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Wailea Vacation Rentals

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Wailea
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Up to $100
$100 - $199
From $200
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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 29%

Condo Wailea
Dec 16 - Dec 23
-22%
$461
$359 per night
Condo ∙ 2 guests ∙ 1 bedroom

Nice Condo in Wailea with Free Parking + Next to Beach

5.0
Outstanding (40 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Apartment Wailea
Dec 9 - Dec 16
-29%
$598
$423 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Rental Apartment in Wailea with Patio & Pool

4.5
Excellent (4 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
FlipKey
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Condo Wailea
Apr 5 - Apr 12
-20%
$515
$411 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo in Wailea-Makena with Grill, Yard & Pool

4.8
Outstanding (28 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Compare and find the perfect vacation rental from $359 per night by exploring the 4,778 properties available in Wailea. By comparing these vacation rentals, HomeToGo brings you the best deals and the highest rated accommodations in Wailea.

Top-Rated Offers and Accommodations in Wailea

Book Vacation Rentals with the Highest User Rating

Condo Wailea
Aug 31 - Sept 7
$504 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Wailea with Grill, Yard & Pool

4.8
Outstanding (230 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Aug 31 - Sept 7
$378 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Wailea with Pool, Grill & Yard + Beach Nearby

4.8
Outstanding (146 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Apr 13 - Apr 20
$928 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Kihei with Free Parking + Ocean Views

4.6
Excellent (20 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Recommended Vacation Rentals in Wailea

Find your perfect vacation rental in Wailea: from $227 per night

Condo Wailea
May 25 - Jun 1
$463 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo in Wailea with Pool, Grill & Yard

5.0
Outstanding (1 rating)
Wailea, Wailea-Makena, Hawaii, United States
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House Wailea
Jun 1 - Jun 8
$2,216 per night
House ∙ 10 guests ∙ 4 bedrooms

Private Vacation Home in Wailea with Yard & Pool

4.8
Outstanding (25 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Details
FlipKey
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Condo Wailea
Apr 4 - Apr 11
$428 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo in Wailea with Open Parking

4.0
Very good (24 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Apr 4 - Apr 11
$369 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo in Wailea with Large Pool

4.5
Excellent (107 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
May 25 - Jun 1
$708 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Entire Condo in Wailea with Complimentary Parking + Ocean View

5.0
Outstanding (89 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Dec 16 - Dec 23
$398 per night
Condo ∙ 4 guests ∙ 1 bedroom

Wonderful Condo in Wailea-Makena with Yard, Grill & Pool + Ocean View + Next to Beach

4.7
Excellent (38 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Apr 4 - Apr 11
-26%
$627
$462 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Wonderful Condo in Wailea with Quiet Patio + Mountain Views + Next to Beach

4.5
Excellent (50 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Jun 1 - Jun 8
$679 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo in Wailea with Botanical Garden + Volcano View

5.0
Outstanding (127 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Dec 9 - Dec 16
$633 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Family Friendly Condo in Wailea with Botanical Garden + Ocean Views

3.5
Good (65 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Budget-friendly Rentals in Wailea

Find Fantastic yet Inexpensive Rentals

House Wailea
Dec 9 - Dec 16
$767 per night
House ∙ 4 guests ∙ 2 bedrooms

Lovely Vacation Home in Wailea with Yard, Pool & Grill + Ocean View + Beach Nearby

4.5
Excellent (62 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Apr 13 - Apr 20
$711 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Wailea with Free Parking + Spectacular Views

4.0
Very good (14 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Apr 13 - Apr 20
$427 per night
Condo ∙ 4 guests ∙ 1 bedroom

Lovely Condo in Wailea-Makena with Pool & Grill + Next to Beach

4.9
Outstanding (100 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
Dec 16 - Dec 23
$527 per night
Condo ∙ 4 guests ∙ 1 bedroom

