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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Villas in Wailea-Makena

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, (81)
"Everything was wonderful… thank you so much Linda."
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
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, (55)
"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
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
Wailea Beach Villas M312: Your Hawaiian Paradise
Enjoy stunning ocean views from this beachfront property, surrounded by tall palm trees and a well-manicured lawn.

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
~ 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, (128)
"Fantastic property."
The price is NZ$923
includes taxes & fees
4 Sept - 5 Sept
~ This Is Wailea Living ~
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
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!
Escape to Ho'olei – Ocean Views & Luxe Comfort
Relax by the pool surrounded by lush vegetation and a cascading waterfall.

Escape to Ho'olei – Ocean Views & Luxe Comfort

9.6 out of 10, Exceptional, (75)
"Property was as described, close proximity to all that we needed, would definitely stay again "
Escape to Ho'olei – Ocean Views & Luxe Comfort
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
Exquisite Spacious Wailea Beach Villas H102
Relax by the serene pool surrounded by lush greenery and palm trees, with a clear view of the ocean in the background.

Exquisite Spacious Wailea Beach Villas H102

9.8 out of 10, Exceptional, (64)
"We had a great time staying here. The place had plenty of room and great amenities. Very family friendly and still had quiet places for adults only."
Exquisite Spacious Wailea Beach Villas H102
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, (18)
"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
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
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
I.P.M PRESENTS: VILLA E301 - STUNNING NEW REMODEL + FLEXIBLE CANCELATION POLICY
Relax in a room with a comfortable seating area and lush greenery views.

I.P.M PRESENTS: VILLA E301 - STUNNING NEW REMODEL + FLEXIBLE CANCELATION POLICY

10.0 out of 10, Exceptional, (1)
"Loved the location! right next to shopping dining loved adult pool with another pool for children property”feels” smaller beautiful patios with waterfalls running nearby the property landscaping is lush and beautiful"
I.P.M PRESENTS: VILLA E301 - STUNNING NEW REMODEL + FLEXIBLE CANCELATION POLICY
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)
"Everything was exceptional. The music from the Marriott next store played too loud and late a couple nights thought"
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
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, (132)
"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!
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!
Tropical Luxury Villa Indoor-Outdoor Living, Gourmet Kitchen and Spa Bathrooms!
Relax by the serene pool surrounded by lush tropical plants and a natural rock formation with a cascading waterfall.

Tropical Luxury Villa Indoor-Outdoor Living, Gourmet Kitchen and Spa Bathrooms!

9.8 out of 10, Exceptional, (38)
"Ho’olei is a beautiful property. The Villa needs updating. "
Tropical Luxury Villa Indoor-Outdoor Living, Gourmet Kitchen and Spa Bathrooms!
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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Top Wailea-Makena Hotel Reviews

Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

10/10 Excellent
"I can tell that the owner invests to keep the quality high vs other places I have stayed on Maui "
David 3-night trip
Posted 2 days ago
Mana Kai Maui- Official Onsite Rental