From $878/night
Very Best Deluxe Ocean View...Panoramic View....First Class!!
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...
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Hoolei Luxury Villas
Stay at Hoolei for luxury Wailea villas near resort amenities, beaches, pools, golf, dining, and Maui activities.
Hoolei Vacation Rentals offer luxury villa-style stays in the Hoolei area of Maui. The property is a useful option for travelers who want condo-style comfort near Wailea beaches, golf, resort dining, Kihei, Makena, and South Maui roads. As a result, guests can enjoy a practical island base with access to beaches, dining, scenic drives, and Maui activities.
In many listings, Hoolei rentals may include one-bedroom, two-bedroom, or larger layouts with kitchens or kitchenettes, private lanais, Wi-Fi, parking, laundry access, air conditioning or ceiling fans, and garden, resort, partial ocean, or ocean views. However, each unit can vary by owner and booking source. Therefore, guests should compare exact amenities, views, fees, bedding, cooling options, and policies before booking.
Hoolei works well for travelers who want a comfortable Wailea rental with more flexibility than a standard hotel room. In addition, the property location can make it easier to enjoy nearby beaches, restaurants, shopping, and tours. For many visitors, the main appeal is the mix of space, convenience, and Maui scenery.
Wailea and Makena shoreline conditions can change with swell, wind, and season. Therefore, guests should check posted signs, lifeguard guidance, surf reports, and current conditions before entering the ocean.
Nearby roads connect guests with beaches, scenic drives, dining areas, and tour departure points. In addition, activity choices should match the region, season, and current ocean conditions.
Before booking, compare the exact location, view, floor level, kitchen setup, Wi-Fi, parking, laundry access, cooling options, pool access, beach distance, and final fees. Also, confirm quiet hours, cancellation terms, resort fees, and shared amenity rules before reserving.
If Hoolei rentals are limited for your dates, compare Wailea vacation rentals, Kihei vacation rentals, Makena vacation rentals, or Maui luxury vacation rentals. You can also browse all Maui vacation rentals for more islandwide options.
Hoolei Vacation Rentals offer a flexible way to enjoy Maui with more space, practical amenities, and access to nearby beaches and activities. Select rentals may include lanais, kitchens, pools, ocean views, or resort-style features. Overall, this page is a helpful starting point for comparing stays that match your travel style and location preferences.
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Very Best Deluxe Ocean View...Panoramic View....First Class!!From $878/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 $1,400/night · Sleeps 8
Exquisite Oceanview Villa with Resort Amenities in Gated CommunityFrom $964/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 $858/night · Sleeps 8
Luxury Villa with Artful Decor, Stunning Views, Gourmet Kitchen &...From $912/night · Sleeps 8
Ho'olei Villa 17-1: Luxury Retreat with Breathtaking Ocean ViewsFrom $1,000/night · Sleeps 8
Luxurious Ho'olei Villa with Ocean Views, Two Story Townhouse!From $1,705/night · Sleeps 6
Panoramic Views - Fourth Row Ho'olei - One of a...From $1,185/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 $1,829/night · Sleeps 8
Designer Villa Luxurious 3BR/3.5BA, Private Elevator, Resort Pool, Beach Access!From $858/night · Sleeps 6
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8...From $1,102/night · Sleeps 10
SUMMER SALE! Luxurious 3BR Villa Sleeps 8 - Hoolei Residences...From $791/night · Sleeps 8
From $878/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 $1,400/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 $964/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
This villa at Ho'olei was renovated in 2024. The renovations are extensive. New extra large kitchen island with ocean view seating: all new...
From $858/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 $1,000/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 $1,705/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 $1,185/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 June 2025! See the new photos just posted!The entire home has been repainted, almost all the furniture was replaced, a lot of new...
From $1,829/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 $858/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 $1,102/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.Ho'olei 93-3...