Villa holiday rentals in Wailea

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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 resort landscape is depicted, featuring a lagoon-style pool surrounded by palm trees and lounge areas. Ocean waves gently lap at the shore in the background, with a clear blue sky above. The building architecture showcases multiple levels, blending naturally with the tropical environment.
Villa in Lahaina
5 out of 5 average rating, 17 reviews

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6

2 Bedroom Westin Nanea Ocean Villa at Kaanapali Beach on Maui Island in Hawaii; 1,260 SQ FT; SLEEPS UP TO 6 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; Pool. Renter can check-in late or check-out early anytime during reservation period without penalty but no refunds or credits will be provided. Actual villa unit is assigned at check-in and views will vary; Free self-parking

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, 100 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!

Superhost
Villa in Lahaina
5 out of 5 average rating, 5 reviews

Westin Kaanapali Resort North Ocean-View Studio

OCEANVIEW STUDIO @ Westin Kaanapali Ocean Resort Villas NORTH on Kaanapali Beach; 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. Renter can check-in late or check-out early anytime during reservation period without penalty but no refunds or credits will be provided. Actual unit is assigned at check-in & OCEANVIEWS will vary; Free self-parking

Top 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, 358 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.

The outdoor area features palm trees swaying against a colorful sky, overlooking a lawn with lounge chairs and thatched umbrellas. The distant ocean is visible beyond the lush greenery, enhancing the calm atmosphere of the resort's grounds.
Villa in Lahaina

Westin Ka’anapali Ocean Resort Villas, beach front

Westin Nanea, north or south Ocean Resort Villas, 2 bedroom (sleeps 6) Bring the whole family to this beautiful beach front property with lots of room for fun or get away for a romantic vacation. This is a timeshare and dates are flexible depending on availability at the time of booking. Includes multiple on site restaurants, 2 pools, water slides, store, poolside service, rentals, beach views, convenient free shuttle to downtown Lahaina. Sports bar, live music & more! Use of all resorts.

Villa in Lahaina

Westin Nanea Kaanapali Luxury Ocean Villa Sleeps 6

Westin Nanea Ocean Villa @ Kaanapali Beach, Maui. Spacious living and dining areas, full kitchens, washer/dryers, & remarkable resort views. This 2 Bedroom 2 Bath sleeps 6 w/free parking. **Available Only June 28th, 2026 - July 5th, 2026.- 7 Night Stay.** Eat at one of the on premise restaurants, lounge by a rejuvenating pool, surf several nearby breaks, enjoy a spa, or work out in the Fitness Studio. When the sun sets behind the palms of Kaanapali, sink into your Westin Heavenly® Bed.

Guest favourite
The image captures a spacious pool area surrounded by lush tropical landscaping. Lounge chairs are arranged neatly around the large swimming pool, which glimmers under the clear blue sky. A multi-story resort building stands in the background, providing a glimpse of the beach and ocean.
Villa in Lahaina
4.91 out of 5 average rating, 87 reviews

Kaanapali Beach Club "Scenic View"

**PLEASE ASK! We have many more weeks, dates and many GUARANTEED views!** Prices based on views, events, etc. **HOTEL TAX of approx 19.00 per night paid to resort upon check in.** Located on Maui's world famous Ka'anapali Beach. Vibrant tropical landscaping, first-rate amenities and exclusive array of leisure activities. Kaanapali Beach Club offers a one-acre swimming pool with separate kids pool, as well as calming outdoor whirlpool hot tubs. *Stock Photos

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 Lahaina
4.81 out of 5 average rating, 102 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, 68 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 Lahaina

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.

Villa in Lahaina

Maui Westin Kaanapali 1Bdrm Villa in Paradise

Westin Kaanapali sits on the beach. This studio sleeps 4 has a full kitchen, dining, and washer and dryer. This resort has it all. Gym, spa, pools and spas for adults and children, restaurants, bars, and equipment rentals. Close to Lahaina and golf courses you don't need to go far to have it all.

A spacious pool area is visible, bordered by lush tropical gardens and palm trees. The ocean is seen in the background, with sun loungers arranged around the pool. A rocky feature adds visual interest, enhancing the serene ambiance by the water.
Villa in Lahaina
5 out of 5 average rating, 4 reviews

1 Bdrm Condo on Bch, KBC in Ka'anapali beach

Beautiful ocean front resort features 1 bedroom villa suites directly on world famous Ka'anapali Beach! Relax in the king size bed. Living room features queen sofa bed with Tempurpedic mattress. Each unit has a private Lanai! Tax ID TA-056-945-7152-01R

Popular amenities for villa rentals in Wailea

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Avg. price£1,743£1,854£1,803£1,924£1,413£1,930£1,567£1,567£1,371£1,390£1,331£1,380
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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 £260 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 & child-friendly amenities

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    50 of Wailea holiday rentals include wifi 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!

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