Vacation rentals in Wailea

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Top-rated vacation rentals in Wailea

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Top guest favorite

A serene private lanai showcases a bespoke hanging bed adorned with turquoise cushions. The outdoor space offers views of lush greenery and expansive lava fields, with the deep blue ocean visible under a bright sky.

Farm stay in Pāhoa

4.99 out of 5 average rating, 159 reviews

Pohoiki Kipuka Ocean Views from the Lava's Edge

Experience a Hawaii most visitors never see. The 2018 Kilauea Volcano eruption transformed our landscape creating a place of otherworldly beauty, where Creation and Destruction are in full view. "Pohoiki Kipuka" a green island in a sea of lava, an Eco-friendly retreat that provides refuge and resilience. Your bespoke accommodation features ocean and lava vistas on a secluded 6 acre farm behind a private gate. We are 2.5 miles from Issac Hale Beach Park, swimming and thermal heated warm ponds.

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, 227 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

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, 200 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.

Guest favorite

An aerial view showcases a spacious property with a tropical style home set against a backdrop of the ocean. A manicured lawn surrounds the residence, featuring a small gated pool and a gazebo. Lush vegetation and palm trees enhance the landscape, contributing to the private atmosphere.

Home in Pepeekeo

4.87 out of 5 average rating, 177 reviews

Hamakua Coast Tropical Home

A beautiful tropical style custom home featuring private ocean views and a small gated pool. Our home was thoughtfully designed to maximize Hawaiian indoor/outdoor living and entertaining in a manicured park-like setting. A palm lined driveway leads you to a single level 3 bedroom, 2 1/2 bath residence located in the exclusive Pepeekeo Point subdivision, approx. 15 minutes from Hilo. Featuring a fiberglass pool with a bamboo pavilion& bbq for outdoor dining No parties or unregistered guests

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, 406 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

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, 178 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.

Superhost

The exterior of a two-story A-frame ranch house features red wooden siding and a green metal roof. A spacious deck is visible with outdoor seating and tables, offering views of the surrounding landscape. Lush greenery encircles the property, enhancing the natural setting.

Cabin in Pāpa‘aloa

4.84 out of 5 average rating, 409 reviews

Horses and Waterfalls

E komo mai - welcome! When you need or want complete relaxation with your own private waterfalls, pools and ocean view stay at Horses and Waterfalls and enjoy Hawai’i style country living at its best! During your stay I highly recommend the Papaaloa Country Store and Restaurant just down the road. They have great pizza and fresh locally grown foods and local style menu. They usually have live music 3 nights a week . Hope to see you on our calendar soon ! Aloha - Keith and Ashley

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, 254 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 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, 101 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

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, 386 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

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

4.98 out of 5 average rating, 133 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.