Wailea Condo Rentals

Compare 5 vacation rentals.
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Make Wailea your next getaway

Relax into a slice of paradise with a Wailea vacation rental. With stunning beaches, top-rated resorts, and world-class golf courses, you’ll have everything you need for an amazing getaway at your fingertips. Choose from amenities like ocean views, direct beach access, and outdoor pools to find the right home base for your adventure.

Top Wailea property types

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Condo rentals

View 5 Condo rentals

Popular amenities for Wailea vacation rentals

Popular
Hot tub Internet Pool
Wailea Grand Champions 149
2 Bedroom | 2 Bath | Sleeps 4

Wailea Grand Champions 149 - Wailea, HI

$272 avg / night
(excludes fees and taxes)
4.45 (20)
Wailea Grand Champions 7
2 Bedroom | 2 Bath | Sleeps 6

Wailea Grand Champions 7 - Wailea, HI

$274 avg / night
(excludes fees and taxes)
5.0 (1)
Wailea Ekolu Village 410
2 Bedroom | 2.5 Bath | Sleeps 4

Wailea Ekolu Village 410 - Wailea, HI

$371 avg / night
(excludes fees and taxes)
4.9 (21)
Wailea Ekolu Village 203
2 Bedroom | 2 Bath | Sleeps 4

Wailea Ekolu Village 203 - Wailea, HI

$290 avg / night
(excludes fees and taxes)
4.71 (28)
Wailea Grand Champions 87
2 Bedroom | 2 Bath | Sleeps 4

Wailea Grand Champions 87 - Wailea, HI

$441 avg / night
(excludes fees and taxes)
4.56 (34)

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Recent Wailea guest reviews

Could not be better location for price. 2 min walk to coffee shop. Ocean views from patio. Very comfortable, clean and well decorated condo. 5 min walk to shops. Could not be better for something not directly on water. Vacasa was excellent for communication. Our only reason for not 5 stars was it had very week wifi, it I am sure they are getting it fixed. Everything else was 5+ stars. Will definitely stay in this area again. We have stayed at many places and this is the best for location.
ryan m. | Nov 2025
Property is as nice as described and shown in pictures (except you also get access to an excellent outdoor grill that the listing didn't mention, at least when we booked). GREAT A/C, good supply of useful beach equipment (chairs, umbrellas, etc.). Impressively clean for the tropical environment (or anywhere).
Jason K. | Nov 2025
Easy walk to the Shops and beaches.
David S. | Sep 2025
Wailea vacation rental FAQ

Yes. 209 of our Wailea vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Wailea vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Wailea team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Wailea, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Explore our Wailea, HI, vacation rentals

Wailea vacation rentals are located on the southwest coast of Maui, offering travelers a luxurious and serene escape. From here, you can enjoy three world-class golf courses, incredible beaches and snorkeling sites, and nearby parks. Find the perfect home away from home with amenities like ocean views, direct beach access, outdoor pools, hot tubs, private balconies, and more. 

Beach hop to your heart’s content between Wailea Beach, Big Beach, or Makena Cove, and prepare to be awed by their picturesque beauty. Experience fantastic snorkeling at Molokini Crater, tee off at championship golf courses, and indulge in upscale dining along the Wailea Beach Walk. For more outdoor adventure, lace up your sneakers for scenic hikes and waterfalls in nearby Haleakalā National Park.