Vacation rentals in Wailea

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Top-rated vacation rentals in Wailea

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Top guest favorite
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, 190 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 favorite
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, 301 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!

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, 609 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.

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, 204 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, 419 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 favorite
A circular pool with crystal-clear water is surrounded by lush greenery, including tall ferns and vibrant tropical plants. Sunlight is reflected on the water's surface, creating a serene atmosphere. A wooden deck provides access to the pool, enhancing the natural setting.
Guesthouse in Keaau
4.96 out of 5 average rating, 267 reviews

Magical Jungle Cabin with Pool

Nestled in a lush guava tree grove, this tropical sanctuary offers the nature sounds of camping with the comforts of a cozy bungalow. Perfect for a couple's getaway, a personal retreat, or a peaceful place to retire to after a full day of exploring. Wake up with an outdoor rainfall shower, soak up the Hawaiian sunshine while you float in the pool, grill locally caught fish in the kitchenette pavilion (hot plate and BBQ), and stargaze some of the darkest night skies. Primary residence.

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, 260 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 favorite
Home in Pepeekeo
4.94 out of 5 average rating, 107 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 favorite
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 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, 398 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 favorite
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, 190 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....

Guest favorite
A small guest shack is surrounded by vibrant flower beds featuring an array of colorful blooms. Lush banana trees provide shade, while a covered carport extends from the building. The structure is set against a backdrop of green foliage, creating a serene rural setting.
Guesthouse in Kurtistown
4.97 out of 5 average rating, 155 reviews

Country Guest Home

(REF TAX ID TA005-218-0480-01) Enjoy time in a small (384 sq ft) self-contained guest shack with full kitchen in a rural setting. If you don't find the sound of coqui frogs at night obtrusive to your sleep, then this space would be suitable. While you will have privacy, my dad stays in the main house in case you need assistance in person. We are located at about 100 foot of elevation which provides for relatively cooler nights.

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