Book Direct with Owner and Save!
  • Ho’olei Kitchen
  • Ho’olei Master Bathroom
  • Ho’olei Master Bedroom
  • Ho’olei Ocean View
  • Ho’olei Wailea Pool
Relaxing pool with waterfalls and child friendly areas.
Walking distance to breathtaking beaches.
Beach side bars, pool bars, lagoon side bars.
Golf Course
World renowned Wailea Golf Course is next door.
Snorkel trips, fishing trips, whale watching.
Fine and local dining within minutes.

Vacationers at the Hoolei community enjoy some of the finest amenities available anywhere. Entry to the gated community is electronically controlled and features on-site security 24/7. The property management office is conveniently located on site. Shuttle service is available among residences and to the recreation center, the Grand Wailea Resort Hotel & Spa and beach. There are plenty of recreational opportunities for vacationers at the Ho'olei community. The luxurious tropical pool features a sandy beach entry and beautiful 19-inch waterfall. There's even a paid option to enjoy a poolside massage. A children's pool and two jacuzzi spas on site. The fully-equipped fitness center features cardio and weight-training machines, locker rooms, showers, and men's and women's saunas. Read More

Ho’olei Luxury Vacation Rentals

Located in the Wailea area behind The Grand Wailea hotel, Hoolei is a world-renowned luxury community that is the ideal destination for your dream vacation. The Hoolei Wailea rentals are luxurious two-story town homes conveniently situated above the Hoolei Grand Wailea Resort Hotel & Spa and Four Seasons Resort Maui. The town of Kihei with local favorite beaches and eateries is minutes away.

What makes the Ho’olei community so appealing? First, the climate is nearly perfect all year around. In addition, besides overlooking the vast Pacific Ocean; the West Maui Mountains, the islands of Lanai and Kaho’olawe and the Molokini crater are easily within view. The carefully-planned layout and landscaping of the Ho’olei luxury Rentals community help to make these stunning views possible. To top it off, the amenities, people and homes are remarkable!

NO Guest Booking Fees
Save Money and Time
Book Directly with Owner
Best Ho’olei Home Location

Growing fees, out of date calendars, bait and switch and fraud issues with sites like and are discouraging guests and owners. In smaller, luxury locations like Ho’olei, owners and guests are losing interest in large booking sites, because of the lack of attention and quality. Owners like us prefer to communicate and book directly with their guests. Guests prefer to receive accurate, timely information for a smooth and easy booking process. Working directly with the owner ensures better communication, save money, time and cuts the headache out of booking. Our photos and descriptions are recent and accurate. There are NO guest Booking Fees. Guests communicate directly with the owner and the process is seamless and easy.

Home Floor Plan

ho-olei-master-bedroomOur unit provides 3 Bedrooms, 3.5 Bathrooms and sleeps 8 to 10 people. The home is 3,464 squar feet. Our Maile floor plan is the only plan that features a bedroom large enough upstairs to accommodate two queen size beds. Our home feature a large great room with vaulted ceilings; central air conditioning; three full baths plus a powder room; a laundry room with washer, dryer and stainless steel utility sink; and large storage closet. The floor in each room features either stone or luxurious carpeting. Our kitchen is furnished with custom Italian cabinetry, granite counter tops, two refrigerators with freezer drawers and icemaker, a 30-inch gas cooktop, a 30-inch built-in microwave, a dishwasher and a kitchen island. Each master bedroom suite of our Hoolei rental features a large walk-in closet with safe, dual vanities with custom Italian cabinetry, a soaking tub, a shower and a private lavatory. Bedrooms two and three each contain a spacious closet and en suite bath with custom Italian cabinetry. Bedroom three is privately located on the upper floor. The attractive exterior of every Hoo’lei town home features stucco with natural stone finish, double-hung low-e glass windows, concrete roof tiles and copper rain gutters. Each home has a lanai and some have ocean views. There’s an attached one-car garage plus a covered carport. Lastly, the location is one of the best. Directly looking down to the pool, you have easy and quick access to the most desired amenities in the community. See Maile Floorplan

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