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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Browse Select Kahoolawe Villas

~ This Is Wailea Living ~
Sun-loungers, beach towels

~ This Is Wailea Living ~

10.0 out of 10, Exceptional, (125)
"Perfectly located near dining, shopping, golf and beach. Chris was a very solicitous and helpful host. Some features are a little bit dated, but the unit was clean and comfortable. "
The price is £506
includes taxes & fees
22 Jul - 23 Jul
~ This Is Wailea Living ~
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, (77)
"Everything was wonderful… thank you so much Linda."
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
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)
"We come to Maui annually for spring break. This was a great property to use as our base."
Hula On In to Beach House Chic Style, Click the Video tour below!
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
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, (59)
"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!
Luxury Oceanview Wailea Retreat [Hōkū Hale]
Property grounds

Luxury Oceanview Wailea Retreat [Hōkū Hale]

The price is £1,019
includes taxes & fees
30 Jun - 1 Jul
Luxury Oceanview Wailea Retreat [Hōkū Hale]
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
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
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, (66)
"We had a terrific stay with no problems at all."
Exquisite Oceanview Villa with Resort Amenities in Gated Community
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!
Bright and Luxurous Wailea Beach Villas I204
Pool

Bright and Luxurous Wailea Beach Villas I204

10.0 out of 10, Exceptional, (60)
"A beautiful villa, great views and plenty of amenities. Would definitely come back!"
Bright and Luxurous Wailea Beach Villas I204
Redesigned Penthouse! Wailea Beach Villas J106
Pool

Redesigned Penthouse! Wailea Beach Villas J106

10.0 out of 10, Exceptional, (68)
"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! Wailea Beach Villas J106
Luxury Villa Steps from Wailea Beach with Resort Amenities and Stunning Upgrades
Pool

Luxury Villa Steps from Wailea Beach with Resort Amenities and Stunning Upgrades

10.0 out of 10, Exceptional, (55)
"This was an amazing home to stay in. It is close to a variety of beaches and restaurants, and we enjoyed being in the heart of Wailea. The home itself was clean, with comfortable beds and furniture, and had everything we needed for a relaxing vacation (i.e. beach chairs, umbrellas, cooler, laundry) "
Luxury Villa Steps from Wailea Beach with Resort Amenities and Stunning Upgrades
I.P.M PRESENTS: VILLA F101 - PRIVATE POOL + YARD! FLEXIBLE CANCELATION POLICY
A heated pool

I.P.M PRESENTS: VILLA F101 - PRIVATE POOL + YARD! FLEXIBLE CANCELATION POLICY

9.6 out of 10, Exceptional, (22)
"We had two adults and four adult children (early 20's), the layout was great. The location was great too."
I.P.M PRESENTS: VILLA F101 - PRIVATE POOL + YARD! FLEXIBLE CANCELATION POLICY
Panoramic Ocean Views at Wailea Beach Villas I503
Pool

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
Gated 2-story beach house with big yard
Exterior detail

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (58)
"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
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)
"Amazing family vacation!"
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
Rare Find! Ocean and Beach Front Cottage!
On the beach

Rare Find! Ocean and Beach Front Cottage!

9.0 out of 10, Wonderful, (4)
"We stayed a week in this cute beach front cottage. It is central located with walking distance to restaurants, surfing lessons, groceries and shops. The owner/host was easily get in touch with and accommodated us with early check in since we had a very early flight in. The view is beautiful and we watched sunset every day from our lanai. "
Rare Find! Ocean and Beach Front Cottage!
Stunning Koa Resort 3bd Villa with private Jet Spa
TV

Stunning Koa Resort 3bd Villa with private Jet Spa

10.0 out of 10, Exceptional, (4)
"Very nice resort close to beaches and good places to eat, staff was friendly and did reach out during my stay to ask If we needed anything, I would definitely stay here again."
The price is £799
includes taxes & fees
28 Jun - 29 Jun
Stunning Koa Resort 3bd Villa with private Jet Spa
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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