Villa vacation rentals in Wailea

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Top-rated villa rentals in Wailea

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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
The kitchen and dining area feature modern appliances and a large wooden table surrounded by a built-in bench. Natural light enters through the window, illuminating the granite countertops and stylish cabinetry, while a beach-themed artwork complements the tropical surroundings.
Villa in Kihei
4.89 out of 5 average rating, 116 reviews

Chic Villa 2 | Modern Vibes by the Ocean

Experience an older Hawaiian style charm with a modern twist in this newly remodeled Villa in Kihei. Welcome to 1 Bedroom, 1 Bathroom Villa 2 at Villas by the Cove — a laid-back, beach-chic retreat just across the street from Cove Park and a short 3-minute stroll to Charley Young Beach. This modern villa features a living room with air conditioning, high-speed Wi-Fi, a fully equipped kitchen, a comfortable king bed, a full bathroom with a walk-in shower, a private lanai, and gated parking.

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, 333 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.

Guest favorite
A modern kitchen space features navy blue cabinetry contrasted with light countertops. Stainless steel appliances are included, along with a black faucet above the sink. A serene wall art piece and access to a well-lit living area are visible in the background.
Villa in Kihei
4.83 out of 5 average rating, 47 reviews

Newly renovated 2BR/2BA with Bonus Family Room

Complete renovation October 2024! This unit is a two bedroom, three bath with downstairs family room condominium villa with direct access to shared pool. Each bedroom, living room, and downstairs family room has its own AC unit for temperature control. Guests may choose from a King bed or two twin beds in the bedrooms, with two queen beds located in the family room. The beach is less than a 2 minute walk! Note: Hawaii GET, TA & MCTAT taxes of 17.962% are included in total price shown.

Guest favorite
A modern living area features a light hardwood floor and a cozy sectional sofa. A large flat-screen TV is mounted on the wall, while a decorative plant adds a touch of greenery. The open concept layout leads to a spacious kitchen with navy blue cabinets.
Villa in Kihei
4.89 out of 5 average rating, 37 reviews

Newly Remodeled Beach Hideaway, Sleeps up to 8!

Lele Hideaway is a two bedroom, three bath with an additional downstairs family room condominium suite with direct access to the shared pool area. Each bedroom, living room, and family room has its own air conditioning unit for complete temperature control. The bedrooms have a full ensuite bathrooms and are located on the ground floor. The beach is less than a two minute walk! Note: Hawaii GET, TA & MCTAT taxes of 17.962% are included in total price, no additional taxes charged.

Superhost
A large, inviting pool is surrounded by lush greenery and palm trees, featuring waterfalls and rocky landscaping. Various seating areas with umbrellas can be seen, along with a bridge spanning a small waterway, all leading towards the ocean in the background.
Villa in Lahaina
4.5 out of 5 average rating, 6 reviews

Marriott Maui Ocean Club 1BR 2BA

Marriott’s Maui Ocean Club is one of the most popular timeshare resorts - and for good reason! Kids and kids-at-heart will get a kick out of the resort's 3.5- acre super pool complete with a water slide, waterfalls, and children's area. The poolside bar is a great place to rest and relax while the little ones splash until their heart's content. Maui Ocean Club also offers amenities such as a beauty shop, barbecue area, game room, and restaurants.

Guest favorite
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, 67 reviews

Modern 2 bedroom/2bath Villa near Beach!

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 is comprised of 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. Dual king bed suites feature full baths with enclosed walk in showers and silent A/C units.

Guest favorite
A modern living area features a gray sofa facing a sleek coffee table on a patterned rug. Large sliding glass doors reveal an outdoor dining space and view of palm trees and the ocean, enhancing the connection to the tropical surroundings.
Villa in Kihei
4.92 out of 5 average rating, 88 reviews

Ocean View Villa at Villas by the Cove!

Enjoy a refreshing dip in the pool before kicking back on a premium white sandy beach. This stylish villa features a modern slate décor, state-of-the-art kitchen, private covered lanai, and tropical garden of mango and palm trees. The condo is part of an upscale property tucked away on a residential oceanfront side street. Surf schools, bicycle rentals, spa treatments, and farmer’s market are just around the corner.

Guest favorite
A modern living area is featured with neutral-toned furnishings, including a large sofa and a wooden accent chair. A flat-screen television is mounted on a light wood panel. Natural light fills the space through windows, with a contemporary coffee table set in front.
Villa in Kihei
4.89 out of 5 average rating, 35 reviews

Newly Remodeled 2 Bed/2 Bath - Close to Beach

Ohana Hale is newly remodeled two bedroom, two bathroom ground floor condominium suite on a shared property. Each bedroom has air conditioning, in addition to one full bathroom and its own private entrance to the shared pool. Guests can choose between a King bed or 2 Twin beds. Note: Hawaii GET, TA & MCTAT taxes of 17.962% are included in total price, no additional taxes charged.

Guest favorite
An aerial view captures the beach front cottage alongside a sandy beach and crystal-clear waters. Lush greenery surrounds the property, with palm trees lining the shore. Small figures may be seen enjoying the beach, adding a sense of activity to the serene landscape.
Villa in Kihei
4.88 out of 5 average rating, 16 reviews

Ocean Front Cottage, 30 steps to the beach!

BEACH FRONT!! Stunning views from this charming beach front cottage located in the heart of Kihei town! This 850 square foot one bedroom, two bath home fronts a sandy beach and offers gorgeous sunset views. Conveniently all one level, this home is ideal for families of four or couples. Beach Front Honu Cottage offers the perfect paradise getaway, with a million dollar view!

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, 95 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 favorite
A modern kitchen area features sleek dark cabinetry and a spacious island with three high-backed stools. Natural light fills the open space, highlighting a living area with a cozy chair, a decorative table, and a surfboard mounted on the wall.
Villa in Kihei
4.92 out of 5 average rating, 90 reviews

Ocean View 2BR Villa Steps To The Beach

Villa 4 is a 2 Bedroom, 2 Bathroom remodeled Villa with a spacious living room and ocean view patio. This Villa offers privacy and comfort set back in a tropical lush garden filled with mango and palm trees. This single story, stand-alone villa that is charming, convenient, and clean. Note: Hawaii GET, TA & MCTAT taxes of 17.962% are included in our prices.

Popular amenities for Wailea villa rentals

When is the best time to visit Wailea?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price€ 2,040€ 2,170€ 2,109€ 2,252€ 1,654€ 2,259€ 1,834€ 1,834€ 1,604€ 1,306€ 1,879€ 1,625
Avg. temp16°C16°C16°C17°C18°C18°C19°C20°C19°C19°C18°C17°C

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 € 260 per night before taxes and fees

  • Verified guest reviews

    Over 620 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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