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Wailea Vacation Rentals

Find 5,470 available offers from 25 partners
Wailea
Anytime
Guests
Wailea
Anytime
Guests

Popular Filters to find the Perfect Rental in Wailea

2 Adults
1 Bedroom
4 Adults
Pets allowed
Pool
House
Internet

Vacation rentals and apartments with air conditioning

Condo  Wailea
Oct 26 - Nov 2
-21%
$889
$703 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with Pool

4.8
Outstanding (9 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Free cancellation
Air conditioning
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Condo  Wailea
Aug 14 - Aug 21
$810 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Family-Oriented Condo with Garden, Pool & BBQ | Good for Workation

4.8
Outstanding (20 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Condo  Wailea
Jan 11 - Jan 18
$1,122 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with Pool

5.0
Outstanding (5 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
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Vacation rentals with Wi-Fi

House  Wailea
Aug 14 - Aug 21
$1,002 per night
House ∙ 6 guests ∙ 3 bedrooms

Child-Friendly Ample House with Patio, Yard & Barbecue | Nature View

5.0
Outstanding (113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
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Condo  Wailea
Jan 11 - Jan 18
$1,151 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Family-Friendly Nice Condo with Patio, Pool & Yard | Beach Nearby

5.0
Outstanding (84 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
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Condo  Wailea
Aug 14 - Aug 21
$227 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with Patio, Garden & Grill

4.5
Excellent (108 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Internet
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Apartments with a balcony or patio

Condo  Wailea
Feb 15 - Feb 22
$899 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with Patio & Pool | Nature View

4.8
Outstanding (25 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
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Condo  Wailea
Aug 14 - Aug 21
$493 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Family-Friendly Condo with Patio, Pool & Grill

5.0
Outstanding (109 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
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Apartment  Wailea
Aug 14 - Aug 21
$318 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment with Patio, Garden & Barbeque | Mountain View

4.8
Outstanding (154 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
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Best Vacation Home Deals in Wailea

Save up to 62%

Condo Wailea
Aug 11 - Aug 18
-62%
$650
$244 per night
Condo ∙ 2 guests ∙ 1 bedroom

Condo with Garden, Barbeque & Pool

4.2
Very good (59 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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House Wailea
Aug 14 - Aug 21
-30%
$1,035
$721 per night
House ∙ 7 guests ∙ 2 bedrooms

House with Patio, Heated Pool & BBQ

3.4
(60 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Aug 14 - Aug 21
-28%
$564
$407 per night
Condo ∙ 4 guests ∙ 1 bedroom

Fully Equipped Condo with Pool, Grill & Jacuzzi | Mountain View | Beach Nearby

4.7
Excellent (32 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Discover a vacation rental meeting your needs among the 5,470 great properties from 26 providers in Wailea. HomeToGo instantaneously compares all of these vacation homes so you can save up to 62%!

Recommended Vacation Rentals in Wailea

Find your perfect vacation rental in Wailea: from $255 per night

House Wailea
Jan 11 - Jan 18
$2,217 per night
House ∙ 8 guests ∙ 3 bedrooms

House with Sauna, Pool & Barbeque

5.0
Outstanding (92 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Aug 14 - Aug 21
$555 per night
Condo ∙ 8 guests ∙ 2 bedrooms

Fully Equipped Wonderful Condo with Grill, Pool & Garden | Nature View | Next to the Beach

4.8
Outstanding (59 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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House Wailea
Jan 11 - Jan 18
$1,039 per night
House ∙ 7 guests ∙ 3 bedrooms

Vacation Home with Yard, Terrace & Barbecue | Nature View

4.7
Excellent (97 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Aug 14 - Aug 21
$1,100 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Child-Friendly Condo with Garden, Heated Pool & BBQ | Next to the Beach

4.5
Excellent (83 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Aug 14 - Aug 21
$454 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Fully Equipped Condo with Grill & Pool | City View | Next to the Beach

