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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 38 Villas in Kahoolawe with updated reviews, rates, and availability.

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, (75)
"Our family vacation PH H101 this home is the best . Linda is a great host always answered our request we will be back "
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Gated 2-story beach house with big yard
Exterior detail

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (57)
"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
~ This Is Wailea Living ~
Outdoor pool

~ This Is Wailea Living ~

10.0 out of 10, Exceptional, (122)
"Great location. Everything just as advertised"
The price is AED 1,010
AED 2,297 total
includes taxes & fees
3 Jun - 4 Jun
~ This Is Wailea Living ~
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, (54)
"Property is totally amazing. Wonderful location, amenities and cleanliness. Our family loved our stay. We will return. "
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Rare Find! Ocean and Beach Front Cottage!
On the beach

Rare Find! Ocean and Beach Front Cottage!

10.0 out of 10, Exceptional, (2)
"Over all great time. You will loose your parking spot almost every time you leave as it is next to beach access."
Rare Find! Ocean and Beach Front Cottage!
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, (189)
"Nice property, great views. Would stay again. "
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
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, (131)
"Condo was very clean, comfortable, and just perfect for our week vacation in Maui with our teen children. Would highly recommend! "
Hula On In to Beach House Chic Style, Click the Video tour below!
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)
"We had a wonderful vacation and this location was perfect. After visiting multiple areas in Maui, we decided we like this area best "
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
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, (56)
"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
Wailea Beach Villas M312: Your Hawaiian Paradise
Pool

Wailea Beach Villas M312: Your Hawaiian Paradise

10.0 out of 10, Exceptional, (12)
"Wonderful views and beach!"
Wailea Beach Villas M312: Your Hawaiian Paradise
Panoramic Ocean Views at Wailea Beach Villas I503
On the beach

Panoramic Ocean Views at Wailea Beach Villas I503

10.0 out of 10, Exceptional, (74)
"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."
Panoramic Ocean Views at Wailea Beach Villas I503
I.P.M PRESENTS: VILLA E101 - PRIVATE POOL + YARD. FLEXIBLE CANCELATION POLICY
Interior

I.P.M PRESENTS: VILLA E101 - PRIVATE POOL + YARD. FLEXIBLE CANCELATION POLICY

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay at the Villas. Everything was as advertised. Wailea is a great area to stay with access to so many things within walking distance."
I.P.M PRESENTS: VILLA E101 - PRIVATE POOL + YARD. FLEXIBLE CANCELATION POLICY
Renovated 2BR/2BA Wailea Ekahi 26A Ground-Floor Condo with Ocean and Sunset View
Pool

Renovated 2BR/2BA Wailea Ekahi 26A Ground-Floor Condo with Ocean and Sunset View

10.0 out of 10, Exceptional, (59)
"Everything was perfect all the way around."
Renovated 2BR/2BA Wailea Ekahi 26A Ground-Floor Condo with Ocean and Sunset View
I.P.M PRESENTS: HOOLEI 99-2 BRAND NEW REMODEL - WOW! FLEXIBLE CANCELATION POLICY
Pool

I.P.M PRESENTS: HOOLEI 99-2 BRAND NEW REMODEL - WOW! FLEXIBLE CANCELATION POLICY

9.8 out of 10, Exceptional, (15)
"Loved our stay in this roomy well appointed home in a well located quiet Wailea neighborhood. Spectacular 180 degree ocean view."
I.P.M PRESENTS: HOOLEI 99-2 BRAND NEW REMODEL - WOW! FLEXIBLE CANCELATION POLICY
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)
"It was a great stay and the host was very responsive with any questions we may have had. Aloha and mahalo"
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY
Ultimate Luxury Chef's Kitchen Soaking Tub and Private Lanai in Stunning Villa!
Pool

Ultimate Luxury Chef's Kitchen Soaking Tub and Private Lanai in Stunning Villa!

9.8 out of 10, Exceptional, (52)
"Family vacation "
Ultimate Luxury Chef's Kitchen Soaking Tub and Private Lanai in Stunning Villa!
Escape to Ho'olei – Ocean Views & Luxe Comfort
Pool

Escape to Ho'olei – Ocean Views & Luxe Comfort

9.6 out of 10, Exceptional, (74)
"Beautiful villa with all of the accommodations needed for a wonderful holiday. Perfectly located to get to all that Wailea offers."
Escape to Ho'olei – Ocean Views & Luxe Comfort
Private Ocean Front at Wailea Beach Villas B102
Pool

Private Ocean Front at Wailea Beach Villas B102

10.0 out of 10, Exceptional, (27)
"The unit and property were beautiful. Very spacious and loved being so close to the ocean. Hope to be back again soon. "
Private Ocean Front at Wailea Beach Villas B102
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, (87)
"Great host had a lovely time thank you so much!"
5 Star Ocean View, Beach House Chic, Click the Video tour below!
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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