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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 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, (74)
"Lovely condominium with nice appointments The kitchen was well stocked. Bedrooms were spacious. Great patio with outdoor dining tableIt was a bit of a hike to the beach. All in all a great experience "
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Private Ocean Front at Wailea Beach Villas B102
Pool

Private Ocean Front at Wailea Beach Villas B102

10.0 out of 10, Exceptional, (26)
"I cannot say enough about this villa and our experience. The villa is beautiful, the location is perfect and the service was excellent. We loved our private plunge pool and being steps away from the quiet adult pool. This unit is also very close to the beach, where they will set up umbrellas and lounge chairs for you. The beach itself is lovely with soft sand and clear water. Sea turtles would come visit every day. Another huge plus for us was that the property was within walking distance of...
Private Ocean Front at Wailea Beach Villas 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
Exquisite Oceanview Villa with Resort Amenities in Gated Community
Pool

Exquisite Oceanview Villa with Resort Amenities in Gated Community

10.0 out of 10, Exceptional, (62)
"Property is greatView great "
Exquisite Oceanview Villa with Resort Amenities in Gated Community
Gated 2-story beach house with big yard
Exterior detail

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (52)
"Our family of 6 thoroughly enjoyed this house. Situated within walking distance of a great beach and close to plenty of shopping, you couldn’t ask for a better location. The property is fenced in which allows for privacy and a sense of security. There are plenty of amenities in the house including surfboards, boogie boards, chairs and an umbrella for the beach, bikes a ping pong table, a hammock and much more. We had a great time and would stay there again in a heartbeat!"
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, (187)
"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, (55)
"This was a beautiful home and excellent location for us. There were six adults in our family and we each had our own room and bathroom, which was very nice. The air conditioner work nicely and the management team was very prompt that we had. The pool was very close and nice to sit by and we could walk to several beaches nearby. The property had chairs and towels, and a wagon which was super sweet to use. It was well stocked with items that we needed to use for a simple cooking or paper...
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, (56)
"5 star property with a 5 star hostess. We had a peaceful and relaxing visit and will be back"
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

10.0 out of 10, Exceptional, (1)
"Four adults and two kids had a wonderful stay. Kitchen had everything we needed. Kids loved the pool. Adults enjoyed the beach and the view. We all appreciated the beach toys and used them well "
Puamana Retreat by Gather: Oceanfront 3BR w/ Lanai & Resort Amenities in Lahain
Exquisite Spacious Wailea Beach Villas H102
Pool

Exquisite Spacious Wailea Beach Villas H102

9.8 out of 10, Exceptional, (64)
"My family and I stay in these condos about once a year. We stay in this particular condo for the cleanliness and access to laundry and kitchen for the kids. It really is a great place for a busy family like ours who are always running up and down from the beach. If you want a place with more amenities- nicer soaps, towels,fluffy beds, access to storage for beach chairs etc - maybe look elsewhere? But if you are a young family on the go this place is great!"
Exquisite Spacious Wailea Beach Villas H102
Oceanview Penthouse, sleeps up to 16 guests!
Beach nearby

Oceanview Penthouse, sleeps up to 16 guests!

9.4 out of 10, Exceptional, (15)
"Perfect Maui getaway. Went for my Bach party with 10 of my best friends. Fabulous neighboorbood. Great safe location. Close to all the beaches and luxury restaurants. "
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 1,658
SAR 3,788 total
includes taxes & fees
8 May - 9 May
Rare Find! Ocean and Beach Front Cottage!
Exquisite Oceanfront Wailea Beach Villas B202
Pool

Exquisite Oceanfront Wailea Beach Villas 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. "
Exquisite Oceanfront Wailea Beach Villas 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

Maui Beach Vacation Club
Suite, 2 Bedrooms | Living area | TV

Maui Beach Vacation Club

2.5 star property
8.4 out of 10, Very Good, (737)
"Great experience perfect for this time of year in the early spring clean everything we needed. It just doesn’t have air conditioning so in the summer it would be too hot to stay there. The staff was amazing and very sweet."
Maui Beach Vacation Club
Wailea Ekahi - CoralTree Residence Collection
Exterior

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (532)
"Our unit was clean, location was great.Main pool was right at the beach, kids had fun. Only drawback, you may have few minutes walk to the pool. "
Wailea Ekahi - CoralTree Residence Collection
Sugar Beach Resort
Outdoor pool

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1054)
"We enjoyed our stay.Will Visit again"
Sugar Beach Resort
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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