Vacation rentals in Wailea

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Top-rated vacation rentals in Wailea

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Guest favorite

A wooden porch extends from the private unit, featuring two simple chairs and a small table. The view showcases a sprawling landscape of aged lava flows, with green vegetation emerging in patches. The entrance is framed by rustic wooden structure, enhancing the natural surroundings.

Guest suite in Pāhoa

4.86 out of 5 average rating, 586 reviews

Lava Lookout: Pele (Hawaiian Goddess of Volcanoes)

Lookout on aged lava flows in paradise with sunny days and pristine starry nights. Enjoy the Milky Way and luxury in an off-grid oasis with water catchment and solar. Here on the frontier where the lava greets the sun is a weekly block party every Wed. & Kehena Black Sand Beach 5.8 miles away. The Pele room is one of four private studios that include the shared kitchen, wifi, and work well for large groups; check out our other listings (Paka’a, Nāmaka, Kāne) to see more reviews and details.

Top guest favorite

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, 224 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)

Guest favorite

The guesthouse is positioned on a grassy area, surrounded by lush greenery. The structure features a covered porch with a seating area, large windows, and a light blue exterior. A small structure is located adjacent to the house, enhancing the serene atmosphere of the property.

Cabin in Pāhoa

4.93 out of 5 average rating, 114 reviews

Junglo Bunglo

Authentic Hawaii experience in a jungle hale that connects you to nature in a magical, isolated, and old area of Puna. This guest house is born from our inspiration and hands, and is well equipped for an off-grid (water+power provided by nature) farm life. We are close to the ocean, about 5 minute drive or 15 minute walk. You can hear the winter humpback whales on quiet nights jump and slap their tales which is fun. 20 minutes from Pahoa; 50 mins from Hilo; 50 mins from Volcano National Park

Top guest favorite

A vibrant sunset casts warm hues of orange and pink across the sky, framed by palm trees and lush foliage. The horizon reveals distant hills, creating a serene backdrop to this tranquil outdoor scene.

Guesthouse in Honomu

4.95 out of 5 average rating, 65 reviews

ILIOPUA Paradise found

Want to stay on a secluded, gated 45 park like acres bordered on two sides with streams? One is a full time running stream and the other has seasonal waterfalls. Lots of hiking so you can get your exercise without having to leave the property. The original owner had dreams of having a botanical garden so there are many varied plants. We even have goats and chickens. Start the day with range free eggs and a bit of fruit—oranges, tangerines, bananas, lemons, limes, and more—paradise found!

Top guest favorite

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, 36 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.

Top guest favorite

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, 198 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 favorite

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, 404 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 favorite

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, 251 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 favorite

The studio space features a spacious bed adorned with a colorful quilt, accompanied by a woven bench. A comfortable reading chair is positioned near a table with chairs, while large windows provide views of the lush greenery outside.

Guesthouse in Hakalau

4.97 out of 5 average rating, 63 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 favorite

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, 383 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 favorite

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

4.98 out of 5 average rating, 60 reviews

Lychee Orchard Hideaway (NEW 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 favorite

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

4.95 out of 5 average rating, 154 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!