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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Villas in Kihei

Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Relax by the serene pool surrounded by lush greenery and palm trees, with a soothing waterfall and comfortable deck seating.

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

10.0 out of 10, Exceptional, (79)
"Everything was wonderful… thank you so much Linda."
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
Stunning two-story residence with a spacious balcony and beautifully manicured lawn.

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

10.0 out of 10, Exceptional, (194)
"Amazing family vacation!"
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
~ This Is Wailea Living ~
Walk along the paved path to the wide, sandy beach, surrounded by lush greenery and tall palm trees.

~ This Is Wailea Living ~

10.0 out of 10, Exceptional, (127)
"It was great place to stay , close to beach etc."
~ This Is Wailea Living ~
5 Star Ocean View, Beach House Chic, Click the Video tour below!
Relax by the pool surrounded by lush greenery and palm trees.

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

10.0 out of 10, Exceptional, (88)
"Great host had a lovely time thank you so much!"
5 Star Ocean View, Beach House Chic, Click the Video tour below!
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Relax by the resort pool surrounded by a scenic waterfall and lounge chairs.

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
Gated 2-story beach house with big yard
Stunning traditional architecture surrounded by lush greenery and a beautifully maintained entrance.

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (62)
"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
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
Relax by the serene pool surrounded by lush tropical plants and palm trees, with a waterfall cascading down a rocky ledge.

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

9.6 out of 10, Exceptional, (60)
"This condo was perfect! Very clean and accommodating for our group! The host was very quick to respond and the condo was in a great location! We will be back"
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
Relax by the resort pool surrounded by lush tropical vegetation and a natural rock formation with a cascading waterfall.

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

10.0 out of 10, Exceptional, (57)
"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
Relax by the serene pool surrounded by lush vegetation and palm trees, with lounge chairs and umbrellas providing shaded seating.

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
Rare Find! Ocean and Beach Front Cottage!
Enjoy a serene ocean view with gentle waves and a rugged shoreline perfect for exploration.

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!
Luxury Villa Steps from Wailea Beach with Resort Amenities and Stunning Upgrades
Relax by the resort's pool surrounded by palm trees and a rocky landscape.

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

10.0 out of 10, Exceptional, (55)
"We met up with our family fromAustralia and had a wonderful time here in Maui. The condo was very well maintained and well stocked which made for a pleasant experience. Would highly recommend. "
Luxury Villa Steps from Wailea Beach with Resort Amenities and Stunning Upgrades
Panoramic Ocean Views! - Luxury Villa! - Owner Direct!
Relax and socialize in this inviting balcony area with comfortable seating, a grill, and stunning views of the resort.

Panoramic Ocean Views! - Luxury Villa! - Owner Direct!

10.0 out of 10, Exceptional, (71)
"Wonderful accommodations, great location and friendly staff!"
Panoramic Ocean Views! - Luxury Villa! - Owner Direct!
Bright and Luxurous Wailea Beach Villas I204
Relax by the oceanfront pool surrounded by palm trees and a distant mountain range.

Bright and Luxurous Wailea Beach Villas I204

10.0 out of 10, Exceptional, (61)
"A beautiful villa, great views and plenty of amenities. Would definitely come back!"
Bright and Luxurous Wailea Beach Villas I204
I.P.M PRESENTS: VILLA E101 - PRIVATE POOL + YARD. FLEXIBLE CANCELATION POLICY
Relax in the living area with a potted plant, two armchairs, and a small table with a lamp.

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
I.P.M PRESENTS: HOOLEI 99-2 BRAND NEW REMODEL - WOW! FLEXIBLE CANCELATION POLICY
Surrounded by lush tropical vegetation and a serene waterfall, this resort offers a tranquil escape amidst nature.

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

9.6 out of 10, Exceptional, (17)
"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: VILLA E102 - PRIVATE POOL + YARD. FLEXIBLE CANCELATION POLICY
Relax by the pool surrounded by lush greenery and palm trees, with a covered patio area perfect for dining or unwinding.

I.P.M PRESENTS: VILLA E102 - PRIVATE POOL + YARD. FLEXIBLE CANCELATION POLICY

9.2 out of 10, Wonderful, (11)
"Everything is too notch at the Villas. We brought our family here for Thanksgiving and had two Villas side by side. We had the best time! The beach is so close and many yummy restaurants in the area. We want to come back every year!!!"
I.P.M PRESENTS: VILLA E102 - PRIVATE POOL + YARD. FLEXIBLE CANCELATION POLICY
Luxury Oceanview Wailea Retreat [Hōkū Hale]
Shop and dine in style amidst lush surroundings and beautifully landscaped gardens.

Luxury Oceanview Wailea Retreat [Hōkū Hale]

The price is AU$2,035
includes taxes & fees
8 Aug - 9 Aug
Luxury Oceanview Wailea Retreat [Hōkū Hale]
Ho'olei Garden View by Coldwell Banker Island Vacation
Pool

Ho'olei Garden View by Coldwell Banker Island Vacation

2.0 star property
Ho'olei Garden View by Coldwell Banker Island Vacation
Private Ocean Front at Wailea Beach Villas B102
Relax by the oceanfront pool surrounded by lush vegetation and natural rock formations.

Private Ocean Front at Wailea Beach Villas B102

10.0 out of 10, Exceptional, (29)
"Great location for adult children, aging parent alike"
Private Ocean Front at Wailea Beach Villas B102
Exquisite Oceanview Villa with Resort Amenities in Gated Community
Relax by the pool surrounded by lush tropical plants and a cascading waterfall.

Exquisite Oceanview Villa with Resort Amenities in Gated Community

10.0 out of 10, Exceptional, (67)
"Our family enjoyed our time here - nice memories"
Exquisite Oceanview Villa with Resort Amenities in Gated Community
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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