
Holiday houses in Wailea
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Top-rated holiday rentals in Wailea
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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.

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.

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)

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!

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.

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

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.

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.

Cozy Ocean View Home with washer/dryer on farm
Experience the island life on the luscious and quiet Hamakua Coast. Wake up to the sound of birds, enjoy cup of coffee with breathtaking 180 degrees ocean views and taste fresh fruits straight from our trees. A quiet escape away from the city where you can relax and reconnect with nature. *Comfortable room and a fully equipped kitchen. *Garden with fruit trees (around 60 trees) * Free Wi-Fi, parking. fresh linens *Local tips for the beaches and hikes.

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.
Popular amenities for Wailea holiday rentals
Other great holiday rentals in Wailea

Hilo Bay Room at the Hamakua Chocolate Farm

Cozy Aloha Room

Oceanfront "Treehouse" at Hakalau with Kitchen

Inn at Akaka Falls - 15 Minutes to Hilo - Rm#5

Aloha Nature Lovers

Pua's Patch: The Tivaevae Room

Wild Life Habitat Eco Village - AIR

Hawaiian Dream with Pool
Destinations to explore
- Hapuna Beach
- Mauna Lani, Auberge Resorts Collection
- Kaunaoa Beach
- Mauna Kea Golf Course
- Waikōloa Beach
- Isaac Hale Beach Park
- Mauna Lani Golf
- Volcano Golf and Country Club
- Carlsmith Beach Park
- Waikoloa Beach Golf Course
- 49 Black Sand Beach
- Hapuna Golf Course
- Lava Tree State Monument
- Machida Beach
- Mauumae Beach
- Pololū Beach
- Kahonua
- Kaluhikaa Beach