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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

Compare 36 Villas in Kahoolawe with updated reviews, rates, and availability.

~ This Is Wailea Living ~
Point of interest

~ This Is Wailea Living ~

10.0 out of 10, Exceptional, (120)
"We really enjoyed our stay in this condo. It was clean and the primary bed was very comfortable. Communication with the host was smooth and efficient. The AC worked great. Beach/pool towels and portable chairs were provided, which was great. As a note, though, I would have really appreciated a cooler and umbrella for the beach. I’d definitely recommend this place to a couple or small family. "
~ This Is Wailea Living ~
Hula On In to Beach House Chic Style, Click the Video tour below!
Outdoor pool

Hula On In to Beach House Chic Style, Click the Video tour below!

10.0 out of 10, Exceptional, (129)
"We loved the condo! Really cleaning well organized. Great space, location and amenities. It has everything you need for a great get away. Groceries, restaurants and beautiful all within 5 min. Thank you for your home away from home."
Hula On In to Beach House Chic Style, Click the Video tour below!
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Outdoor pool, an infinity pool

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

10.0 out of 10, Exceptional, (72)
"We felt so removed from all the hustle bustle of daily life. Our villa was amazing. It had everything we needed and more. We all had such a good time. "
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102
Pool

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

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

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
Gated 2-story beach house with big yard
Exterior detail

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (49)
"Very close to the beach. Very private with beautiful landscaping. Well supplied with all the beach equipment you'd need. Spacious and comfortable for our group. Walkable to some good food, snorkeling, boogie boarding and sun sets! "
Gated 2-story beach house with big yard
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
Exterior

RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS

10.0 out of 10, Exceptional, (186)
"Amazing family vacation!"
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
A waterfall pool

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

9.6 out of 10, Exceptional, (53)
"Overall this property was perfect. Had everything we needed for our family vacation (6 adults, 3 children). Property was clean, located close to pool and beach, shopping close by, we’d definitely stay here again in the future. "
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.
Outdoor pool

Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.

9.8 out of 10, Exceptional, (55)
"Absolutely stunning property. Private pool, love birds and other birds galore. Property is as listed. Watch the whales from the pool deck. We hung out at the pool all the time. Totally private. Terri was wonderful to work with. She kept in touch during our stay. She also stocked our suite with bananas, mango and other treats. The outside shower is to die for. "
Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.
5 Star Ocean View, Beach House Chic, Click the Video tour below!
Outdoor pool

5 Star Ocean View, Beach House Chic, Click the Video tour below!

10.0 out of 10, Exceptional, (86)
"We are so pleased to give this condo and its host the highest rating. The condo location is walkable to excellent coffee, shopping, restaurants and a upscale grocery market. It is in a very quiet and relaxing area of the complex, we enjoyed watching the sunset on the lanai. All the little things that matter like comfy pillows, great water pressure and a spacious and clean environment were on point. Hope to return - Aloha."
5 Star Ocean View, Beach House Chic, Click the Video tour below!
Spectacular 3rd Row Villa at Ho'olei with Ocean Views
Pool

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

10.0 out of 10, Exceptional, (55)
"We had an amazing time. Will be coming back again! "
Spectacular 3rd Row Villa at Ho'olei with Ocean Views
Puamana Retreat by Gather: Oceanfront 3BR w/ Lanai & Resort Amenities in Lahain
Property grounds

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

Puamana Retreat by Gather: Oceanfront 3BR w/ Lanai & Resort Amenities in Lahain
AMAZING LOCATION in the HEART of WAILEA!! WBV H102!
Pool

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!
Oceanview Penthouse, sleeps up to 16 guests!
Beach nearby

Oceanview Penthouse, sleeps up to 16 guests!

9.4 out of 10, Exceptional, (15)
"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
Outdoor pool, a heated pool

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
Aloha Villas Resort | 12 Bed, 12.5 Bath
Outdoor dining

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
CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!
Beach nearby, sun loungers, beach towels

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!
Rare Find! Ocean and Beach Front Cottage!
On the beach

Rare Find! Ocean and Beach Front Cottage!

The price is SAR 1,767
SAR 3,897 total
includes taxes & fees
29 Apr - 30 Apr
Rare Find! Ocean and Beach Front Cottage!
New Listing! RARE, DIRECT OCEANFRONT Wailea Beach Villa B202
Pool

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
Exterior

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (520)
"Excellent stay and wonderful place to vacation with access to the pool and the beach! Our condo was outstanding!"
Wailea Ekahi - CoralTree Residence Collection
Sugar Beach Resort
Outdoor pool

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1047)
"The view was beautiful from the balcony as it was right on the beach. Unit was very clean and had everything you needed for an enjoyable vacation. The king bed was comfortable and it is always nice to have a washer & dryer. The one recommendation I would make would be to upgrade the living room furniture as it is very uncomfortable and outdated. "
Sugar Beach Resort
Wailea Grand Champions - CoralTree Residence Collection
2 outdoor pools

Wailea Grand Champions - CoralTree Residence Collection

3.0 star property
9.0 out of 10, Wonderful, (700)
"Convenient location, good sized unit, clean and in good condition and walkable location."
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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