Holiday houses in Wailea

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Wailea

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top Guest favourite
Guest suite in Pepeekeo
4.94 out of 5 average rating, 372 reviews

Garden Suite at Onomea

A lovely, private and very clean cottage with all amenities for a comfortable and peaceful stay. Quiet, and cool the year around, we are a 20 minute walk from the Hawaii Tropical Botanical Garden and well situated for touring to Waipio Valley, Akaka Falls, Volcano National Park, and many other destinations in the area. Come see the real Hawaii.... lush, tropical, friendly and far less touristy than the Kona side. We would love to have you come and stay! Please take a look at our reviews.

Guest favourite
A private tile lanai offers a shaded seating area with a wooden railing, opening to views of a lush yard and tropical greenery. The space is designed for relaxation, with ample room for enjoying the surrounding nature.
Guest suite in Papaikou
4.85 out of 5 average rating, 204 reviews

Hale Hamakua studio apt., 5 min. to downtown Hilo!

Close to many major attractions yet short drive to downtown Hilo. You’ll love the comfortable space, the peaceful yet convenient location, the lush yard, even access to swimming & waterfalls in the gorge behind the house. The studio is good for couples, solo adventurers, and business travelers. NOTE: Hawaii GE-067-950-7968-02 & TA-067-950-7968-01 The rental is hosted & per Hawaii County Planning Dept exempt from Hawaii Cty Bill 108 so we may consider <30 day rentals as well as longer periods.

Top Guest favourite
The open living space features a comfortable seating area with light-toned furniture. Large sliding doors reveal an ocean view, leading to a sunlit deck. A wooden dining table with chairs is visible alongside a media console, balanced by tropical artwork adorning the walls.
Home in Hakalau
5 out of 5 average rating, 58 reviews

Oceanfront "Treehouse" at Hakalau with Kitchen

Welcome to our Treehouse at Hakalau! The only way to stay closer to the ocean would be in a boat. Watch the cruise ships slowly pass by knowing that the passengers aboard are truly envying your accommodations. This quaint and unassuming second story home offers 180 degree views of the mighty Pacific ocean! Relax and watch seasonal whales as they breach the blue water, spinner dolphins chase a passing fishing vessel, and the rising sun as it welcomes you to an amazing array of morning colors.

Guest favourite
A comfortable guest studio is featured, furnished with a queen bed dressed in soft linens. A small table and chair sit beside a window, providing natural light. A mini-fridge and microwave are also visible in the room, which is surrounded by lush greenery seen through the windows.
Guest suite in Hakalau
4.94 out of 5 average rating, 209 reviews

Private Studio short walk to Hakalau Beach Hamakua

Private/separate from the main house guest studio in lovely Hakalau village. NEWLY RENOVATED for more square footage & A/C. Easy access and parking, comfortable queen bed, private bath, spacious shower, HD Smart TV, cable, high speed WiFi and kitchenette. Lush landscaping and private bistro garden. A short walk from the house is a spectacular rainforest hike down to the shoreline. Surfing, ziplining, waterfalls, hiking, biking, horseback riding and more within a short drive from the house.

Top Guest favourite
Farm stay in Hakalau
4.95 out of 5 average rating, 425 reviews

Forest Hale Cabin @ Permaculture Farm, Waterfall

A beautiful get-away surrounded by nature on a cacao farm! One-bedroom + loft cabin, full kitchen, bathroom, w/d, sunny lanai, on our Big Island off-grid permaculture farm. Cabin is nestled in a food forest a few hundred feet from a stunning waterfall with swimming hole in a peaceful bamboo grove. One king-size bed in bedroom, two twin beds in loft, which has low ceiling & is accessed by steep narrow stairs. Free entrance to botanic garden. Organic eggs, homemade chocolate at farmstand!

Top Guest favourite
A spacious lanai is depicted, featuring wooden railings and a hammock. Lush green lawns and tropical plants are visible in the surrounding area, with Hilo Bay and a blue sky in the backdrop, creating a serene outdoor environment.
Condo in Hilo
4.99 out of 5 average rating, 253 reviews

Hilo Bay Sunrise

Location! This great new solar home is located just 2 miles north of downtown Hilo while sitting on quiet acreage in a gated community overlooking the Hilo Bay and Coconut Island, 5 miles to the airport. The perfect balance of being in the country and close to everything! Very close to black sand beaches, surf, botanical gardens and waterfalls! Hilo Farmer’s Market, and Volcano National Park. Relax in the hammock on the lanai with tropical breezes! Please note there are entry stairs.

