Summer Deal Wailea Oceanfront Villa with Pool Hot Tub and Sunsets

Top rated by guests
Welcome to your Maui sunset sanctuary
Sophisticated half bath perfect for guests
Plush linens and soft tones create a restful retreat
Unwind in comfort with easy outdoor access
Every detail designed for comfort and quiet elegance
review stars
10Outstanding
(51 Ratings)
"Everything was even better than expected. We were impressed by the way the kitchen was stocked with every utensil needed and all the supplies provided. It was clean and very comfortable for our family..."
Patrick Y.
Don't miss out! Price and availability may change
10 / 10
Outstanding(51 Ratings)

House in Wailea

8 guests · 3 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

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

Amenities at Summer Deal Wailea Oceanfront Villa with Pool Hot Tub and Sunsets

Non-smoking
No pets allowed
Family friendly

Map of Wailea

city location on map

Ratings and reviews

10 / 10
Outstanding(51 Ratings)
10 / 10Outstanding·Jul 2026
Everything was even better than expected. We were impressed by the way the kitchen was stocked with every utensil needed and all the supplies provided. It was clean and very comfortable for our family of 8. One minor glitch was that I was notified the unit was ready for us to check in but when we arrived about 45 minutes later, we were met by someone from the office who said she had to do a "security check" before we were allowed to enter, so we had to wait about 30 minutes before we could go in. We did not mind enjoying the Maui sun for a half hour. The only comment was that there were no beaters found for the hand mixer in the kitchen. If that's the only "complaint" from a group of 8, I would say you're doing very well with your preparations! We thoroughly enjoyed the accommodations and would stay there again. Pricey but not excessive for what you get and besides, one must expect to pay for Paradise!
10 / 10Outstanding·Jul 2026
Amazing property. Very clean. We will be back.
10 / 10Outstanding·Jun 2026
Amazing view from the balcony. Loved grilling out there for our family while watching the sunset. Very spacious unit for our family of 5. And an even closer walk to the beach than we had anticipated. Highly recommended!
10 / 10Outstanding·Jun 2026
We spent 4 nights at the property and everything was great. The unit itself was clean, had everything needed for a comfortable stay and was very well appointed. The view was absolutely amazing, the property had great pools & amenities and the communication with the property management was excellent. We loved the unit and would book it again without hesitation. Highly recommend.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Summer Deal Wailea Oceanfront Villa with Pool Hot Tub and Sunsets. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Summer Deal Wailea Oceanfront Villa with Pool Hot Tub and Sunsets pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Summer Deal Wailea Oceanfront Villa with Pool Hot Tub and Sunsets?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.