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

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (44)
"The house is amazing, providing the perfect atmosphere for quality time with my family. All slept well, felt at home and enjoyed every moment. Thank you!"
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

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

9.6 out of 10, Exceptional, (48)
"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!

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

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

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

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

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!

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!

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

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

10.0 out of 10, Exceptional, (67)
"This our favorite place to stay on Maui. Lovely, well-maintained condo with an ocean view and quick walk to pools and the beach. We spent some time every day at the adult pool, which is a quiet, beautiful setting. The gym was well-equipped. Linda was a responsive and terrific host. Despite a series of thunderstorms with 70mph winds that knocked out power our last night, we can't wait to return!"
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

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!

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

10.0 out of 10, Exceptional, (25)
"This place was exceptional - beautiful home, well appointed, location could not be better! We loved walking to the beach and so many terrific restaurants. Appreciated having some beach equipment there (few beach chairs, one small umbrella, couple of snorkel masks). Pool was also lovely and relaxing - not a zoo like at the resorts. Lots of great space for our family of 8 (all adults). Easy check in. Geoff was very responsive and helpful. Would love to stay here again!!"
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY

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

9.8 out of 10, Exceptional, (61)
"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!"
AMAZING LOCATION in the HEART of WAILEA!! WBV H102!

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, (53)
"The location was wonderful; walking distance to the beach, restaurants, and shops. The photos represent the property well. The kitchen was well stocked, including olive oils, salt, pepper, cleaning products and trash liners. Loads of towels were offered too. The sheets and othering bedding were great quality. All the major appliances worked well and the washing machine came in handy for the family. The only criticism would be the cleanliness of the bathroom rug in the master. Overall, it is a...
Spectacular 3rd Row Villa at Ho'olei with Ocean Views

Special Promo at Ho'olei 55-3 - Book Now and Save!

9.8 out of 10, Exceptional, (51)
"Clean, beautiful area and property. Highly recommended. Easy access to public beach."
Special Promo at Ho'olei 55-3 - Book Now and Save!

Updated Ho'olei Villa 24-1! Spacious and Luxurious!

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...
Updated Ho'olei Villa 24-1! Spacious and Luxurious!

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!

New Listing! RARE, DIRECT OCEANFRONT Wailea Beach Villa B202

10.0 out of 10, Exceptional, (2)
"We stayed 10 days and had a great time. The location is perfect to keep everyone busy and still be able to chill out at the pool. Our 2nd time at the property. Highly recommend the location. "
New Listing! RARE, DIRECT OCEANFRONT Wailea Beach Villa B202
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

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (506)
"Loved everything. The beach/pool area was great with the pavilion to hang out in. "
Wailea Ekahi - CoralTree Residence Collection

Wailea Grand Champions - CoralTree Residence Collection

3.0 star property
9.0 out of 10, Wonderful, (685)
"The only complaint I have is that the pool wasn't kid friendly. We had 5 little girls with us, and in the evening, we were always asked to leave the facility because they were too noisy. Also, the hot tub was cold for several days in a row. "
Wailea Grand Champions - CoralTree Residence Collection

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very Good, (718)
"Property is very close to the ocean with a nice beach. "
Maui Beach Vacation Club
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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