Top Guest favourite
A tranquil pool area is framed by palm trees and tropical plants, with a stunning ocean view in the background. A decorative pillow featuring the name 'Hale Laule'a' rests on the pool's edge, inviting relaxation and enjoyment of the serene surroundings.
Guesthouse in Hakalau
4.96 out of 5 average rating, 263 reviews

Oceanfront Estate Retreat 1 - Carriage w/ Horses

Experience unmatched luxury in a one-bedroom apartment of a world class, $10+M gated oceanfront estate perched on a dramatic cliff edge with a pool. Wake up to breathtaking sunrises, panoramic ocean views in your spacious apartment that features a private lanai, separate living and sleeping rooms, full kitchen, bathroom with walk-in rainfall shower, bidet, and custom furnishings. This property offers privacy, elegance, and stunning surroundings for singles, couples, or honeymooners.

Top Guest favourite
Home in Pepeekeo
4.95 out of 5 average rating, 112 reviews

Sugar Mill Ranch House with Amazing Ocean Views

Come stay in this serene Hawaiian ranch house with breath-taking ocean views. Just outside of Hilo, this 2-bedroom, 2-bath sits peacefully on a hillside next to an old Sugar Mill. Private and modern, this home is a short driving distance from Akaka Falls, the charming town of Honomu, Honolii Beach Park, and the Hawaii Tropical bioreserve and gardens. This ranch house is outfitted with a full kitchen, high speed internet, a wrap-around porch, and plenty of organic fruit trees.

Top Guest favourite
The exterior of the Mango Tree Cottage is surrounded by lush greenery, featuring tropical plants and vibrant flowers. A covered porch leads to the entrance, while the cottage is nestled amidst a serene natural setting, inviting a connection with the outdoors.
Guesthouse in Hakalau
4.97 out of 5 average rating, 67 reviews

Mango Tree Cottage : Nestled in the Forest

PEACEFUL, CALM & VIBRANT! A Sacred Space nestled under an ancient mango tree. Retreat for one. 2nd person, add $25/day. Nestled in our Hawaiian rainforest, the MANGO TREE COTTAGE deepens restoration & inspires creativity. Month-long retreat stays are greatly encouraged, with 30% discount off daily rate. 15% discount for 2 wk. retreats. One week minimum stay. W&F zazen meditation. Mon. & Th. Yoga. Settle. Ground. Experience "old Hawaii," & be profoundly transformed.

Top Guest favourite
A guesthouse is positioned on a cliff overlooking the ocean, surrounded by lush greenery. Large windows reflect a warm glow from inside, contrasting with the twilight sky. The scene captures the tranquil atmosphere of the Hamakua Coast, framed by trees and plants.
Bungalow in Pepeekeo
4.97 out of 5 average rating, 408 reviews

Heavenly Hakalau: Oceanfront Cliff House

Hamakua Coast living at it's best! Comfortably accommodating 4 guests, the guesthouse is situated on a cliff with unobstructed ocean views. Air conditioning in both rooms, ensures that everyone is comfortable after a day of island fun. Enjoy stargazing on clear nights, watching whales during whale season or just enjoying the sun and tradewinds. Minutes from ziplining, waterfalls, botanical gardens and just 16 miles north of Hilo. No children under 12 years old.

Top Guest favourite
An open living space features a comfortable sofa facing a large area rug. A dining table is positioned next to a window, with a staircase leading to a loft area above, which is illuminated by natural light. Modern appliances are visible in the kitchenette.
Farm stay in Honomu
4.99 out of 5 average rating, 86 reviews

Lychee Orchard Hideaway (Cottage w/AC and Laundry)

Welcome to our Lychee Orchard Hideaway on the Hamakua Coast. This unique space is surrounded by lush lychee orchards, offers tranquility and 100% privacy. Conveniently located 15 minutes north of Hilo off Highway 19, this cozy space provides the perfect escape. Whether it's for a romantic getaway, a nature retreat or to explore the island, our hideaway offers a genuine experience. Book now. Reconnect! Please read "Other details to note" regarding accessibility.

Guest favourite
A country kitchen area features wooden shelving with colorful kitchenware and appliances. A cozy sitting area includes a blue chair with a patterned throw. Large glass doors open to an outdoor view, framed by vibrant curtains and tropical wall decor.
Guest suite in Papaikou
4.97 out of 5 average rating, 197 reviews

Puumoi Ocean View Hideaway

Puumoi ocean view hideaway is a colorful and comfy one bedroom accommodation that boasts some of the best sunrise views on Hamakua coast. The bedroom has a cheerful feel and the King sized bed is set up for a restful sleep. The bathroom is airy and brightly decorated with hues of blue. A country cozy kitchen is simplified for your use. A fold out sofa is available in the the sitting area as well for extra guests. Come enjoy a bit of Hawaiian country....

Popular amenities for Wailea holiday rentals

  1. Airbnb
  2. United States
  3. Hawaii
  4. Hawaii County
  5. Wailea