Search Villas in South Maui

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Compare 25 Villas in South Maui with updated reviews, rates, and availability.

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (40)
"We had a great time in Kihei and the place was perfect for my family. The yard was amazing and we could walk to the beach!"
Gated 2-story beach house with big yard

Special Promotions! Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-

9.6 out of 10, Exceptional, (66)
"Everything was fabulous from our contact with Monica to get us checked in and deliver packages shipped from home to the beautiful accommodation to the pool to the location. We will be back with our family of 8 very soon."
Special Promotions! Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-

EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102

10.0 out of 10, Exceptional, (24)
"The unit and property were beautiful. Very spacious and loved being so close to the ocean. Hope to be back again soon. "
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102

Stunning 3BD/4BA Andaz Villa! Huge Private Yard with Pool! Modern Beach Elegance

10.0 out of 10, Exceptional, (2)
"This villa was beautifully decorated, super clean and very convenient yet private and quiet. CB Island vacations was so attentive, and knowing it was my birthday, rewally surprised us at our welcome . Everything was perfect...really. Barbara"
Stunning 3BD/4BA Andaz Villa! Huge Private Yard with Pool! Modern Beach Elegance

Oceanview Penthouse, sleeps up to 16 guests!

9.6 out of 10, Exceptional, (13)
"Great place, a perfect destination for a family trip"
Oceanview Penthouse, sleeps up to 16 guests!

Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!

9.6 out of 10, Exceptional, (47)
"The property was very nice. Great location. Very clean. "
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!

Aloha Villas Resort | 12 Bed, 12.5 Bath

9.8 out of 10, Exceptional, (43)
"No detail, communication or service was less than spectacular. From the fully equipped villas to games and lush greenery, we enjoyed our home in paradise for two weeks. Thank you to Jude and Mary for promptly responding to our needs throughout our stay."
Aloha Villas Resort | 12 Bed, 12.5 Bath

Spectacular 3rd Row Villa at Ho'olei with Ocean Views

10.0 out of 10, Exceptional, (51)
"Communication prior to going was easy and thorough. Condo was lovely and clean and well equipped. Property grounds were beautiful and very well maintained, with a gorgeous pool and gym. If issues came up response was quickly handled...there are many battery operated blinds in the home that need charging prior to guests' arrival. One of the blinds didnt work and it was fixed that evening. The view is spectacular from the upper sitting area! Property itself is up a hill, across from the...
Spectacular 3rd Row Villa at Ho'olei with Ocean Views

Ho'olei 55-3 gorgeous upscale living!

9.8 out of 10, Exceptional, (51)
"Clean, beautiful area and property. Highly recommended. Easy access to public beach."
Ho'olei 55-3 gorgeous upscale living!

Free Night! Free Late Check Out! Free Future Stay!

10.0 out of 10, Exceptional, (72)
"We have stayed in Wailea many times and at this property(not this unit) before as well. It was almost perfect with the exception that my wife would like to see bathrobes . Whatever . It was perfect. "
Free Night! Free Late Check Out! Free Future Stay!

Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

10.0 out of 10, Exceptional, (51)
"Wrong entry code for property gate. Snuck in with a car who went around us. Never received a “personal code” to actually enter the unit. Waited in garage for a return call that thankfully granted us access Everything was great after that except that only one card worked for the unit out stay. "
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

10.0 out of 10, Exceptional, (65)
"We were there for our 50th anniversary with family- 4 adults and 2 children! Great location, beautiful condo "
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY

10.0 out of 10, Exceptional, (23)
"We love the house. It was perfect for the family. The only downside was the master bedroom is very warm compared to the rest of the house. Also, there is mold in the master bathroom shower but overall it was a great place to stay. The pool is very nice And the location can’t be beat. "
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY

Free Night! AMAZING LOCATION in the HEART of WAILEA!! WBV H102!

9.8 out of 10, Exceptional, (60)
"We were there for a conference next door at the Marriott but staying in this unit (for the second year in a row) gave us a perfect retreat from the day-to-day commotion of the venue. Always impeccably maintained and supplied!"
Free Night! AMAZING LOCATION in the HEART of WAILEA!! WBV H102!

Book 5 Nights, Get 6th Free + Late Check-Out!

10.0 out of 10, Exceptional, (8)
"This was the best location, easy to get to beach and mall"
Book 5 Nights, Get 6th Free + Late Check-Out!

Redesigned Penthouse! WBV J106

10.0 out of 10, Exceptional, (63)
"WBV is a great property and location - everything is perfectly maintained and the entire visit was incredibly smooth. Really impressed and would absolutely book at this location again. "
Redesigned Penthouse! WBV J106

Book 5 nights get 1 free! Ho'olei Villa 24-1!

10.0 out of 10, Exceptional, (53)
"This townhome is a real gem. The floor plan is open and the rooms are spacious. The kitchen is well appointed. The beds were comfortable. The showers were good with fast supply of hot water. The grill was clean and functional. Everything was in good condition. There is an elevator which was an asset. The townhome is located within one block of the pool and gym and 4-5 blocks from Wailea beach. A small grocery store is across the street and Kihei, which has more stores and restaurants, is a short...
Book 5 nights get 1 free! Ho'olei Villa 24-1!

Panoramic Ocean Views! - Luxury Villa! - Owner Direct!

10.0 out of 10, Exceptional, (70)
"Our villa was very clean and beautiful with a nice view of the ocean. The staff on the property was extremely helpful and courteous. The location can’t be beat as it’s a short walk to the beach and The Shops at Wailea. "
Panoramic Ocean Views! - Luxury Villa! - Owner Direct!

New Listing! RARE, DIRECT OCEANFRONT Wailea Beach Villa B202

10.0 out of 10, Exceptional, (1)
"Lovely residence. Beautiful views of water and beach."
New Listing! RARE, DIRECT OCEANFRONT Wailea Beach Villa B202

Villas By The Cove, Villa 3 · Step to White-Sand Beach

9.8 out of 10, Exceptional, (76)
"The villas are super quaint with a bungalow feel and well takin care of. We loved sitting out by the pool and talking to the other guests. The privacy of the fenced in and gated property was really nice and felt secure. Id definitely recommend staying here and I look forward to our next trip there. "
The price is ¥49,023
¥95,265 total
includes taxes & fees
Dec 1 - Dec 2
Villas By The Cove, Villa 3 · Step to White-Sand Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Snorkeling, Swimming and Sunsets! Steps from the beach!

10.0 out of 10, Exceptional, (124)
"This is our second trip with my three kids. This is a unique and wonderful property. Perfect for families!"
Snorkeling, Swimming and Sunsets! Steps from the beach!

Makena Surf by Coldwell Banker Island Vacations

3.0 star property
Makena Surf by Coldwell Banker Island Vacations

Spectacular Ocean Views - Beautifully Renovated Condo - 2 New Pools

10.0 out of 10, Exceptional, (96)
"This condo was perfect for our family! We loved the location and amenities of Makena Surf -- especially the short swim to wonderful snorkeling. Everything was clean and the owners had thought of everything, even a garlic press in the kitchen, boogie boards, etc.! The beds are comfortable, the view is breathtaking, location of this condo is very quiet but central at the same time, and the owner, Jayne, is extremely helpful and responsive. We can't wait to come back some day!"
Spectacular Ocean Views - Beautifully Renovated Condo - 2 New Pools
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.