Villa holiday rentals in Wailea

Find and book unique villas on Airbnb

Top-rated villa rentals in Wailea

Guests agree: These villas are highly rated for location, cleanliness and more.

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Guest favourite
A coastal view features tall palm trees swaying gently against a clear blue sky. The sandy beach stretches along the shoreline, leading to calm turquoise waters. In the distance, a glimpse of a distant landmass is visible, adding to the serene atmosphere.
Villa in Wailea
4.96 out of 5 average rating, 101 reviews

Luxury at it's Finest, Truly a Home away from Home

Remodeled in 2020, this 2 /2 Villa is located at Grand Champion Golf & Tennis Villas in the exclusive resort destination of Wailea, Maui. We have been named a Super Hosts on Airbnb due to the great amenities, comfort, safety, cleanliness and luxurious accommodations this Villa provides. Wailea is the Gold Coast of Maui, close to pristine beaches, shopping and dining and this is a legal, exclusive vacation rental. Spacious and luxurious, feel Refreshed and Anew in your Home away from Home!

Guest favourite
A private rear deck features a shaded area with tropical foliage and bamboo fencing. Two surfboards and beach gear are neatly stored, along with a round table and colorful chairs for seating. A large black container sits in the corner, adding to the functional outdoor space.
Villa in Kihei
4.92 out of 5 average rating, 367 reviews

Steps from Beach • Park at YOUR Private Back Door

Ground-floor, bottom corner unit across from Cove Beach — close to beach sunset, surf, food trucks and local stores. The only unit with a tandem parking stall right next to your wall and back deck entrance. Step out of your car, walk straight in to your smart lock security door on your own back deck. Fully upgraded with fast Wi-Fi, two AC units, new appliances and a lava rock shower with hot/strong pressure. Sleeps 4 with a master + studio, beach gear, well-stocked kitchen and fresh linens.

Superhost
A serene beach scene features a sand shoreline dotted with tropical trees and umbrellas. In the foreground, a group is seen kayaking on clear blue waters, while a resort building rises in the background, surrounded by lush greenery.
Villa in Kaanapali

Westin Kaanapali Beach Resort IslandView 1BR Villa

Submit your requested dates & I will check availability & respond if I can confirm this owner rental. 1 BR Premium Islandview Villa Westin Kaanapali Ocean Resort; 900 SQ FT; SLEEPS 4 ADULTS Resort is located on beautiful Kaanapali Beach. All the luxuries & amenities of a Westin resort + comfort of a villa w/ furnished kitchen, in-room washer/dryer, private balcony. Resort activities; gym/spa; Pools. Actual unit is assigned at check-in & views will vary; Free self-parking & no resort fees

Superhost
An aerial view of the resort showcases multiple low-rise buildings surrounded by lush greenery and palm trees, adjacent to a sandy beach and turquoise ocean. The scenic landscape includes rolling hills in the background, providing a serene atmosphere.
Villa in Kaanapali

Westin Kaanapali Ocean Resort Villas North Studio

Submit your requested dates & I will check availability & respond if I can confirm this rental for you. STUDIO Villa @ Westin Kaanapali Ocean Resort Villas NORTH on Maui Island Hawaii; 480SQ FT; SLEEPS UP TO 4 ADULTS All the luxuries & amenities of a Westin resort +comfort of a villa w/ furnished kitchenette, in-room washer/dryer, private balcony. Resort activities; gym/spa; Pool. Actual villa unit is assigned at check-in and views will vary (most likely Island View); Free self-parking

Superhost
An aerial view captures the expansive Westin Kaanapali Ocean Resort Villas, nestled along a golden sandy beach. Lush green lawns and palm trees frame the property, which features multiple buildings harmoniously integrated with the coastline and surrounding landscape.
Villa in Kaanapali

