Wailea Condo Rentals

Compare 5 vacation rentals.
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USA > Hawaii > Wailea

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.

Explore Wailea condo rentals, and more

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Condo rentals

View 5 Condo rentals

Wailea vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Wailea Grand Champions 149
2 Bed | 2 Bath | Sleeps 4

Wailea Grand Champions 149 - Wailea, HI

$515 avg / night
4.41 (17)
Wailea Ekolu Village 203
2 Bed | 2 Bath | Sleeps 4

Wailea Ekolu Village 203 - Wailea, HI

$458 avg / night
4.72 (25)
Wailea Grand Champions 87
2 Bed | 2 Bath | Sleeps 4

Wailea Grand Champions 87 - Wailea, HI

$695 avg / night
4.48 (29)
Wailea Grand Champions 147
2 Bed | 2 Bath | Sleeps 4

Wailea Grand Champions 147 - Wailea, HI

$404 avg / night
4.68 (38)
Wailea Ekolu Village 410
2 Bed | 2.5 Bath | Sleeps 4

Wailea Ekolu Village 410 - Wailea, HI

$637 avg / night
4.88 (17)

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Recent Wailea vacation rental reviews

The home was beautiful and located close to shops and the shore.
Nancy H. | Jan 2025
Exceeded expectations! Just like the pics and then some. Wonderful stay, would return and would recommend. Mahalo!
Connor J. | Dec 2024
The condo is very comfortable and beautifully furnished with nice little decorative touches everywhere. Appliances were like new, everything very clean, and the remote controlled window shades are a great idea. The location is excellent, with a fabulous view of the ocean and surrounded area. Very short drive to shopping and restaurants and a wonderful beach. There is a very nice pool for the complex, and the landscaping is lovely. We would certainly consider booking this unit again.
Carole L. | Dec 2024
Wailea Frequently Asked Questions

Yes. 232 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 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 worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Wailea, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional 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.