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Wailea Villas Near Grand Wailea
Hoolei at Grand Wailea offers the right blend of privacy, space, and five-star comfort. Designed for families, groups, or luxury-seeking couples, these multi-level villas offer over 3,000 square feet of living space in the heart of South Maui, walking distance to The Shops at Wailea, dining, and beaches.
Each Hoolei villa includes three bedrooms, three full bathrooms, a spacious living/dining area, in-unit laundry, and a covered lanai with built-in Viking BBQ. Interiors feature high-end appliances, granite countertops, travertine floors, and optional private elevators for multi-generational convenience.
Rental Listings
Map View
Very Best Deluxe Ocean View...Panoramic View....First Class!!From $806/night · Sleeps 8
Maui Breeze Retreat at Ho'olei openings Jul 19-29, Aug 22-Sep...From $1,266/night · Sleeps 8
Hoolei Uni 31-2 Ocean view- ideal Wailea location walking to...From $1,300/night · Sleeps 8
Summer Deal Wailea Villa with Ocean Views and Private LanaisFrom $959/night · Sleeps 8
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'oleiFrom $925/night · Sleeps 8
Ocean View Villa, Heart of Wailea, Ho'olei L1 23-1, Third...From $999/night · Sleeps 8
Luxury Villa Steps from Wailea Beach with Resort Amenities &...From $1,357/night · Sleeps 8
Luxury Villa with Artful Decor, Stunning Views, Gourmet Kitchen &...From $912/night · Sleeps 8
Summer Deal Ocean View Wailea Villa with Pool and Resort...From $996/night · Sleeps 8
Luxurious Ho'olei Villa with Ocean Views, Two Story Townhouse!From $1,382/night · Sleeps 6
Panoramic Views - Fourth Row Ho'olei - One of a...From $1,099/night · Sleeps 8
Ho'olei Ocean View 21-6 Newly Listed, Renovation May 2025From $999/night · Sleeps 8
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand,...From $1,149/night · Sleeps 8
Summer Deal Beachfront Wailea Villa with Pool Hot Tub and...From $853/night · Sleeps 6
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8...From $920/night · Sleeps 10
SUMMER SALE! Luxurious 3BR Villa Sleeps 8 - Hoolei Residences...From $791/night · Sleeps 8
From $806/night
My wife and I are proud to offer the very best Deluxe Ocean View villa in all of Ho'olei for your vacation. Only the top row buildings (A-F) are...
From $1,266/night
Surround yourself with the lush scenery of Maui Breeze Retreat at Ho'ol!ei, a tastefully decorated two-story villa with spectacular views of the...
From $1,300/night
Dramatic ocean views, this spacious town home is approximately 2500 sq ft of interior footage and 596 sq ft of lanai space. The Hoolei community is...
From $959/night
This property is hotel zoned, and not being affected by the recent proposed legislation.Located in highly desirable secluded area of neighborhood...
From $925/night
Come relax and enjoy your stay at our spectacular ocean-view luxury villa, located directly across from the Grand Wailea Hotel & Spa on the beautiful...
From $999/night
Located on the third tier on the south side of the Ho’olei Resort on Maui, our two-level villa has jaw-dropping Pacific Ocean views and is perfectly...
From $1,357/night
This property is hotel zoned, and not being affected by the recent proposed legislation.Wailea Beach, voted one of the top beaches in the world, is a...
From $912/night
This property is hotel zoned, and not being affected by the recent proposed legislation.Breathtaking Views and Picturesque Sunsets!!! Ho'olei 39-3...
From $996/night
Ho'olei Villa 17-1 is a beautifully remodeled 3-bedroom, 3.5-bath townhome offering stunning ocean views and breathtaking sunsets. Located in...
From $1,382/night
This Ho'olei ocean view villa is a luxurious two-story townhouse in Wailea, offering sweeping ocean views and elegant island living. This spacious...
From $1,099/night
Newly Remodeled in 2023! Come relax and enjoy the spectacular ocean and island views in this rare three bedroom condo perched on the very top row...
From $999/night
Remodel completed in 2025!Ho’olei’s largest floor plan. Spacious 4,305 sqft, 3 bedroom 3.5 bath (sleeps 8) Ocean and tropical views without a sea of...
From $1,149/night
One of a kind four bedroom Ho'olei home in Wailea!Breathtaking is the best word to describe this luxury townhouse-style villa at Ho’olei, situated in...
From $853/night
This property is hotel zoned, and not being affected by the recent proposed legislation.The Best Villa Experience at Ho'olei in Maui awaits you at...
From $920/night
Indulge in a tropical retreat at Ho'olei 12-2 in Wailea, Maui! This opulent 3-bedroom, 3.5-bathroom vacation rental, showcasing the Maile floor plan...
From $791/night
FLASH SUMMER SALE!!! We're offering exclusive discounts on all summer stays booked this week—don't miss out on these updated lower rates.Stunning...
Hoolei has large three-bedroom villas in a gated hillside community, with garages, lanais and resort-style amenities instead of a standard condo-village layout.
Rentals are usually three-bedroom villas, often with three-and-a-half bathrooms, full kitchens, laundry rooms, private lanais and garage parking.
No. Hoolei is across from the Grand Wailea area and near Wailea Beach, but visitors should check the exact walking route and any resort-access rules for the rental.
Yes. Hoolei has a pool area with sandy beach entry, waterfalls, hot tubs and a children's pool area, along with fitness and gathering spaces.
Some rental programs include Grand Wailea access, while others may not. Visitors should confirm resort privileges on the exact villa page before booking.