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Wailea Vacation Rentals

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Wailea
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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Apartment
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Bed & Breakfast
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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Best Vacation Home Deals Wailea

Condo Wailea
Oct. 8 - Oct. 15
-45%
$919
$503 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
Details
Vrbo
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Condo Wailea
Sep. 9 - Sep. 16
-27%
$475
$346 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Kihei with Grill & Pool + Ocean View
4.3
"Very good" (93 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
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Condo Wailea
Aug. 20 - Aug. 27
-37%
$540
$340 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Kihei with Grill, Pool & Yard
4.8
"Excellent" (157 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
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Compare and find the perfect vacation rental from $234 per night by exploring the 3,701 properties available in Wailea. By comparing these vacation rentals, HomeToGo brings you the best deals and the highest rated accommodations in Wailea.

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Top-Rated Offers and Accommodations Wailea

Condo Wailea
Aug. 20 - Aug. 27
$520 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Wonderful Condo in Wailea-Makena with Pool, Grill & Yard + Ocean View + Next to Beach
4.9
"Excellent" (134 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
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Condo Wailea
Sep. 23 - Sep. 30
$352 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Wailea with Spacious Garden
4.9
"Excellent" (103 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
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Condo Wailea
Oct. 20 - Oct. 27
$441 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Wailea-Makena with Grill & Pool + Ocean Views
4.9
"Excellent" (84 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Recommended Vacation Rentals Wailea

Find your perfect vacation rental Wailea: from $226 per night

Condo Wailea
Aug. 26 - Sep. 2
$317 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
Details
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Condo Wailea
Sep. 16 - Sep. 23
$406 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
Details
Vrbo
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Condo Wailea
Oct. 14 - Oct. 21
$347 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
Details
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Condo Wailea
Sep. 16 - Sep. 23
$754 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Entire Condo in Wailea with Pool, Grill & Yard + Ocean View + Close to Beach
5.0
"Excellent" (115 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
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Condo Wailea
$234 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
Details
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Condo Wailea
$311 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
Details
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Condo Wailea
$359 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
$319 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Wailea with Pool & Grill + Mountain Views
4.9
"Excellent" (116 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
$326 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Wailea with Free Parking
4.9
"Excellent" (55 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Find Fantastic yet Inexpensive Rentals

Budget-friendly Rentals Wailea

Condo Wailea
Oct. 8 - Oct. 15
$348 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
Details
Vrbo
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Condo Wailea
Aug. 5 - Aug. 12
$450 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
Details
Vrbo
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Condo Wailea
Aug. 12 - Aug. 19
-37%
$622
$395 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
Details
Vrbo
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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
May 23 - May 30
-66%
$2,365
$804 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Wailea with Patio, Yard & Grill + Ocean View
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Details
Vacation Rental Pros
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Condo Air conditioning Wailea
Jul. 29 - Aug. 5
-25%
$786
$592 per night
Condo ∙ 4 guests ∙ 1 bedroom
Nice Condo in Wailea-Makena with Grill & Pool + Ocean View
4.9
"Excellent" (6 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Condo Air conditioning Wailea
Sep. 4 - Sep. 11
-65%
$2,187
$765 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Nice Condo in Wailea with Tropical Garden + Pleasant Views
Wailea, Wailea-Makena, Hawaii, United States
Free cancellation
Air conditioning
Details
RedAwning
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Apartments with a balcony or patio

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

Condo Balcony/Patio Wailea
Aug. 19 - Aug. 26
-21%
$1,118
$881 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Wailea with Jacuzzi, Pool & Yard
Wailea, Wailea-Makena, Hawaii, United States
Free cancellation
Balcony/Patio
Details
RedAwning
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Condo Balcony/Patio Wailea
Sep. 27 - Oct. 4
-39%
$1,437
$882 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Beautiful Condo in Wailea with Large Balcony + Golf View
Wailea, Wailea-Makena, Hawaii, United States
Free cancellation
Balcony/Patio
Details
Romvari Realty
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Condo Balcony/Patio Wailea
May 27 - Jun. 3
-33%
$1,224
$825 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Private Condo in Wailea with Free Parking + Ocean Views
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Details
RedAwning
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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
Sep. 23 - Sep. 30
-25%
$1,260
$950 per night
Condo ∙ 8 guests ∙ 1 bedroom
Beautiful Condo in Wailea with Grill, Hot Tub & Pool + Ocean Views
4.5
"Outstanding" (86 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
Details
HomeToGo
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Condo Internet Wailea
Sep. 23 - Sep. 30
-28%
$930
$668 per night
Condo ∙ 6 guests ∙ 1 bedroom
Condo in Wailea-Makena with Grill, Yard & Pool + Garden Views
4.2
"Very good" (82 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
Details
HomeToGo
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Condo Internet Wailea
May 27 - Jun. 3
-63%
$2,186
$808 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Wailea-Makena with Free Parking + Beautiful View
Wailea, Wailea-Makena, Hawaii, United States
Internet
Details
RedAwning
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Popular Rental Amenities Wailea