Entire Condo in Wailea-Makena with Yard, Pool & Grill

4.8
Outstanding (80 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Condo Wailea
Apr 13 - Apr 20
$624 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Wailea with Updated Pool + Ocean Views

4.8
Outstanding (107 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Condo Wailea
Apr 4 - Apr 11
$428 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo in Wailea with Pool & Grill + Ocean Views + Next to Beach

3.3
(32 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Apartments with a balcony or patio

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

Condo Wailea
Apr 13 - Apr 20
$657 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Wailea with Botanical Garden

5.0
Outstanding (105 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Details
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Condo Wailea
Apr 13 - Apr 20
-17%
$469
$390 per night
Condo ∙ 4 guests ∙ 1 bedroom

Wonderful Condo in Wailea-Makena with Botanical Garden + Ocean View + Beach Nearby

4.4
Very good (51 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
Details
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Condo Wailea
Dec 16 - Dec 23
$391 per night
Condo ∙ 4 guests ∙ 1 bedroom

Great Condo in Wailea with Large Pool + Ocean View

4.9
Outstanding (190 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
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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
May 25 - Jun 1
$398 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
Kitchen
Details
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Condo Wailea
Dec 16 - Dec 23
-39%
$868
$526 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Wailea with Pool, Grill & Jacuzzi + Enjoy Views

4.9
Outstanding (63 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
Details
Vrbo
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Condo Wailea
Apr 4 - Apr 11
$445 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo in Wailea with Jacuzzi, Pool & Grill + Spectacular Views

4.8
Outstanding (28 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
Details
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Popular Rental Amenities in Wailea

  • Pool (4,504)
  • WiFi (4,812)
  • Air conditioning (4,375)
  • Balcony/patio (582)
  • Kitchen (4,481)
  • Parking (229)
  • Washing machine (4,170)
  • TV (4,557)
  • Dishwasher (3,855)
  • Grill (3,475)
  • Microwave (4,213)
  • Jacuzzi (665)

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 in Wailea are a great option for groups of 5 and cost, on average, $1,192 per night. In Wailea, many of the properties with a pool are close to the 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 average prices of rentals in Wailea for the next twelve months. The most expensive prices are in February (2/10 – 2/17). Prices reach an average of $1,128 per night. However, in September (9/21 – 9/28), prices decrease to an average of $689 per night.

Rental availability information in Wailea

The availability graph shows the percentage of available rentals in Wailea. So far, the week with the least available rentals in Wailea is in December (12/23 – 12/30). August (8/31 – 9/7) has got the highest percentage of available rentals.

The Weather in Wailea

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17°
7 days 7
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12 days 12
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13 days 13
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11 days 11
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11 days 11
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10 days 10
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13 days 13
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

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

7-Day Weather Forecast in Wailea

Wed., 6 Dec.
28°
26°

10%

5 h

15 km/h

Thu., 7 Dec.
26°
26°

15%

2 h

7 km/h

Fri., 8 Dec.
25°
24°

10%

5 h

15 km/h

Sat., 9 Dec.
25°
24°

10%

5 h

11 km/h

Sun., 10 Dec.
26°
25°

10%

4 h

9 km/h

Mon., 11 Dec.
25°
25°

10%

2 h

9 km/h

Tue., 12 Dec.
27°
26°

10%

6 h

24 km/h

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 4,778 homes
💳 Possible discounts up to 34%
🌙 Nightly prices starting at $359
⭐ Popular amenities Pool, Internet and Air conditioning
🏊 Vacation rentals with pools 4,409 homes

Frequently Asked Questions

What is the typical price of a vacation home in Wailea?

Accommodation prices in Wailea start at $359 per night.

What is the typical availability of House rental in Wailea?

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

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.

How many House rental and Apartment rental can I find in Wailea?

Wailea has 4,778 House rental and Apartment rental available to book.

Are there pet-friendly vacation rentals in Wailea?

Yes, there are 46 pet-friendly vacation rentals in Wailea, with an average nightly price of $2,885.

What's the best month to visit Wailea?

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

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