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Wailea · South Maui

Hoolei

Hoolei is a gated hillside community of large multi-level villas across the street from Wailea Beach, with a lush shared pool that rarely feels crowded. It suits multigenerational families and groups who want ensuite bedrooms, big lanais for sunset dinners and a walk to the sand.

What guests say

1 in 3 reviews mention kids or family

Guests love

  • Uncrowded resort-style pool. The lush complex pool, with a hot tub and a gym nearby, feels like a resort pool without the crowds, and kids and teens use it daily.
  • Built for big family groups. Three- and four-bedroom villas with ensuite baths let several generations share one roof and still have their own space.
  • Lanai life up the hill. Guests spend much of their time on big lanais with grills, watching sunsets and, in season, whales from the villas higher on the slope.
  • Beach via the Grand Wailea. Wailea Beach is across the street through the Grand Wailea grounds, and teens can walk on their own to the Shops at Wailea.

Worth knowing

  • Road noise on some lanais. Villas backing onto the main road hear steady traffic outdoors; several guests said it took away from lanai time, while others barely noticed.
  • A hill to climb. Upper villas trade views for a steep walk down to the pool and beach and back up; some guests drive and park, and beach wagons help.
  • Stairs, and elevators vary. Villas are multi-level with stairs, and only some have elevators, so confirm if anyone needs one.
  • No Grand Wailea perks. A few guests note that staying here does not include use of the Grand Wailea pools or facilities, though day passes may be an option.
Choosing a unit: Villas in the lower buildings near the entrance and pool (the 12 and 24 buildings) are the easiest walk to the pool and beach but are mostly garden-view and closer to road noise; for ocean and sunset views, guests point to villas higher up the hill.

This review summary is AI-assisted, drawn from 338 recent guest reviews (Nov 2024 to Aug 2026) of the rentals we list. Units are individually owned, so details vary. Read the latest reviews

At a glance

Unit types
3 and 4 bedrooms, sleeping 6 to 10
Air conditioning
All 32 rentals we list
Pool
Yes
Ocean views
6 of the 32 rentals we list. We check every view claim.
Nearest beach
Wailea Beach, 0.4 mi
Airport
About 30 minutes from Kahului Airport (OGG)
Size
About 30.1 acres, 120 units
Address
146 Hoolei Cir, Wailea, HI 96753
Map of Hoolei and the nearest beaches Open in Google Maps
  1. 1Wailea BeachBeach · 0.4 mi
  2. 2Polo BeachBeach · 0.5 mi
  3. 3Ulua and Mokapu BeachBeach · 0.8 mi
  4. 4Palauea BeachBeach · 0.8 mi
  5. 5Keawakapu BeachBeach · 1.2 mi
  6. 6Poolenalena BeachBeach · 1.4 mi

Straight-line distances from the building.

Rentals at Hoolei

Our top-rated rentals here, from the 32 we list.

Ho'olei Ocean View VillaOcean viewHo'olei Ocean View Villa3 bd · 4 ba · sleeps 10$1,918 avg/night 5.0 (175)Ho'olei 52-4Ho'olei 52-43 bd · 4 ba · sleeps 8$1,545 avg/night 5.0 (160)Maui Breeze Retreat at Ho'oleiOcean viewMaui Breeze Retreat at Ho'olei3 bd · 4 ba · sleeps 8$1,926 avg/night 5.0 (152)Hoolei Uni 31-2 Ocean view- ideal Wailea locationHoolei Uni 31-2 Ocean view- ideal Wailea location3 bd · 4 ba · sleeps 8$1,616 avg/night 5.0 (87)Ho'olei Villa 12-1, S1Ho'olei Villa 12-1, S14 bd · 4 ba · sleeps 8$1,585 avg/night 4.9 (114)Hoolei 17-3Hoolei 17-33 bd · 4 ba · sleeps 8$1,529 avg/night 5.0 (79)

See all 32 rentals and check dates

Nightly prices by bedroom

BedroomsRentalsAverage per nightRange
330$1,566$1,319 to $2,083
42$1,637$1,585 to $1,689

The typical nightly price of each rental we list, with Hawaii's 18% tax and the cleaning and booking fees included, as of November 2026. Holiday dates cost more.

Recent guest reviews

Hoolei Uni 31-2 Ocean view- ideal Wailea location
★★★★★ August 2026

Property was everything and more- great location, very well appointed with a fantastic ocean view. We had a toddler with us and it was super nice that the property provided a Graco and high chair. It also had a great inventory of beach supplies. The community pool and gym were also really nice. We had a couple minor glitches with the air co and bbq but the management team was SO responsive and addressed them very quickly. We had an amazing time and can’t wait to come back!

Anne F.
Ho'olei Ocean View Villa
★★★★★ August 2026

Great place for a larger group with kids. Beach access was easy and the views are unforgettable. Close to shops and restaurants. Kids had a great time at the pool during evening hours while parents relaxed on the balcony. Would definitely stay here again.

Nikita P.
Hoolei 39-2
★★★★★ August 2026

Very comfortable for our three families.Everyone enjoyed the extra items for going to the beach and pool area.The location was very good for the general pool and for a short walk to the beach.Our host gave very good directions for how to get to the beach and the check in went smoothly.The extra parking space was just across the street under a large carport.The only issue I had was the outdoor coach was so deep which made this furniture hard to use.Over all this was an excellent rental unit.

Kevin G.
Ho'olei 12-4
★★★★★ July 2026

All was great- except the floors were dirty. Under our feet and socks were always dirty walking in the unit

Celeste F.
Ho'olei Villa 12-1, S1
★★★★★ July 2026

This place was amazing and the host was extremely responsive as I was trying to decide what resort to stay at. Even though it is not ocean or pool views the views out the windows are beautiful with all the Hawaiian landscape/foliage that is so beautiful. When this place lists that it is the closest unit to the pool and beach it is a true statement. The pool is basically a few steps away from the unit and beach is across the street and through the Grand Wailea resort which is absolutely beautiful and a fun place to walk through. I would love to have been able to use the facilities there but you have to book through them to use them. I believe you can buy day passes which I would strongly consider if we came back because it is amazing. The pool here is beautiful too and offers perfect size and layout for both kids and adults and was never crowded at all, we never struggled to find lounge chairs. Again, the unit itself is stunning, the decor and detail is over the top. The outdoor kitchen was perfect and had everything we needed. We did a fishing trip through Green Island Charters and scored dinner for a couple nights and had everything we needed to grill and serve a great meal. They even had some of the basics like salt/pepper, wide variety of spices, plastic wrap, and plenty of paper products, dishwasher detergent, laundry detergent, nice, branded hand soap, shampoo and conditioner etc.... I would strongly recommend this place! Thank you, Derek Stattin!!!!!

Rita G.
Hoolei 21-6
★★★★★ July 2026

The villa is lovely. Starting to show its age in some ways. Good location, especially if you have a car. Walking to the beach is challenging.

Robert C.
Ho'olei 21-3
★★★★★ July 2026

Fantastic experience! Everything as advertised and described!

Steven J.
Ho'olei 93-2
★★★★★ July 2026

Great property and condo. Our family enjoyed all the amenities. Would definetly reccomend and stay again.

Wayne M.

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