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
A natural wood cabin is nestled within vibrant greenery, showcasing a welcoming porch with wooden steps. Surrounding foliage includes lush tropical plants, creating a serene and secluded atmosphere underneath a light canopy.
Cabin in Pāhoa
4.96 out of 5 average rating, 180 reviews

Jungle Haven at ReKindle Farm

Surrounded by fruit trees and lush greenery, ReKindle offers a peaceful retreat for those seeking to reconnect and restore. A 15 minute walk to the ocean, our cabin tucked in the jungle is the perfect place for guests to unwind and immerse themselves in nature. Fully sustainable, while still providing luxury and comfort. Whether you're looking to relax in a peaceful setting, learn about permaculture, or visit our farm, we have something for everyone. Jungle Haven is off grid and on solar power.

Top Guest favourite
The log cabin is positioned on a hillside surrounded by lush greenery, featuring a blend of vibrant trees and tropical plants. A clear sky adds to the natural tranquility of the setting, highlighting the cabin's wooden exterior and nearby landscaping.
Guesthouse in Honokaa
4.97 out of 5 average rating, 290 reviews

Romantic waterfall cabin in the rain forest

Your own private log cabin and waterfall! Listen to the rushing stream as it cascades over your own private 50 foot high waterfall in your own private cabin. For the writer. For the dreamer. For the romantic getaway. Be inspired, transported and immersed into our Hamakua Coast rain forest oasis. Located next to the Waipio Lookout, our rain forest property is the perfect place to recharge and rejuvenate. We’re a ten minute drive to Historical Honoka’a Town. Our "Banana Belt" climate is perfect!

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, 236 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 and 5 miles to the airport. The perfect balance of being in the country and close to everything! We are close to black sand beaches, surf, botanical gardens and waterfalls! The Hilo farmers market is 2 miles away! Come and relax in the hammock on the lanai with tropical breezes! (Please note there are entry stairs)

Top Guest favourite
The interior of the octagon-shaped Treehouse features a spacious bed adorned with a decorative throw and pillows. Wood paneling offers a warm ambiance, while natural light filters through skylights and windows. A vintage dresser with a mirror complements the rustic decor.
Farm stay in Papaikou
4.95 out of 5 average rating, 168 reviews

Zen Treehouse Private Retreat & Farm Stay

Retreat to a Zen-like setting in the Trees! BRAND NEW (11/24) KING BED w/ DUAL BEDJET air systems for the most comfortable sleep surrounded by nature. Retreat to a Zen-like setting in the trees, slow down and relax in this beautiful redwood octagon artist studio on a working coffee, vanilla and chocolate farm. Private lanai in the treetops tucked into a tropical rainforest. Watch the stars or stream from bed. Wake to birdsong; de-stress, meditate, read, write, dance, create and breathe!

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, 202 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
A tranquil waterfall cascades over dark rocks into a serene swimming hole surrounded by lush greenery. A person is seen swimming in the calm water, while others relax on the rocky edge, engaged with the natural surroundings.
Farm stay in Hakalau
4.95 out of 5 average rating, 411 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!

Guest favourite
An outdoor deck features a large dining table paired with long benches and cushioned chairs, offering ample seating. Scenic views of lush green fields and the ocean are visible in the background, illuminated by the warm glow of a sunset.
Home in Pepeekeo
4.88 out of 5 average rating, 179 reviews

Renovated kitchen & Ocean Views

For the price of a hotel room (i.e. 1-2 rooms), you get a home that fits 6 people with beautiful scenic ocean views & a renovated kitchen! This bright & airy 3 bedroom, 2 bath home features a large outdoor deck that fits the entire family overlooking the Pacific Ocean, green pastures and starry skies. Great for families & groups. This 24-acre property comes complete with a meandering stream, lychee, rambutan, longan, coffee trees and gentle farm animals playing behind the fence.

Top Guest favourite
Lush greenery frames the scene with tall palms swaying gently by the ocean. In the distance, waves roll onto rocky shores beneath a soft sky, where a faint rainbow arcs gracefully over the shimmering water.
Guesthouse in Hakalau
4.96 out of 5 average rating, 256 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.

Guest favourite
The spacious living area features comfortable seating with floral-patterned upholstery, a light-colored area rug, and a glass coffee table. Large windows allow natural light to fill the space, complemented by tropical views and wooden blinds. Artwork hangs on the walls, enhancing the room's decor.
Home in Pepeekeo
4.94 out of 5 average rating, 103 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.

Guest favourite
A vibrant rainbow arches over the shimmering Pacific Ocean, visible from a lush green lawn. The scene includes rocky coastal formations and nearby tropical vegetation, creating a serene backdrop that invites relaxation and appreciation of the natural beauty.
Home in Laupahoehoe
4.94 out of 5 average rating, 127 reviews

Hamakua BnB, oceanfront cliff house

This is a unique Sea Cliff House above Laupahohoe point with unobstructed panoramic view of the Pacific Ocean from most rooms in the house. We are located along the Hamakua coast between Hilo & Waimea, 80 miles of coastline with exceptional agricultural lands with gulches, waterfalls and abundant flora.   Here, the crashing windward waves of the pacific ocean carve rugged pinnacles into the coastline. From the heights of the home you'll see whales in the winter months.

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, 391 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.

Guest favourite
A cozy living area features a curved sofa with light-colored cushions, inviting relaxation. Natural light fills the space through large sliding glass doors, which lead to a deck. A hanging chair adds a unique touch, while a staircase leads to the loft area.
Guesthouse in Papaaloa
4.96 out of 5 average rating, 163 reviews

Garden Studio with Ocean View

Relax and indulge the serene Hamakua life! Adorable mother-in-law studio on an organic fruit orchard. Built with sustainability in mind, it is supported by solar power & water from the rain catchment. Perfect for the eco minded travelers who like the comfort of having amenities. The sleeping loft and the lanai face a grand view of the ocean surrounded by fruit trees, tropical garden and farm animals. This studio is one of a kind, will promise you an amazing stay!

Popular amenities for Wailea holiday rentals

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