  • Internet (5,345)
  • TV (5,080)
  • Pool (5,062)
  • Kitchen (4,957)
  • Microwave (4,893)
  • Air conditioning (4,838)
  • No pets (4,835)
  • No smoking (4,680)
  • Dishwasher (4,408)
  • Washer (4,397)
  • Grill (3,888)
  • Yard (2,820)

Wailea is a wonderful vacation destination if you want a rental with a pool, as 92% of the properties there provide one. Condo with pools Wailea are a great option for groups of 5 and cost, on average, $1,283 per night. In Wailea, most of the properties with a pool are close to the water.

Price and Availability Index in Wailea

Vacation Rental Price Information Wailea

The graph shows average prices of rentals Wailea for the next twelve months. The most expensive prices are in December (12/23 - 12/30). Prices reach an average of $1,406 per night. However, in September (9/9 - 9/16), prices decrease to an average of $682 per night.

Rental Availability Information Wailea

The availability graph shows the percentage of available rentals Wailea. So far, the week with the least available rentals Wailea is in April (4/1 - 4/8). August (8/26 - 9/2) has got the highest percentage of available rentals.

The Weather Wailea

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Jan.
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Aug.
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Oct.
Nov.
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- Rainy days

Find the Wailea climate diagram. On average, the warmest month is August. Conversely, January is the coolest month Wailea, with temperatures going under 17° March is the wettest month.

7-Day Weather Forecast Wailea

Thu., 30 Mar.
25°
25°

10%

4 h

12 km/h

Fri., 31 Mar.
26°
24°

5%

3 h

13 km/h

Sat., 1 Apr.
25°
24°

15%

3 h

5 km/h

Sun., 2 Apr.
24°
22°

15%

0 h

10 km/h

Mon., 3 Apr.
24°
23°

15%

0 h

9 km/h

Tue., 4 Apr.
25°
23°

10%

2 h

8 km/h

Wed., 5 Apr.
25°
24°

10%

1 h

10 km/h

Where to find the best food 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 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 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 Wailea

🏡 Vacation rentals available 3,701 properties
💳 Discounts available up to 64%
🌙 Price per night from $234
⭐ Popular amenities Internet, Pool and TV
🏊 Vacation rentals with pools 5,481 properties

Frequently Asked Questions

What is the typical price of a vacation home Wailea?

Accommodation prices Wailea start at $234 per night.

What is the typical availability of House rental Wailea?

August has the highest availability of House rental Wailea, so you can expect plenty of selection, even for last-minute bookings.

What are the most popular vacation home amenities Wailea?

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

How many House rental and Villa can I find Wailea?

Wailea has 3,701 House rental and Villa available to book.

Are there pet-friendly vacation rentals Wailea?

Yes, there are 46 pet-friendly vacation rentals Wailea, with an average nightly price of $3,844.

What's the best month to visit Wailea?

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

We list offers from thousands of providers, including:

Booking.com Vacation Rentals Wailea TripAdvisor Vacation Rentals Wailea Vrbo Vacation Rentals Wailea Novasol Vacation Rentals Wailea Inter Chalet Vacation Rentals Wailea Interhome Vacation Rentals Wailea HouseTrip Vacation Rentals Wailea Belvilla Vacation Rentals Wailea Homestay.com Vacation Rentals Wailea Ski Planet Vacation Rentals Wailea Only-apartments Vacation Rentals Wailea James Villa Holidays Vacation Rentals Wailea

Vacation Destinations Near Wailea

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