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

$459 avg / night
4.87 (15)
Wailea Ekolu Village 203
2 Bedroom | 2 Bath | Sleeps 4

Wailea Ekolu Village 203 - Wailea, HI

$309 avg / night
4.71 (24)
Wailea Grand Champions 147
2 Bedroom | 2 Bath | Sleeps 4

Wailea Grand Champions 147 - Wailea, HI

$269 avg / night
4.68 (38)
Wailea Grand Champions 149
2 Bedroom | 2 Bath | Sleeps 4

Wailea Grand Champions 149 - Wailea, HI

$373 avg / night
4.41 (17)
Wailea Grand Champions 87
2 Bedroom | 2 Bath | Sleeps 4

Wailea Grand Champions 87 - Wailea, HI

$484 avg / night
4.48 (29)

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Recent Wailea guest reviews

The unit was lovely with tasteful and simple decor. No tiki motif stuff. The amenities were wonderfully stocked so no need to rush out to Longs upon arrival. The staff at Grand Champion is always charming and helpful. However, we were very disappointed with the parking issue of Unit 149. The owner chooses to park his vehicle in his own unit 149 spot (the car has a tarpe over it) so we had to find a parking space that had guest sign indicated. Which turned out to be only 1 to every building. We had a party of four with 1 space so the use of space 149 should not have been a problem. I respect the owners to do whatever he wishes, but he should have indicated on the offer that there is no designated space for parking for the unit and the chance to park in the guest parking space is nil unless you plan to spend the evening in your condo every night for the fear of coming home late and having to park at the mall. Anyway, if you're a walker, Unit 149 is one of the best in the area (we have stayed at Grand Champion at least 5 times on Maui and never had parking issues). If you're like us, skip this unit and make sure that the other units have parking space that's available for you by calling Grand Champion first. Their customer service is incomparable. (maybe its Vacasa who was a little sloppy on this?) It's the little things in life that make us smile a little brighter, right?
lil n. | Nov 2024
Nice condo. Clean and tidy. Please provide paper towels in the kitchen and kleenex as well. It's a shame to have to go out to buy these things after we've already been to the store for what we need.
Clement C C. | Nov 2024
Convenient location
Kathy J. | Nov 2024
Wailea vacation rental FAQ

Yes. 237 of our Wailea vacation rentals have internet access, so you can stay connected throughout your trip.

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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.