Wailea Vacation Rentals - HomeToGo base64Hash Wailea Vacation Rentals - HomeToGo

Wailea Vacation Rentals

Find 7,576 available home rentals from 30 partners
Anytime
1 guest
Anytime
1 guest

Top 15 Recommended vacation rentals in Wailea

Find your perfect vacation rental in Wailea from just $267 per night!

House Wailea
May 26 - Jun 2
House ∙ 6 guests ∙ 2 bedrooms

93 m² House

Wailea, Wailea-Makena, Hawaii, United States
$1,148
per night
Outstanding(111 ratings)
$1,148
per night
View deal
Villa Wailea
-29%
Nov 15 - Nov 22
Villa ∙ 4 guests ∙ 1 bedroom

60 m² Villa

Wailea, Wailea-Makena, Hawaii, United States
$1,098$785
per night
Outstanding(145 ratings)
$1,098$785
per night
View deal
House Wailea
-7%
Jul 16 - Jul 23
House ∙ 6 guests ∙ 3 bedrooms

214 m² House

Wailea, Wailea-Makena, Hawaii, United States
$1,440$1,334
per night
Outstanding(158 ratings)
$1,440$1,334
per night
View deal
Condo Wailea
Nov 15 - Nov 22
Condo ∙ 8 guests ∙ 4 bedrooms

130 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$1,143
per night
Outstanding(98 ratings)
$1,143
per night
View deal
House Wailea
Jan 27 - Feb 3
House ∙ 6 guests ∙ 3 bedrooms

93 m² House

Wailea, Wailea-Makena, Hawaii, United States
$978
per night
Excellent(63 ratings)
$978
per night
View deal
House Wailea
-3%
May 26 - Jun 2
House ∙ 7 guests ∙ 3 bedrooms

House

Wailea, Wailea-Makena, Hawaii, United States
$1,243$1,200
per night
Outstanding(92 ratings)
$1,243$1,200
per night
View deal
Condo Wailea
May 26 - Jun 2
Condo ∙ 8 guests ∙ 4 bedrooms

112 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$1,013
per night
Outstanding(63 ratings)
$1,013
per night
View deal
Condo Wailea
Aug 15 - Aug 22
Condo ∙ 4 guests ∙ 2 bedrooms

47 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$513
per night
Outstanding(63 ratings)
$513
per night
View deal
Condo Wailea
Jul 16 - Jul 23
Condo ∙ 5 guests ∙ 5 bedrooms

82 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$603
per night
Outstanding(150 ratings)
$603
per night
View deal
Condo Wailea
Aug 15 - Aug 22
Condo ∙ 5 guests ∙ 5 bedrooms

82 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$599
per night
Outstanding(141 ratings)
$599
per night
View deal
House Wailea
May 26 - Jun 2
House ∙ 6 guests ∙ 3 bedrooms

1175 m² House

Wailea, Wailea-Makena, Hawaii, United States
$445
per night
Excellent(68 ratings)
$445
per night
View deal
Condo Wailea
Aug 15 - Aug 22
Condo ∙ 4 guests ∙ 2 bedrooms

71 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$759
per night
Excellent(99 ratings)
$759
per night
View deal
Condo Wailea
-39%
May 16 - May 23
Condo ∙ 4 guests ∙ 2 bedrooms

100 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$778$478
per night
$778$478
per night
View deal
Condo Wailea
Jul 16 - Jul 23
Condo ∙ 4 guests ∙ 2 bedrooms

76 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$405
per night
Outstanding(207 ratings)
$405
per night
View deal
Condo Wailea
May 26 - Jun 2
Condo ∙ 6 guests ∙ 3 bedrooms

114 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
$510
per night
Outstanding(82 ratings)
$510
per night
View deal

Cabins with a sauna

Condo  Wailea
Sept 29 - Oct 6
-28%
$916
$457 per night
Condo ∙ 2 guests ∙ 1 bedroom

65 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
Sauna
View deal
Apartment  Wailea
Sept 28 - Oct 5
-31%
$1,034
$419 per night
Apartment ∙ 4 guests ∙ 1 bedroom

66 m² Apartment

Wailea, Wailea-Makena, Hawaii, United States
Free cancellation
Sauna
View deal
Condo  Wailea
May 31 - Jun 7
-28%
$1,039
$566 per night
Condo ∙ 6 guests ∙ 2 bedrooms

88 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
Sauna
View deal
See all offers

Apartments with a balcony or patio

Condo  Wailea
Sept 28 - Oct 5
-30%
$583
$385 per night
Condo ∙ 4 guests ∙ 1 bedroom

76 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
Nov 30 - Dec 7
-38%
$724
$397 per night
Condo ∙ 4 guests ∙ 1 bedroom

79 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Resort  Wailea
Jul 19 - Jul 26
$266 per night
4 guests ∙ 1 bedroom

Resort

3.5
Good(2 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
See all offers

Vacation rentals with a fireplace

Villa  Wailea
Apr 30 - May 7
-64%
$5,836
$2,192 per night
Villa ∙ 8 guests ∙ 3 bedrooms

