Summer Deal Wailea Oceanfront Villa with Pool Hot Tub and Sunsets

Kihei, Hawaii
$1280 avg/night
Bed 3

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

This property is hotel zoned, and not being affected by the recent proposed legislation.

Breathtaking Views and Picturesque Sunsets!!! Ho'olei 39-3 offers spacious, upscale living in a private gated community. Escape and relax at this opulent two-story Villa.

As you enter 39-3, be in awe at the impressive art pieces tastefully placed throughout the villa. Be drawn into the gloriously decorated great room and flow seamlessly out to the lanai via the grand push back, floor-to-ceiling sliding doors.

Your private patio is complete with large dining table, chaise loungers and outdoor kitchen with Wolf gas grill and Sub Zero mini fridge. Enjoy the ultimate indoor/outdoor experience and be mesmerized by views of the Pacific. While dining al fresco on the lanai or if enjoying meals at the stately formal dining table, it is hard to miss the captivating Maui sunsets.

The gourmet kitchen is equipped with state-of-the-art brands and every utensil a chef could dream of to prepare a five-star meal. Beautiful cabinetry, stone counters and large breakfast bar with additional seating for six PLUS views of the ocean complete this spectacular kitchen.

Each of the 3 luxurious bedrooms has its own en suite bathroom. The guest room, located on the main level, has two queen beds with sleeping for up to four and has a TV and DVD player.
The two Primary suites are located on the lower level along with the laundry room with full sized washer and dryer. Both suites offer king size beds with plush linens and share the lower level ocean view lanai that is perfect for morning coffee.
The larger Primary suite offers a peaceful spa-like sanctuary with huge soaking tub, separate large stone shower and massive dual vanity. A perfectly serene atmosphere to recharge after a day of adventuring.

Heavenly is the best word to describe the 2nd Primary. With the drapes drawn and sliders open, the room is bright and airy and full of natural light and ocean breezes. The plush four poster canopy bed drapes you in flowy fabrics and has enough pillows to make you feel like you are sleeping in a cloud.

Ho’olei is just moments from Wailea beach, voted one of the top beaches in the world. This amazing beach has numerous activities such as paddle boarding, snorkeling, sea kayaking, swimming, boogie boarding and relaxing on the beautiful shore. During the winter months, Humpback whales can be easily seen from Wailea beach. There is a breathtaking oceanside walking/running trail that spans 1.8 miles one way.

There is ample seating along with a fitness center. Located just moments from dining and shopping at 3 resorts as well as The Shops at Wailea. You may dine at any of the resort restaurants as well as set up spa appointments, but please note that hotel pool access at the adjacent resorts is not included with your reservation. Ho’olei offers a stunning large resort-style pool complete with water falls, a sandy artificial beach for kids and 2 hot tubs. Also provided is 24 hour on-site security and gated access.

While we strive to keep all photos up to date, there may be new and updated pieces of furniture or décor that are different than in the original pictures. The functionality, available seating and sleeping space will remain the same or may improve.Other things to notePlease note: Upon confirming your reservation, we will request your personal email address. A company specific rental agreement will be emailed to the provided address. Once we have received your completed rental agreement, detailed arrival instructions will be emailed to you one week prior to your stay.Registration number210081190063, TA-041-265-9712-02

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Gated Community Unit Size: 2700 Sq Ft (251 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator (mini) Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Recommended Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi, With Speed Of 100+ Mbps (good For 1–2 People Or Up To 6 Devices)
  • OUTDOORS

    Balcony Fenced Yard Gas Grill
  • POOL/SPA

    Heated Pool Hot Tub Massages Shared/communal Pool
  • BATHROOMS

    3.5 Bathrooms Bathtub Hair Dryer Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Ecotours Nearby Fitness Center Fitness Facilities Nearby Golfing On Site Hiking/biking Trails Nearby Mountain Biking Nearby Snorkeling Nearby Surfing/body Boarding Nearby Swimming Nearby Tennis On Site Windsurfing Nearby Winery Tours Nearby
  • ENTERTAINMENT

    DVD Player Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • FAMILY FRIENDLY

    Playground
  • LOCATION HIGHLIGHTS

    Near A Hospital Near The Bay Near The Sea
  • SERVICES AND CONVENIENCES

    Housekeeping (on Request) Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Elevator Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Rates & Availability

Review Review

  • Marcus F.

    Submitted Dec 8, 2025

    Stayed Nov 23, 2025

    The home is nicely appointed with all the kitchen tools you need.

  • Arol A.

    Submitted Jun 16, 2025

    Stayed Jun 10, 2025

    Top notch place to stay! Great location even better view!

  • Heather B.

    Submitted Apr 6, 2025

    Stayed Mar 28, 2025

    We loved the location and access to the beach. Great to be able to stop in at the pool after the beach on the way up the hill. Views from the terrace were fabulous and we loved the whale watching. Kitchen nicely organized and stocked for all of our needs.

  • Maneesh S.

    Submitted Feb 24, 2025

    Stayed Feb 15, 2025

    We stayed at this beautiful home for just under a week. My family (wife, 3 children ages 2 - 4, and I) and my brother's family (brother, his wife, and 2 children ages 7-9) were all very comfortable. CB Islands was extremely responsive and the location and view could not be beat. We will be back again!

  • Jim S.

    Submitted Jan 12, 2025

    Stayed Dec 26, 2024

    We love this property enough that this is the second time we rented it. We highly recommend it.

  • Brian H.

    Submitted Oct 15, 2024

    Stayed Oct 10, 2024

    This was one of the best stays we've ever had! This was perfectly appointed wirh every annenity. The views were beautiful. The property was perfectly maintained. We are so grateful to have had such a luxurious experience!

  • Connie R.

    Submitted Sep 10, 2024

    Stayed Sep 3, 2024

    My husband and I took our kids to Hawaii 20 years ago and thought we do it again with their significant others who had never been. We all had a fantastic time making memories of cooking together in the huge kitchen, adventures and family game night and sunsets. We would definitely return here.

  • Leo Z.

    Submitted Jan 20, 2024

    Stayed Dec 14, 2023

    I rented this place for a month for my family and we were not disappointed. Really one of the best places to stay in Ho'olei. The view from the Lanai is incredible and the place comes with 8 beach chairs, 2 umbrellas, and plenty of beach towels great for going to any beach. The pool area in the community is great with a gym and two big jacuzzis and waterfalls. The only thing I would improve is the downstairs bedroom's bathroom's water pressure and shower. The water pressure is too weak and the shower is awkward in my opinion. If the unit is available when I come back for my next trip I will be booking it again.

  • Julie S.

    Submitted Jul 7, 2023

    Stayed Jul 1, 2023

    Gorgeous villa, beautifully decorated and appointed. View is magnificent, and access to Grand Wailea for beach is very convenient. Property manager was attentive and pleasant throughout our stay. Highly recommend - we’ll be back!

  • Mike W.

    Submitted Jun 20, 2023

    Stayed Dec 31, 1969

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This was our 2nd Airbnb of the Trip. We had amazing views overlooking the ocean and the Four Seasons hotel. It was a short walk to the beach and we had access to the restaurants and bars at the Four Seasons as well!

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Total

Includes taxes and fees
$1,280+
View details