Vacation rentals in Wailea Beach

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Top-rated vacation rentals in Wailea Beach

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Guest favorite
A refreshing swimming pool with a unique shape is set against a backdrop of vibrant green landscaping and palm trees. The pool area features a hot tub and is surrounded by well-maintained gardens. In the distance, ocean views are visible under a bright blue sky.
Condo in Kihei
4.88 out of 5 average rating, 147 reviews

100KContemporaryHawaiian Reno in Wailea-Beach/Golf

Stunning 100K Recent Reno+New Decor for a Hawaiian Beach Vibe. Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa. World Class Golf+Shopping. Ground flr condo with private wrap around lanai. King Master Bed with a contemporary private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel or take long tropical beach walks.BOOK UP TO 365 DAYS

Guest favorite
A clear blue pool is surrounded by palm trees, creating a relaxing atmosphere. Lounge chairs are positioned along the deck, offering spots for sunbathing. Umbrellas provide shade for outdoor dining tables nearby, all with a scenic view of the ocean in the background.
Condo in Kihei
4.95 out of 5 average rating, 216 reviews

Maui's Best - Wailea Ekahi 47A

Ekahi says it all. Don't come all the way to Maui to stay in a bargain space. Unit 47A is a one bedroom (with sleeper sofa), two-bath renovated on the ground floor. This means a larger lanai than upper units. It also means that when you step off that lanai, you step onto A LOT of grass. Our condo is a 5-minute (barefoot) walk to the most wonderful of all Maui beaches; a ten-minute walk to the shops at Wailea. Restaurants nearby. Convenient yet without the road noise.2067153903 Privacy and peace.

Top guest favorite
An open dining area features a round table made of natural wood, surrounded by woven chairs. A well-equipped kitchen with stainless steel appliances and quartz countertops is visible in the background. Large sliding glass doors provide unobstructed views of the ocean and nearby palm trees.
Condo in Wailea-Makena
4.94 out of 5 average rating, 305 reviews

A.R.A Retreats: The Molokini

FULLY Renovated Summer 2023! Nicknamed “Molokini” this condo has stunning ocean view front and center of Molokini, you can witness multiple humpbacks jumping and playing during whale season from the comfort of your own private lanai. This condo is located in Wailea Ekolu in the well-known luxury resort community of Wailea. It offers a beautiful space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views

Top guest favorite
Condo in Kihei
4.99 out of 5 average rating, 125 reviews

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Wailea Ekahi is a luxurious resort fronting onto beautiful Keawakapu Beach with acres of tropical grounds and 4 pools. Unit 16B is a mid property, renovated ground floor ocean view studio unit (500 sq feet) with a King sized bed, walk in shower and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens while enjoying ocean views. A short walk to the beach, pools, luxury shopping, highend dining and golf courses.

Top guest favorite
A stunning beach scene captures vibrant sunset colors reflecting off wet sand. Rocky outcrops frame the tranquil waters, while palm trees sway gently in the foreground. Wispy clouds stretch across the sky, adding depth to the evening landscape.
Condo in Kihei
4.99 out of 5 average rating, 180 reviews

Romantic, Luxury Retreat w/Ocean View-Couples Only

Luxury 1 bedroom 2 bath condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. If our condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525 Not suitable for children or infants.

Top guest favorite
An expansive covered lanai features comfortable seating with plush cushions, accented by a decorative table. String lights adorn the ceiling, and panoramic ocean views showcase a vibrant sunset over palm trees and neighboring properties.
Guest suite in Kihei
4.99 out of 5 average rating, 127 reviews

Sweeping Panoramic Ocean Views - Private Ohana

Live like a local at the Ocean Blue Ohana - the private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500 feet above sea level, looking at the most glorious views of the neighboring islands, mountains, coastline, and Maui's amazing skyline. To top it off, you are 5 minutes from the Wailea Resorts and beautiful golden sand, crystal clear beaches.

Top guest favorite
A modern kitchen is shown with sleek gray cabinetry and stainless steel appliances. An island seating area with two wooden stools is present, topped with a decorative tray and two cups. Pendant lights with blue shades illuminate the space, enhancing the open and functional layout.
Condo in Kihei
4.96 out of 5 average rating, 189 reviews

Renovated Condo | 3 Min Walk to Toes in the Sand!

Welcome to Pacific Pearl — your serene Maui escape just steps from golden-sand Kamaole Beach Park II. Set in the lush, resort-style Maui Banyan complex, this fully remodeled ground-floor condo offers peaceful garden views, a walkable location near dining and shops, and all the comforts of home. Spend your mornings snorkeling, your afternoons lounging by the pool, and your evenings with sunset walks on the shore. Perfect for couples, families, or friends seeking the effortless Maui getaway.

Top guest favorite
A light-filled living room features a designer sectional sofa and a wooden coffee table. Floor-to-ceiling glass doors offer unobstructed views of the ocean and balcony. A modern TV is positioned on a wooden console, enhancing the contemporary aesthetic of the space.
Condo in Kihei
4.99 out of 5 average rating, 243 reviews

Luxury condo • 180° Ocean Views • Steps to Beach

Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

Guest favorite
A spacious living area is characterized by wood-paneled walls and natural light from large sliding glass doors. A comfortable queen-sized sleeper sofa and two accent chairs are arranged around a coffee table. A flat-screen smart television is mounted on the wall, adorned with complementary artwork.
Condo in Kihei
4.9 out of 5 average rating, 103 reviews

Luxury Condo in Wailea Ekahi w/Direct Beach Access

Do you want direct and private access to probably the best beach (i.e. Keawakapu) on Maui? Then look no further than our unit in the Wailea Ekahi complex! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. You are also in walking distance to the stores and restaurants at the Shops at Wailea and also the Wailea Beach Path. This condo has everything you need to make your Maui experience memorable, luxurious, and convenient.

Top guest favorite
Home in Kihei
4.96 out of 5 average rating, 448 reviews

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

Top guest favorite
A modern dining area features a polished wooden table surrounded by six chairs. Natural light floods the space, highlighting the contemporary kitchen with granite countertops in the background. Large sliding glass doors open to a scenic view of the ocean and lush surroundings.
Condo in Wailea
4.94 out of 5 average rating, 186 reviews

Wailea Ekolu Village 2/2 with stunning ocean view!

Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this Wailea Resort condo has received government approval to operate as a vacation rental for the next 5 years.

Guest favorite
An inviting pool area is surrounded by lush tropical landscaping. The clear blue water of the pool is complemented by several lounge chairs and tables with umbrellas, providing shaded seating. A serene atmosphere is created by the vibrant greenery in the background.
Condo in Wailea-Makena
4.91 out of 5 average rating, 119 reviews

Grand Champions - King Bed - Close to Wailea Beach

We are located in the heart of Wailea at the Grand Champions Villas, close to Maui's best beaches and within walking distance to great restaurants, the Shops of Wailea and surrounded by Championship Golf Courses. Grand Champions is a serene 12-acre park-like resort next to the Wailea Tennis Club and Wailea Blue Golf Course. Have fun with the whole family at this stylish place.

Popular amenities for Wailea Beach vacation rentals

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