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Compare Villas in Kahoolawe with updated reviews, rates, and availability.

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (46)
"The house was perfect for our visit with family. There were multiple areas inside and out to relax or spend time in. The grounds were beautiful...even one orchid blooming. "
Gated 2-story beach house with big yard

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

10.0 out of 10, Exceptional, (25)
"Positive"
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102

Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4

9.6 out of 10, Exceptional, (67)
"Beautiful villa with all of the accommodations needed for a wonderful holiday. Perfectly located to get to all that Wailea offers."
Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4

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

9.6 out of 10, Exceptional, (50)
"We had a conference at the Grand Wailea and were bringing our adult children. This rental is very close to the hotel for a go between to attend the conference and catch up with our children at the end of the day. We stayed at the rental with them when the conference was over. Short walk to the shops and beach!Great layout for everyone to have their own space. "
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!

Puamana Retreat by Gather: Oceanfront 3BR w/ Lanai & Resort Amenities in Lahain

Puamana Retreat by Gather: Oceanfront 3BR w/ Lanai & Resort Amenities in Lahain

Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3

10.0 out of 10, Exceptional, (62)
"Property is greatView great "
Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3

Redesigned Penthouse! WBV J106

10.0 out of 10, Exceptional, (64)
"We really enjoyed our stay and were pleased witj the updated unit, condition, and cleanliness. It was plenty of room for our family of 4 adults. Fully stocked chef’s kitchen. The staff is nice and we got a personal on site greeting from the rental manager. Mark at the gate is very friendly. "
Redesigned Penthouse! WBV J106

Luxury 3-Bedroom Wailea Beach Villa M312

10.0 out of 10, Exceptional, (9)
"This was the best location, easy to get to beach and mall"
Luxury 3-Bedroom Wailea Beach Villa M312

Wailea Beach Villas I503! 3 bedroom 5th floor penthouse!

10.0 out of 10, Exceptional, (73)
"Allison, Luxury Manager from the Coldwell staff, was unbelievably helpful in getting us checked in, and helping to accommodate some special needs for wheelchair storage.The rental itself was beautiful, exactly as depicted in the listing. The Beach Villas are a stones through from the shore, and the resort staff were very friendly and accommodating.If you are planning a stay on the Kihei/Wailea side, I would recommend this rental."
Wailea Beach Villas I503! 3 bedroom 5th floor penthouse!

I.P.M PRESENTS: VILLA E301 - STUNNING NEW REMODEL + FLEXIBLE CANCELATION POLICY

10.0 out of 10, Exceptional, (1)
"Loved the location! right next to shopping dining loved adult pool with another pool for children property”feels” smaller beautiful patios with waterfalls running nearby the property landscaping is lush and beautiful"
I.P.M PRESENTS: VILLA E301 - STUNNING NEW REMODEL + FLEXIBLE CANCELATION POLICY

Oceanview Penthouse, sleeps up to 16 guests!

9.4 out of 10, Exceptional, (14)
"Great place, a perfect destination for a family trip"
Oceanview Penthouse, sleeps up to 16 guests!

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

10.0 out of 10, Exceptional, (26)
"This property was exactly as described and complete perfection as it related to housing all of our family members. The grounds are beautiful. The pool is gorgeous. The location for us was exactly where we wanted to be and just across the street from the beach. We did have some street noise coming from behind the patio but it wasn't terribly intrusive. The kitchen was well stocked with dishes and utensils as well as small appliances. The Furnishings are modern which included a fair amount of...
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY

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

10.0 out of 10, Exceptional, (70)
"Linda’s place is beautiful! The location is great, and the condo is big, with 2 master suites plus another bedroom this condo is the perfect layout for 2 couples/ family’s. Big beautiful deck with a bbq. We loved staying there and would forsure book again! "
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

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

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

10.0 out of 10, Exceptional, (53)
"My family and I planned this trip back in March 2024 and reserved this property in Ho'olei.Right from the initial reservation process and first payment installment, the interaction with Matthew was excellent and seamless. Matthew was responsive and very helpful.The unit at Ho'olei was remarkable, well located within the property, and most importantly, was extremely clean when we checked in. There was a small welcome gift which was appreciative. The unit was very well equipped with all we needed,...
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

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

9.8 out of 10, Exceptional, (62)
"Great stay for my wife and two daughters. Property was perfect and everything went smoothly. Monique helped us check in and she was outstanding. Five Stars for her too! Thank you for a wonderful vacation. "
AMAZING LOCATION in the HEART of WAILEA!! WBV H102!

CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!

9.6 out of 10, Exceptional, (64)
"Great stay at Tamara's condo. The location is fantastic, walking distance to the beach, shops, restaurants and the Wailea beach trail. The condo was well equipped. We easily cooked meals in the kitchen, which had everything we needed. The condo was clean and welcoming. We brought the provided beach chairs and beach towels, to Big Beach. The bathroom had sunscreen and a first aid kit, The band aids came in handy. Having a laundry allowed us to pack light. We really appreciated that Tamara left...
CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!

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

10.0 out of 10, Exceptional, (54)
"We had an amazing time. Will be coming back again! "
Spectacular 3rd Row Villa at Ho'olei with Ocean Views

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

10.0 out of 10, Exceptional, (71)
"The views from this condo are amazing! The penthouse units are farther from the main pool and beach but we think the walk is worth the trade off for the view. The kitchen was very well equipped and having two refrigerators is great especially for a week stay during the holidays. We had a property manager we could contact with any needs or questions and upon check out we did provide her with a list of small maintenance suggestions that needed addressing, however none of the items prevented us...
Panoramic Ocean Views! - Luxury Villa! - Owner Direct!

I.P.M PRESENTS: VILLA C302 - SPECTACULAR NEW REMODEL + GREAT OCEAN VIEW!

10.0 out of 10, Exceptional, (8)
"Love Maui...Have vacationed in Maui over 20+ times. This is a Great place to stay. Centrally located to Wailea Shops and restaurants. Enough room for a family of six. Enjoyed our family time together and staying in a beautiful home, in a beautiful area. "
I.P.M PRESENTS: VILLA C302 - SPECTACULAR NEW REMODEL + GREAT OCEAN VIEW!
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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Other property types in Kahoolawe

Aston Maui Hill

3.0 star property
9.0 out of 10, Wonderful, (779)
"Property was lovely and we especially appreciated the surprise welcome gift that was waiting for us. Pool was well maintained. It felt a little small for the number of units but we never had a problem finding lounges to sit in. "
Aston Maui Hill

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (510)
"Perfect location, comfortable apartment and great view. Coral tree was very responsive to all my needs. "
Wailea Ekahi - CoralTree Residence Collection

Wailea Grand Champions - CoralTree Residence Collection

3.0 star property
9.0 out of 10, Wonderful, (694)
"Great location, remodeled and clean. "
Wailea Grand Champions - CoralTree Residence Collection
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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