203 m² Villa

Wailea, Wailea-Makena, Hawaii, United States
Fireplace
View deal
Villa  Wailea
Apr 26 - May 3
-57%
$11,414
$5,266 per night
Villa ∙ 8 guests ∙ 3 bedrooms

271 m² Villa

Wailea, Wailea-Makena, Hawaii, United States
Fireplace
View deal
Condo  Wailea
Nov 30 - Dec 7
-47%
$1,135
$917 per night
Condo ∙ 7 guests ∙ 2 bedrooms

138 m² Condo

Wailea, Wailea-Makena, Hawaii, United States
Fireplace
View deal
See all offers

Best Vacation Home Deals in Wailea

Save up to 7%

House Wailea
Nov 15 - Nov 22
-7%
$1,275
$1,176 per night
House ∙ 6 guests ∙ 3 bedrooms

143 m² House

5.0
Outstanding(109 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Nov 15 - Nov 22
-7%
$702
$647 per night
Condo ∙ 6 guests ∙ 3 bedrooms

106 m² Condo

4.7
Excellent(179 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Jan 27 - Feb 3
-4%
$1,354
$1,304 per night
Condo ∙ 8 guests ∙ 4 bedrooms

135 m² Condo

4.9
Outstanding(35 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Discover a vacation rental meeting your needs among the 7,576 great properties from 29 providers in Wailea. HomeToGo instantaneously compares all of these vacation homes so you can save up to 36%!

Budget-friendly Rentals in Wailea

Find Fantastic yet Inexpensive Rentals

Condo Wailea
May 26 - Jun 2
$807 per night
Condo ∙ 6 guests ∙ 3 bedrooms

76 m² Condo

5.0
Outstanding(21 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Jul 16 - Jul 23
$684 per night
Condo ∙ 4 guests ∙ 2 bedrooms

93 m² Condo

4.9
Outstanding(102 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $1,119 per night
Condo ∙ 8 guests ∙ 4 bedrooms

129 m² Condo

5.0
Outstanding(64 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Top-Rated Offers and Accommodations in Wailea

Book Vacation Rentals with the Highest User Rating

Condo Wailea
Jul 16 - Jul 23
-7%
$771
$703 per night
Condo ∙ 5 guests ∙ 3 bedrooms

121 m² Condo

5.0
Outstanding(220 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
May 26 - Jun 2
$546 per night
Condo ∙ 4 guests ∙ 2 bedrooms

59 m² Condo

4.9
Outstanding(97 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
May 26 - Jun 2
$438 per night
4 guests ∙ 2 bedrooms

House

4.7
Excellent(55 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Customer ratings and reviews

How are reviews collected?
Robert M.
Guest verified by HomeToGo

Great place, everything you need and want for you stay. Living area and Master bedroom views great.

Reviewed on 9/25/2024 | Group
Condo Wailea
from $1,434 per night
HomeToGo
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(49 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Kerry H.
Guest verified by HomeToGo

We loved this condo for our family of four (2 teenage boys). It had enough space for us to spread out. The location is perfect! Easy access to the beach, town and the most amazing spot to watch the sunset! Someone in the reviews mentioned road noise, I live in a rural quiet place and was a bit worried, but it was not an issue at all!

Reviewed on 10/30/2023 | Family
Condo Wailea
from $612 per night
HomeToGo
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
David M.
Guest verified by HomeToGo

A great clean affordable option for a week away. Many options within walking distance and everything you need to enjoy your stay is supplied.

Reviewed on 10/27/2023 | Couple
Condo Wailea
from $335 per night
HomeToGo
Condo ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(95 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Wailea

  • Pool (6,160)
  • WiFi (7,363)
  • Air conditioning (6,669)
  • Balcony/patio (2,146)
  • Kitchen (6,683)
  • Parking (311)
  • Washing machine (5,353)
  • TV (6,738)
  • Dishwasher (4,325)
  • Grill (4,199)
  • Microwave (5,621)
  • Jacuzzi (2,630)

Finding a vacation rental with a pool shouldn't be too difficult in Wailea. Most of the properties offer one. Condo with pools in Wailea are a good choice for groups of 5 and usually cost around $1,120 a night. Among these rentals, 40 of them are situated within 2 kilometres of 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 the average rental prices for the next twelve months in Wailea. The most expensive prices are in February (2/7 – 2/14). Prices reach an average of $1,179 per night. Wailea is cheaper in a week of September (9/27 – 10/4), where prices are on average $690 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 January (1/24 – 1/31), where 84% of the vacation rentals are booked. Conversely, it is in May (5/17 – 5/24) 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.

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 7,576 rentals
💳 Possible discounts up to 36%
🌙 Nightly prices starting at $267
⭐ Popular amenities Pool, Internet and Air conditioning
🏊 Vacation rentals with pools 6,147 homes
320,593 reviews
Wailea vacation rentals have an average rating of 4.6/5 on 320,593 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Wailea?

We found 7,576 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 250 pet-friendly vacation rentals in Wailea, with an average nightly price of $2,491.

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.

Top cities to visit

Discover more vacation accommodations

Top Vacation Destinations

Show more
image-tag