Wailea Condo Rentals

Compare 5 vacation rentals.
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

Popular amenities for Wailea vacation rentals

Popular
Dog-friendly Hot tub Internet
Wailea Ekolu Village 410
2 Bedroom | 2.5 Bath | Sleeps 4

Wailea Ekolu Village 410 - Wailea, HI

$476 avg / night
4.87 (15)
Wailea Ekolu Village 203
2 Bedroom | 2 Bath | Sleeps 4

Wailea Ekolu Village 203 - Wailea, HI

$325 avg / night
4.74 (23)
Wailea Grand Champions 147
2 Bedroom | 2 Bath | Sleeps 4

Wailea Grand Champions 147 - Wailea, HI

$282 avg / night
4.68 (38)
Wailea Grand Champions 149
2 Bedroom | 2 Bath | Sleeps 4

Wailea Grand Champions 149 - Wailea, HI

$393 avg / night
4.44 (16)
Wailea Grand Champions 87
2 Bedroom | 2 Bath | Sleeps 4

Wailea Grand Champions 87 - Wailea, HI

$502 avg / night
4.48 (29)

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Recent Wailea guest reviews

Convenient location
Kathy J. | Nov 2024
All the wonderful amenities of home in paradise.
Catherine J C. | Oct 2024
I loved the location of this unit within the complex. Easy walking distance to the Shops @ Wailea and the beach front walk.
Debra T. | Sep 2024
Wailea vacation rental FAQ

Yes. 240 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.

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.