4.8
Outstanding (27 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Jan 11 - Jan 18
$1,193 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Fully Equipped Pleasant Condo with Pool | Beach Nearby

5.0
Outstanding (14 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Aug 14 - Aug 21
$330 per night
Condo ∙ 2 guests ∙ 1 bedroom

Condo with BBQ, Pool & Patio | City View | Close to the Beach

5.0
Outstanding (81 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Jan 11 - Jan 18
$591 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with BBQ & Pool | Nature View | Suitable for Remote Work

3.5
Good (2 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Villa Wailea
Aug 14 - Aug 21
$1,789 per night
Villa ∙ 7 guests ∙ 3 bedrooms

Fully Equipped Beautiful Villa with Barbeque & Heated Pool | Beach Nearby

5.0
Outstanding (89 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Budget-friendly Rentals in Wailea

Find Fantastic yet Inexpensive Rentals

Condo Wailea
Aug 14 - Aug 21
$507 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Fully Equipped Charming Condo with Barbecue, Heated Pool & Yard

4.8
Outstanding (28 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Aug 14 - Aug 21
$499 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with BBQ, Yard & Patio

4.5
Excellent (21 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Jan 11 - Jan 18
$991 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with Patio, Yard & Pool

4.9
Outstanding (148 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Top-Rated Offers and Accommodations in Wailea

Book Vacation Rentals with the Highest User Rating

Condo Wailea
Aug 14 - Aug 21
$645 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Fully Equipped Condo with Garden, Terrace & Pool | Nature View | Next to the Beach

5.0
Outstanding (106 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Jan 11 - Jan 18
$2,084 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Fully Equipped Charming Condo with BBQ, Pool & Patio | Next to the Beach

4.6
Excellent (61 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Condo Wailea
Jan 11 - Jan 18
$900 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Fully Equipped Condo with Pool, Grill & Garden | City View | Beach Nearby

4.6
Excellent (20 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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Popular Rental Amenities in Wailea

  • Pool (5,063)
  • WiFi (5,415)
  • Air conditioning (4,920)
  • Balcony/patio (2,051)
  • Kitchen (5,058)
  • Parking (231)
  • Washing machine (4,607)
  • TV (5,157)
  • Dishwasher (4,132)
  • Grill (3,797)
  • Microwave (4,477)
  • Jacuzzi (909)

Finding a vacation rental with a pool shouldn't be too difficult in Wailea. Nearly all of the properties offer one. Condo with pools in Wailea are a good choice for groups of 5 and usually cost around $1,113 a night. Among these rentals, 54 of them are situated within 2 kilometres of water.

Price and Availability Index in Wailea

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Vacation Rental Price Information in Wailea

The graph shows the average rental prices for the next twelve months in Wailea. The most expensive prices are in December (12/21 – 12/28). Prices reach an average of $1,154 per night. Wailea is cheaper in a week of July (7/6 – 7/13), where prices are on average $625 a night.

Rental availability information in Wailea

The availability graph shows the percentage of available vacation rentals in Wailea. The week with the highest booking rate in the next 12 months is in April (4/26 – 5/3), where 89% of the vacation rentals are booked. Conversely, it is in August (8/31 – 9/7) that the highest percentage of vacation homes are available.

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.

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 5,470 rentals
💳 Possible discounts up to 62%
🌙 Nightly prices starting at $255
⭐ Popular amenities Pool, Internet and Air conditioning
🏊 Vacation rentals with pools 5,001 homes
3 reviews
Wailea vacation rentals have an average rating of 4/5 on 3 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Wailea?

We found 5,470 vacation homes in Wailea available for your next trip.

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.

Are there pet-friendly vacation rentals in Wailea?

Yes, there are 80 pet-friendly vacation rentals in Wailea, with an average nightly price of $2,732.

What's the best month to visit Wailea?

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

Find the perfect Wailea home to match your style

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