Ho‘olei Villas was named the best resort in the Hawaiian Islands with a score of 98.86 for 2019. A record 600,000 dedicated Condé Nast Traveler readers cast votes for over 10,000 hotels and resorts to identify the best travel experiences in the world. Condé Nast Traveler Readers’ Choice Awards are the longest-running and most prestigious recognition of excellence in the travel industry.

CLOSEST VILLA TO THE POOL. Breathtaking is the best word to describe this luxury townhouse-style villa at Ho’olei, situated in beautiful Wailea on the sunny, southwestern shore of Maui. Ho’olei is the ultimate dream home in paradise!

Our home is the largest floor model, the Hibiscus (3,301 square-feet), allowing space for an indoor dining area, as well as a 686 square-foot lanai for entertaining or relaxing outdoors. Our home has a semi-private and secure backyard just adding more space to satisfy all of your family needs. Four private bedrooms, all with king beds and bathrooms (ensuites), as well as a powder bath give the home a feeling of personal space. The home has vaulted ceilings, custom Italian cabinetry and upgraded appliances in the kitchen, deep soaking tubs in the master bath, and a secure, one-car attached garage with another detached covered parking for a secondary car.

Our homes are not affiliated with the Grand Wailea pools. Ho’olei has a less crowded, 5-star pool with a baby beach, nineteen foot waterfall, swim-in-grotto, two whirlpools, men’s and women’s sauna and beautiful locker rooms with showers, all surrounded by a plush environment.

We greet your family at the unit and give you a tour of the beautiful pool with waterfalls, Jacuzzi, sand beach side and exercise room. We explain all the functions of this state-of-the-art home and answer any questions you might have regarding the Ho’olei experience and the island of Maui.

Our Island Team will welcome you to your villa, and answer any of your questions and make sure you have everything you need for your vacation. Upon your arrival, we will have a tray of local products for you to sample and enjoy. Other amenities that we offer that others may not, include a stocked kitchen with items chosen by you before you arrived, additional cleaning or babysitting.

Located across from the Four Season's Resort, the Grand Wailea and the Wailea Beach Villas, Ho'olei, Maui, you are within walking distance of some of the most popular resort beaches on Maui.

Ho'olei is in the town of Wailea and nestled in between the Four Seasons Resort and the Grand Wailea Resort. The shops at Wailea are within walking distance. One of the most beautiful beaches in the world is just across the street. The spa at the Grand Wailea is also voted to be one of the best Spas in the world year after year. There are some great restaurants with high marks on Zagat. There is also a wonderful beach path that is perfect for an early morning job or an evening stroll.

Included with the rental of this Villa: Gated-electronically controlled entry and on-site security.


  • Satellite or cable
  • No Smoking
  • Washer & Dryer
  • TV
  • Children Welcome
  • Internet
  • Air Conditioning
  • Parking
  • Accessible
  • Hot Tub
  • Swimming pool
  • Heater


  • Television - All Bedrooms Have Flat Screen TV's
  • Cable TV
  • Books
  • Toys - Boogie Boards and Beach/Pool Toys

Location Type

  • Downtown - Great shopping at The Shops at Wailea which is within walking distance from our Villa.
  • Resort - Situated in the center of the Wailea Resort
  • Golf Course View - The world class golf courses are all around you. Enjoy the Emerald, Green or Blue courses.
  • Mountain View - The West Maui Mountains are set up right behind the Wailea Resort. They are something special in the early morning.
  • Ocean View - The Ho'olei Resort sits across from the world famous Grand Wailea and exquisite Four Seasons Resort. Ho'loei offers ocean views.

Safety features

  • Smoke detector
  • Carbon-monoxide detector


  • We provide beach chairs and towels, umbrella, boogie boards, rolling cooler, picnic basket and beach and pool toys.


  • Telephone
  • Air Conditioning
  • Heating
  • Linens Provided
  • Washing Machine - Laundry room in the home.
  • Clothes Dryer
  • Parking - Second designated car spot close by.
  • Garage - Personal one car attached garage and a second, designated car port close by.
  • Internet
  • Towels Provided - Home, Beach and Fitness Towels.
  • Safe
  • Fitness Room / Equipment
  • Wireless Internet - FREE Internet for your stay.
  • Iron & Board
  • Hair Dryer
  • Paper Towels
  • Shampoo
  • Basic Soaps
  • Elevator - Personal, interior elevator in home
  • Living Room


  • Lawn / Garden - Semi-private backyard
  • Balcony
  • Beach Chairs
  • Beach Towels
  • Porch / Veranda
  • Deck / Patio - Private Lanai
  • Outdoor Furniture
  • Tennis - You can enjoy tennis for a minimal fee at the Wailea Tennis Center.
  • Golf


  • wheelchair accessible - This property is well suited who need a little extra assistance in getting around.

Onsite Services

  • Massage
  • Private Chef
  • Housekeeper Optional


  • Dishwasher
  • Refrigerator
  • Stove
  • Oven
  • Microwave
  • Grill
  • Coffee Maker - We provide both, a Keurig and Drip for your convenience.
  • Toaster
  • Ice Maker
  • Dishes & Utensils
  • Kitchen - Beautifully stocked kitchen with upgraded appliances.


  • Upstairs Master Bedroom Suite #1 (King bed) with bathroom and walk-in shower.
  • Downstairs Bedroom Suite #2 (King bed) with bathroom and walk-in shower/tub.
  • Downstairs Bedroom Suite #3 (King bed) with bathroom, walk-in shower and jacuzzi tub.
  • Downstairs Bedroom Suite #4 (King bed) with bathroom, walk-in shower and jacuzzi tub.
  • Upstairs half bath off main living area.


  • Indoor seating for 5 at Kitchen counter
  • Indoor seating for 6 at Dining table
  • Outdoor seating for 6 at lanai table

Pool / Spa

  • Sauna - In the pool area.
  • Heated Pool
  • Communal Pool - Waterfalls, sandy beach entrance, plush environment.
  • Hot Tub - Located at the Ho'olei Pool


  • Booking Possible