Villa vacation rentals in Wailea

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Top-rated villa rentals in Wailea

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An open living area with large glass doors showcases a scenic view of the sea and landscape. A kitchen island with a sink features a stylish countertop. Comfortable seating arrangements are placed throughout, enhancing the casual ambiance of the space.
Villa in Lahaina
5 out of 5 average rating, 9 reviews

One of Our Best, Highly Rated ~ Paradise for 2

Aloha! Welcome to Hale 'Ikena Makai, pronounced Ha-lay e-ken-na ma-ki, 'Home with a View of the Sea'. This property is the original member of Platinum Maui Vacations. We include: ~Resort Shuttle ~Secured wifi / internet ~Central AC (new 2020) ~Quality Cal King bed with Clean & Fresh linens over hypoallergenic covers ~Tommy Bahama beach chairs ~Big fluffy beach towels ~Ice cooler ~Boogie boards ~24/7 on call, on island contact ~Dedicated & covered parking NO DISAPPOINTMENTS HERE ~ Always 5 Stars

Guest favorite
The living area features comfortable seating with a sofa and armchair. A wooden coffee table is centered in front of the sofa. Natural light enters through large glass doors that lead to an outdoor patio, creating an inviting space for relaxation.
Villa in Lahaina
4.93 out of 5 average rating, 44 reviews

Ground floor, ocean view, private, Kapalua Ridge

Welcome to Kapalua Ridge Villa 612. This large 1 bedroom, 2 bathroom 1125 sq ft condo features an open floor plan with a large private shaded lanai. Admire Honolulu Bay, sunsets, whale watching, sailboats, & more. This condo has ocean views from the lanai, living area, dining area, & kitchen. The unit can comfortably accommodate 4 people. The pool is a few steps away & there is a walk path that leads you all the way down to the resorts/beach. Kapalua Ridge Villas is coastal Luxury at it's best.

Top guest favorite
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, 16 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 favorite
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, 97 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 favorite
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, 328 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.

Villa in Lahaina
New place to stay

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 favorite
An outdoor lanai features a spacious dining table surrounded by multiple chairs, with stunning panoramic ocean views visible beyond the railing. Bright blue skies and a few clouds enhance the setting, complemented by nearby tropical greenery.
Villa in Lahaina
4.85 out of 5 average rating, 91 reviews

Panoramic Ocean-View Villa steps from the beach!

Enjoy amazing, panoramic views in this bright and open island living area connected to an expansive lanai balcony. Great for families with a connected living and entertaining space, but also quiet and private with two bedrooms that each have their very own private patios and dual vanity bathrooms. This is a very flexible space that is ready for the vacation that you want to make of it! Kapalua has world-class beaches, beautiful landscapes, and amazing activities/amenities all around!

Guest favorite
The living area features a mix of seating options, including a light-colored sofa and a dark leather recliner. A large television is mounted on the wall, with natural light streaming through expansive windows. Lush greenery can be seen outside, enhancing the room's connection to nature.
Villa in Lahaina
4.97 out of 5 average rating, 38 reviews

Our Kapalua Golf Villa piece of paradise, Specials

Enjoy our condo in the spectacular Kapalua area. Nestled on the 4th fairway of the beautiful Kapalua Bay Course, has unobstructed views of the golf course with ocean views in the background. The peaceful setting is perfect for any getaway without the madness of the hotel scene. The condo has all kitchen amenities, full size washer / dryer, king size bed in master, 2 bathrooms, pull out couch in living room, WiFi, cable tv and no stairs! Come enjoy our piece of paradise!

Guest favorite
Villa in Lahaina
4.86 out of 5 average rating, 44 reviews

Special! Ocean/Golf Course Views Kapalua 2BD/3BA

We welcome and thank you for your support of Maui. Beautiful spacious ocean view, 2 bdrm/3 ba Villa. Lanai, new sofabed, platform bed, flooring, 2 Pools, BBQ area, wifi, free parking, new washer/dryer. Photos do not do it justice. Views across the Kapalua Golf course is the Ritz Carlton gives you an idea of this exclusive neighborhood. Popular for returning guests which speaks volumes. Feel free to ask questions. Professional Cleaners

Superhost
The image captures a serene view of the beachfront condominium complex surrounded by lush landscaping. Palm trees provide shade near the outdoor pool area, while the ocean's blue waters are visible in the background. The buildings exhibit a modern architectural style against a clear sky.
Villa in Lahaina
5 out of 5 average rating, 7 reviews

Sands Of Kahana MAUI 1, 2 & 3 BR Some View units

The Sands of Kahana is located on the world famous West Coast of Maui between Kaanapali and Kapalua. The Sands of Kahana is a deluxe beachfront condominium property located on Kahana Beach, midway between the world famous Kaanapali and Kapalua resorts. Spacious two & three bedroom villas. Tennis, pools, spa, restaurant, bar, beach activities center, barbecues and more. Ten minutes to five championship golf courses.

Guest favorite
A scenic view of the oceanfront resort features a large, winding pool surrounded by palm trees and tropical foliage. Loungers are arranged along the poolside, with gentle waves visible in the background. The sky is clear, and the atmosphere reflects a relaxing beachfront environment.
Villa in Lahaina
5 out of 5 average rating, 15 reviews

Kaanapali beach KBC, 1 bdrm on ocean, scenic view

beautiful oceanfront resort features one-bedroom Villa Suites directly on world famous Kaanapali Beach! Relax in the king size bed. Living room features Queen sofa bed with Tempur-Pedic mattress. Each unit has a private Lanai. This unit is scenic view. This resort is 5 miles north of where the Lahaina fires took place and was not at all affected. Tax ID TA-056-945-7152-01R

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, 93 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.

Popular amenities for Wailea villa rentals

When is the best time to visit Wailea?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ8,630ﺩ.ﺇ9,181ﺩ.ﺇ8,924ﺩ.ﺇ9,526ﺩ.ﺇ6,996ﺩ.ﺇ9,556ﺩ.ﺇ7,760ﺩ.ﺇ7,760ﺩ.ﺇ6,787ﺩ.ﺇ5,527ﺩ.ﺇ7,947ﺩ.ﺇ6,875
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Quick stats about villa rentals in Wailea

  • Total vacation rentals

    Explore 40 vacation rentals in Wailea

  • Nightly prices starting at

    Wailea vacation rentals start at ﺩ.ﺇ1,102 per night before taxes and fees

  • Verified guest reviews

    Over 610 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Wailea vacation 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!

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