South Maui Vacation Rentals

Compare 147 vacation rentals.
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USA > Hawaii > South Maui

Make South Maui your next getaway

The Aloha Spirit is alive and well in South Maui, a picture-perfect paradise of golden sand beaches, wide-stretching coastline, and lush, tropical headlands. From the otherworldly landscape of Haleakala’s red sand crater to the sloping shores of Makena Beach, South Maui’s majesty is a must-see—and you’ll be front and center to the area’s abundant beauty when you book one of our South Maui vacation rentals.

Explore South Maui condo rentals, studios, cottages, and more

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Condo rentals

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Studios

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Cottages

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Popular amenities for South Maui vacation rentals

Popular
Dog-friendly Hot tub Internet
Island Surf 601B
1 Bedroom | 1 Bath | Sleeps 4

Island Surf 601B - Kihei, HI

$255 avg / night
4.68 (22)
Hale Li'ili'i at Keawakapu #201
0 Bedroom | 1 Bath | Sleeps 2

Hale Li'ili'i at Keawakapu #201 - Kihei, HI

$166 avg / night
4.89 (18)
Kihei Kai Nani 211
1 Bedroom | 1 Bath | Sleeps 4

Kihei Kai Nani 211 - Kihei, HI

$220 avg / night
4.62 (16)
Kihei Akahi C316
1 Bedroom | 1 Bath | Sleeps 4

Kihei Akahi C316 - Kihei, HI

$178 avg / night
4.04 (28)
Wailea Grand Champions 149
2 Bedroom | 2 Bath | Sleeps 4

Wailea Grand Champions 149 - Wailea, HI

$302 avg / night
4.44 (18)

View 142 more homes

Browse more vacation rental amenities in South Maui

Pool | Electric vehicle charger | Ocean view | Oceanfront | Water view | Waterfront | A/C | Elevator | Washer/dryer | Balcony

Recent South Maui guest reviews

We stayed here for 9 days on our honeymoon and really loved it. The unit was spacious, updated renovations, the appliances and AC worked perfectly well and we enjoyed heading to the pool in the afternoons. Great location too, 5 minute walk to the beach for the sunsets and a 3 minute drive to Keawakapu beach where we spent basically every morning. The only negative thing I could say is the wifi would cut out randomly for several minutes at a time but this was so minor and we would definitely come stay here again.
Clayton G. | Apr 2025
Location is great and this unit was very well equipped and extremely comfortable!!!
Heidi H. | Apr 2025
It was an absolute dream of a stay! It truly felt like a home away from home! thank you!!
Tom M. | Apr 2025
South Maui vacation rental FAQ

Yes. 147 of our South Maui 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 South Maui 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 South Maui 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 South Maui, 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


Where is South Maui?

Bound by the popular tourist haven of Kihei on the northwest side, South Maui extends over 50 miles southeast to the pasturelands of Kaupo at the base of Haleakala National Park. The area is accessed via Highway 37, which cuts through the middle of the island then turns into Piilani Highway in the south.

Things to Do in South Maui

Whether you're coming to the island to sunbathe, shop, or wind around stunning volcanic coastline on a scenic drive, you’ll find it all just minutes from our South Maui vacation rentals.

Start your trip with a bike tour of the oceanfront promenade in Kihei, then head about nine miles south to pick up a Hawaiian souvenir at the open-air Shops at Wailea. Just a short drive south, you could spend a day on Makena Beach - voted one of Maui’s top beaches—where your options include riding powerful waves on a surfboard, building sandcastles with your kids, or catching a stunning sunset over the Pacific Ocean.

Continue the ocean-themed fun with some snorkeling around the colorful reef just offshore at La Perouse Bay, three miles south of Makena Beach, where you’re sure to glimpse a huge variety of sea life. If you’re in the mood to explore on land, head inland for an unforgettable hike in the Haleakala crater 57 miles northeast – and don’t forget that camera to snap incredible pictures above the clouds from the Haleakala Observatory.

With world-class beaches and outdoor activities for all ages, this tropical island is a first-rate destination for family fun. Take the first step toward an amazing Hawaiian vacation—reserve your stay at one of our South Maui vacation rentals today!

Discover South Maui


5 Tips for an Amazing Haleakala Sunrise Excursion

Nearby destinations

Maui   |   Haleakalā National Park   |   Maalaea Bay   |   Maui Kamaole - Kihei, HI   |   Kihei Akahi   |   Mana Kai Maui Resort - Kihei, HI   |   Hale Kamaole - Kihei, HI   |   Hale Kai O Kihei   |   Maui Banyan - Kihei, HI   |   Kamaole Sands - Kihei, HI   |   Kihei Ali'i Kai   |   Wailea Grand Champions   |   Maui Parkshore - Kihei, HI   |   Wailea Ekahi Village   |   Wailea   |   Kihei   |   Hawaii
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