Vacation rentals in Wailea Beach

4.98 out of 5 average rating, 223 reviews

A group of alpacas, varying in color and patterns, stands along a fence in a lush green pasture. Their calm expressions reflect the peaceful environment, with rolling hills and trees visible in the background, creating a serene rural setting.

Guesthouse in Kula

Upcountry Alpaca, Llama, and Rabbit working farm

Experience Maui's first working fiber farm, home to Alpacas, Llamas, and Angora rabbits. Sitting at 3300 ft above sea level, Cottontail Farm enjoys perfect weather days and crisp, cool nights. The cooler temperatures are perfect for our wool producing animals that graze just outside your cottage in the back yard. Our alpacas and llamas are quiet observers but also provide plenty of entertainment of their own. Our group of Angora rabbits can be seen out the window hopping around their enclosures.

A bright living area offers ocean views through expansive sliding glass doors. Comfortable chairs are positioned towards the balcony, where coastal scenery includes palm trees swaying in the breeze. Neutral decor is accented with beach-themed cushions, and a TV set is present on a stylish console.

4.99 out of 5 average rating, 192 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on Keawakapu beach! Mana Kai is a hotel zoned resort in an ideal location, right on the border of Wailea and Kihei! Our condo is designed with a modern surf feel in mind, we are excited to share it with you! If you enjoy Wailea's 5-star resorts but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach, stay with us! We have the best Property Mgr. in Maui, Tracy O'Reilly to take amazing care of you!.

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.

4.95 out of 5 average rating, 209 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.

4.99 out of 5 average rating, 116 reviews

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

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.

4.96 out of 5 average rating, 139 reviews

A modern kitchen and dining area are visible, featuring a round table set for four with woven placemats and plates. Stainless steel appliances are arranged in the sleek kitchen design, while large sliding glass doors open to reveal views of lush gardens and the ocean beyond.

Condo in Wailea

A.R.A Retreats: Big Blue Pacific

Nicknamed “Big Blue Pacific” for its absolutely stunning view of the Pacific Ocean from the living room, kitchen and master bedroom. Our vacation rental condo is located in Wailea Ekolu, the well-known luxury resort community of Wailea. It offers a relaxing 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 and when the sun goes down, watch your favorite shows on on our smart tvs!

4.95 out of 5 average rating, 132 reviews

A serene landscape view features tropical greenery and palm trees leading to the ocean. Sun umbrellas are visible along the shore, providing shade, while calm blue waters stretch into the distance. Lush foliage surrounds the area, enhancing the tranquil outdoor environment.

Apartment in Kihei

Wailea Couples Retreat, 300 FT To Keawakapu Beach

Ekahi Ocean Studio is perfectly located in the lower village of Wailea Ekahi (ground floor), a lush-landscaped paradise, just steps from the oceanfront pool and to world-renowned Keawakapu beach. This studio is perfect for couples seeking a peaceful, romantic retreat. You can spend your days lounging at the beach or oceanfront pool, running along the nearby beachfront pathway, exploring nearby Wailea restaurants and resorts or enjoying our cook's kitchen and your private Lanai.

The spacious living area features vaulted ceilings with exposed beams and large glass doors that open to stunning ocean views. Comfortable seating includes two patterned armchairs and a cozy sofa. A coffee table is centered in the room, and the dining area is illuminated by pendant lights.

4.96 out of 5 average rating, 107 reviews

Upscale and Elegant Vistas

Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled in September of 2021, no expense was spared to create our ocean view oasis. This one-bedroom, two-bathroom condo features thoughtful luxurious finishes throughout. Located in sunny and luxurious Wailea, with all of Maui is within reach. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy a day at the beach nearby.

The spacious living area features a comfortable seating arrangement with a large flat-screen TV. Bright light enters through multiple windows, enhancing the airy ambiance. The dining space displays a round table set for four, surrounded by elegant chairs, and views of the lush outdoor landscape.

4.87 out of 5 average rating, 134 reviews

*Last Minute Deal*Luxurious*2b/2b OceanView Wailea

This ground floor 1071 square foot unit is situated just above the 11th fairway of the Wailea Blue Course. The living room and master bedroom have private lanais that step out to a relaxing open lawn with sweeping ocean views. Features include AC throughout the property, bamboo floors throughout, brand new tile in the master bathroom, granite counter tops, and cherry cabinets. Tastefully decorated this spacious condo truly has everything you will need!

4.96 out of 5 average rating, 437 reviews

A welcoming living area features a comfortable sectional sofa beside a modern coffee table, with natural light filtering through large windows. An outdoor patio is visible, with an umbrella-shaded table and chairs overlooking lush tropical gardens and ocean views.

Home in Kihei

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

4.98 out of 5 average rating, 129 reviews

The living area is arranged with comfortable seating over a textured carpet. A low coffee table holds decorative elements, while art adorns the wall and a modern kitchen with stainless steel appliances is visible in the background, enhancing the open layout.

Condo in Wailea-Makena

130K Hawaiian Reno on Wailea Blue Golf *Ocean View

BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of WaileaCheck out our other property #201 VRBO (2050379)+#1905 VRBO(1222713) in The Palms we are Super Host with 5 STAR reviews)!! BOOK UP TO 365 DAYS.

Superhost

A spacious lanai features comfortable seating arrangements, including a table and chairs for outdoor dining. The ocean and lush landscape provide a scenic backdrop, visible through the open railing. The ceiling displays exposed beams, enhancing the open and airy feeling of the space.

4.86 out of 5 average rating, 111 reviews

Wailea Ekolu - Gorgeous Ocean View - AC, Smart TV!

E Komo Mai to our luxury 2 bedroom unit on the 2nd floor with a beautiful ocean view and a spacious interior. From our comfortable lanai seating you have a full 180 degree view of the islands of Molokini, Kahoolawe, Lanai, and the West Maui Mountains while enjoying your morning coffee, evening cocktail, or anytime meal. Enjoy the luxurious grounds, pristine pool and scenic nearby beach walk.

The image captures a sunset view over the ocean, with vibrant colors reflecting off the water. Silhouetted palm trees line the beach, and footprints are visible in the soft sand, creating a tranquil and inviting coastal scene.