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Condos in Wailea

Find 5,588 available offers from 25 partners
Wailea
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Wailea
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Popular Filters to find the Perfect Home Rental in Wailea

2 Adults
1 Bedroom
Pool
House
Pets allowed
4 Adults
Cabin

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 5,588 properties

Vacation rentals and apartments with air conditioning

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

Condo  Wailea
Jul 10 - Jul 17
-25%
$356
$268 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Wailea with Upper Pool

4.8
Outstanding (66 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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House  Wailea
Sep 25 - Oct 2
$549 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Wailea with Botanical Garden + Spectacular View

5.0
Outstanding (149 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Condo  Wailea
Oct 19 - Oct 26
-24%
$501
$379 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Family Friendly Beautiful Condo in Wailea with Pool & Grill + Ocean Views

4.4
Very good (16 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  Wailea
Aug 19 - Aug 26
-40%
$400
$238 per night
Condo ∙ 6 guests ∙ 2 bedrooms

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

5.0
Outstanding (62 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
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Condo  Wailea
Oct 19 - Oct 26
-42%
$397
$230 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Wailea with Pool & Patio + Incredible Views

4.8
Outstanding (27 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
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Condo  Wailea
Jul 27 - Aug 3
$250 per night
Condo ∙ 2 guests ∙ 1 bedroom

Charming Condo in Wailea with Private Parking + Next to Beach

4.9
Outstanding (90 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.

Cottage  Wailea
Jul 23 - Jul 30
-39%
$367
$226 per night
Cottage ∙ 5 guests ∙ 2 bedrooms

Cottage in Wailea with Grill, Yard & Patio + Aerial View

4.8
Outstanding (40 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
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Condo  Wailea
Sep 21 - Sep 28
-13%
$498
$435 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Wailea with Free Parking

4.9
Outstanding (27 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
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Condo  Wailea
Oct 19 - Oct 26
$376 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Wailea with Unassigned Parking + Ocean View

5.0
Outstanding (21 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Kitchen
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Best Vacation Home Deals in Wailea

Save up to 54%

House Wailea
Sep 6 - Sep 13
-35%
$1,699
$1,099 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Wailea with Beautiful Pool

5.0
Outstanding (37 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Aug 5 - Aug 12
-42%
$392
$227 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Beautiful Condo in Wailea with Upper Pool + Next to Beach

4.8
Outstanding (66 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Jul 26 - Aug 2
-54%
$839
$383 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Wailea with Pool, Patio & Grill + Mountain Views

4.9
Outstanding (60 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Book a welcoming vacation rental from $150 per night by searching through the 5,588 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 58%.

Recommended Vacation Rentals in Wailea

Find your perfect vacation rental in Wailea: from $150 per night

Villa Wailea
Aug 21 - Aug 28
$1,095 per night
Villa ∙ 10 guests ∙ 4 bedrooms

Villa in Wailea with Grill, Patio & Pool

5.0
Outstanding (33 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Villa Wailea
Aug 24 - Aug 31
$795 per night
Villa ∙ 10 guests ∙ 3 bedrooms

Nice Villa in Wailea with Private Balcony + Garden Views + Beach Nearby

4.8
Outstanding (60 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Sep 24 - Oct 1
$452 per night
Condo ∙ 9 guests ∙ 3 bedrooms

Condo in Kihei with Free Parking + Ocean Views

4.7
Excellent (95 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
May 10 - May 17
$379 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Beautiful Condo in Wailea with Patio, Grill & Pool + Next to Beach

4.8
Outstanding (77 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Sep 25 - Oct 2
-51%
$537
$266 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Wailea-Makena with Large Pool + Magnificent View

4.8
Outstanding (38 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Sep 24 - Oct 1
$380 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Wonderful Condo in Kihei with Pool, Patio & Grill + Amazing Views

4.9
Outstanding (166 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Sep 1 - Sep 8
-49%
$429
$220 per night
Condo ∙ 4 guests ∙ 2 bedrooms

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

4.9
Outstanding (95 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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House Wailea
Jul 23 - Jul 30
-33%
$1,785
$1,199 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Wailea with Beautiful Pool

