequently Asked Questions

What is the average price per night for a vacation home in Wailea?

The price of a night's stay in Wailea starts at $105. If you would like to stay in a apartment rental, the average price is $654 per night. A house rental Wailea will cost $1,518 per night on average.

How many vacation homes are available for booking in Wailea?

There are 4,601 vacation rentals available for booking for your trip.

What amenities are most popular for vacation rentals in Wailea?

Travelers look for Pool, Air conditioning, and Kitchen when booking a vacation rental in Wailea.

How many vacation rentals with a pool are in Wailea?

Wailea has 4,075 Condo and Apartment rental options available for booking.

Are dogs allowed in vacation homes in Wailea?

Absolutely, currently there are 41 rentals in Wailea that allow dogs and the average cost is $2,343 per night.

What are the best months to travel to Wailea?

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

Vacation Destinations Near Wailea

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