Westin Kaanapali Resort North 1BR IslandView Villa

1BR Premium Island-View Villa @ Westin Kaanapali Ocean Resort Villas NORTH on Maui; 750 SQ FT; SLEEPS 4 ADULTS All the luxuries & amenities of a Westin resort +comfort of a villa w/ furnished kitchen, in-room washer/dryer, private balcony. Resort activities; gym/spa; Pools. Renter can check-in late or check-out early during reservation period without penalty but no refunds or credits will be provided. Actual villa unit is assigned at check-in; Island Views will vary; Free self-parking

A spacious outdoor area features a private pool with clear blue water, framed by stone landscaping. An arched structure offers shade near the pool, and a red bowl sculpture adds a pop of color. Lush greenery surrounds the space, enhancing the serene environment.
Villa in Kaanapali
4.8 out of 5 average rating, 104 reviews

Kaanapali Fairway Villa 3BR, 3BA.

Welcome to this Kaanapali Golf course 3 bedroom 3 bath bed and breakfast. Permit number BBWMT 2021/0003-159 Halelo. This beautiful Mediterranean home is conveniently located on hole number 5 of the Kaanapali Golf Course with a private pool, swim up bar, and ocean view. Recently renovated with many added amenities and features, please see in description below.

Guest favourite
The open kitchen and living area features a large island with seating and modern appliances. A casual sofa is positioned across from the kitchen, and natural light streams through a window framed in dark wood. A patterned area rug adds texture to the space.
Villa in Kihei
4.96 out of 5 average rating, 70 reviews

Kihei Villa: Pool, Near Ocean & Garden Views

Kick back and relax in this calm, stylish space. This Villa features 2 king suites, peek-a-boo ocean views, and private lanais off of each bedroom. The main living area comprises a great room with vaulted ceilings and a large island in the kitchen. Custom cabinetry houses all the essentials needed for cooking and relaxing while at the Villa.

Two sparkling pools are surrounded by lush tropical landscaping, featuring palm trees and vibrant plants. A hot tub is positioned near a rocky feature, and lounge chairs are arranged around the main pool area, inviting relaxation in a tranquil outdoor space.
Private room in Kaanapali

The Westin Ka'anapali Ocean Resort Villas 1 BR

My place is close to family-friendly activities, great views, restaurants and dining, the beach, and nightlife. You’ll love my place because of the outdoors space, the neighborhood, the comfy bed, the light, and the kitchen. My place is good for couples, solo adventurers, business travelers, families (with kids), and big groups.

Guest favourite
A modern living area features a flat-screen television mounted on the wall. A wooden sideboard offers decorative accents, while a cozy dining nook with a live-edge wooden table provides seating. Large windows allow natural light to illuminate the space, with glimpses of tropical greenery outside.
Villa in Kihei
4.95 out of 5 average rating, 116 reviews

Walk to Cove Beach Park from a Refined Villa

Prep meals in a chic kitchen with granite surfaces and white-washed hardwood floors. Dine at a live-edge table in a cozy corner nook amid nautical décor and modern touches. Unwind in a lounge chair on a sun-drenched patio before taking a swim.

Villa in Kaanapali
4.46 out of 5 average rating, 13 reviews

Spectacular 3/3 Ocean view Villa with AC, pool

Nestled on the hillside of Ka’anapali, this top-of-the-line quality 3-bedroom/3-bath villa offers panoramic views of the islands of Lanai and Molokai. Every inch of this villa is BRAND NEW!

Popular amenities for Wailea villa rentals

When is the best time to visit Wailea?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$3,353 AUD$3,567 AUD$3,467 AUD$3,701 AUD$2,718 AUD$3,712 AUD$3,014 AUD$3,014 AUD$2,636 AUD$2,673 AUD$2,561 AUD$2,653 AUD
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Quick stats about villa rentals in Wailea

  • Total holiday rentals

    Explore 50 holiday rentals in Wailea

  • Nightly prices starting at

    Wailea holiday rentals start at $499 AUD per night before taxes and fees

  • Verified guest reviews

    Over 670 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Wailea holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wailea rentals

  • 5 Average rating

    Wailea stays are highly rated by guests—averaging 5 out of 5!

Destinations to explore

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  4. Maui County
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