4.9
Outstanding (99 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Oct 19 - Oct 26
$599 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo in Wailea with Botanical Garden + Ocean View

4.5
Excellent (14 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Budget-friendly Vacation Rentals in Wailea

Find Fantastic yet Inexpensive Offers

Condo Wailea
Sep 6 - Sep 13
$299 per night
Condo ∙ 5 guests ∙ 2 bedrooms

Condo in Wailea with Botanical Garden + 180-Degree Views

5.0
Outstanding (64 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Aug 24 - Aug 31
$586 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Charming Condo in Wailea-Makena with Patio, Grill & Pool + Oceanfront Views

4.6
Excellent (61 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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House Wailea
Sep 16 - Sep 23
$1,035 per night
House ∙ 10 guests ∙ 4 bedrooms

Private House in Wailea with Patio, Pool & Yard

5.0
Outstanding (93 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Top-Rated Rentals and Accommodations in Wailea

Book Vacation Rental Offers with the Highest User Rating

Condo Wailea
Aug 24 - Aug 31
-38%
$819
$505 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Spacious Condo in Wailea with Yard, Grill & Patio

5.0
Outstanding (53 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Villa Wailea
Sep 16 - Sep 23
-36%
$1,238
$795 per night
Villa ∙ 8 guests ∙ 3 bedrooms

Villa in Wailea with Grill, Sauna & Patio + Location View

5.0
Outstanding (42 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Jul 23 - Jul 30
-21%
$1,049
$829 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo in Kihei with Free Parking + Panoramic Views

4.9
Outstanding (37 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Popular Rental Amenities in Wailea

  • Pool (5,092)
  • Air conditioning (4,971)
  • Kitchen (5,138)
  • Parking (227)
  • Balcony/patio (2,147)
  • WiFi (5,451)
  • Washing machine (4,642)
  • TV (5,250)
  • Microwave (4,593)
  • Dishwasher (4,218)
  • Grill (3,841)
  • No smoking (5,179)

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 a rental with a pool or you need a vacation home with air conditioning, 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 December and reach an average of $966 a night (12/21 – 12/28), 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 May (5/25 – 6/1).

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 (4/19 – 4/26), as 88% of the rentals are booked. It will be easy to find a rental that suits you in a week of August (8/17 – 8/24), as 63% of the rentals are still available.

The Weather in Wailea

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7 days 7
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70°
10 days 10
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73°
10 days 10
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9 days 9
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13 days 13
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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

Sun, 26 May
82°
78°

10%

2 h

11 mi/h

Mon, 27 May
80°
78°

10%

0 h

7 mi/h

Tue, 28 May
80°
78°

10%

2 h

8 mi/h

Wed, 29 May
80°
78°

10%

0 h

10 mi/h

Thu, 30 May
78°
77°

10%

0 h

7 mi/h

Fri, 31 May
80°
78°

10%

1 h

5 mi/h

Sat, 1 Jun
80°
80°

10%

0 h

9 mi/h

Accommodations for your vacation in Wailea

3,249 of the 5,588 listed properties in Wailea are condo. They account for most of the accommodation types in this destination (85.1%). Interestingly, the average rental fee for this type of accommodation in particular is $626 a night, with an average size of 96 m². Furthermore, these rentals are perfect for 5 it represents the average number of vacationers condo can host in Wailea. Apartment rental are the other most common type of accommodation in Wailea. While condo in Wailea have an average size of 96 m², apartment rental have an average size of 82 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 5,588 rentals
💳 Possible discounts up to 58%
🌙 Nightly prices starting at $150
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 5,101 homes
8 reviews
Wailea vacation rentals have an average rating of 3.8/5 on 8 reviews left by travelers.

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 $150. If you would like to stay in a condo, the average price is $626 per night. A apartment rental Wailea will cost $641 per night on average.

How many vacation homes are available for booking in Wailea?

There are 5,588 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 5,101 Condo and Apartment rental options available for booking.

Are dogs allowed in vacation homes in Wailea?

Absolutely, currently there are 50 rentals in Wailea that allow dogs and the average cost is $2,010 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.

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