Vacation rentals in Wailea

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.

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.

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)

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!

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.

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.

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!

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.

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.

The Phoenix House - Epic GEM on Volcanic LavaField

Come celebrate your Life & new beginnings at the acclaimed Phoenix House! Featured in countless media, this epic, off-grid tiny home creation at the feet of an active Volcano has won the hearts of countless international visitors.. Enjoy a magic, memorable vacation in this unique, custom made tiny temple on some of the newest land on Earth ~ This custom tiny house was designed by Will Beilharz and built by ArtisTree Homes. Considerate Caretaker lives nearby on site.

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.

Peaceful Rainforest Treehouse Retreat

Our Retreat is a labor of our love and was built as such. A getaway to relax, hike the nearby beaches, forests, and volcanoes and to simply enjoy life. Our place is a peaceful spot completely off the grid in nature. It is 8 miles to Hawai'i Volcanoes National Park. You’ll love our place because of the location, the ambiance, and the outdoor space. Our goal was to bring the outdoors in and the indoors outside. Our place is good for couples and solo adventurers.