Guest house holiday rentals in Kailua-Kona

Kona Ocean Front Cottage on Keauhou Bay

Waterfront cottage on private, gated 1 acre estate. Close as you can get to an over the water bungalow in Hawaii with direct ocean access to swim, surf, kayak, snorkel and watch dolphins. Walking distance to manta ray, snorkeling, kayak, whale and dolphin tours, golf, restaurants, movie theater, and outdoor art market. Two room suite. Queen bed. Living room with 50 in TV. Bathroom with large shower. Large covered deck with seating area, kitchenette, dining table, lounge chairs. Outdoor shower.

Private Kona Oceanview Retreat with parking

Escape to a private oceanview retreat on a quiet Kona hillside — where mornings begin with Pacific views from your own lanai, and evenings end in what guests call "the best shower of my life." This standalone 600 sq ft guesthouse has its own private entrance, queen bed, full kitchen, and spa bathroom with rainfall shower and bidet. Beach chairs, snorkels, masks, umbrella, and cooler all included. Minutes from Alii Drive and Kona's best beaches. 15 min to Kona Airport. 2-night minimum.

Treehouse Ohana

The Ohana in a tropical jungle setting will be your home while visiting the Big Island. We are located at 1000ft elevation, and it's a nice few degrees cooler than downtown Kona. In 10 minutes you can get to the closest beaches by car. Start your day with a freshly brewed cup of James Bean Coffee from our farm. You have your own private entrance to the Ohana and free parking for 1 car. Enjoy the jungle & animal sounds and ocean view. No A/C, no self check-in. Cats & dogs on premises.

Spectacular Views of Kailua-Kona

Aloha and e komo mai to our Ohia Guest House in beautiful Kailua-Kona. Ohia Guest House is your well equipped home away from home, it has everything you will need for a comfortable holiday on The Big Island. We live at a cooler elevation of 1000 feet with pleasant tropical breezes. Our property is on 1.5 acres of tropical landscaping. Ocean views abound, perfect for sunset watching and seeing real-time surf conditions. In the evenings enjoy stargazing and the sounds of the tropics.

Charming Cottage

This quaint & private little cottage is in the Kaloko native Hawaiian forest of Kailua-Kona on the Big Island of Hawai’i. Less than 15 minutes from Kona Airport & less than 15 minutes from town (6.7 miles). Not located in town. Elevation is approx. 2200 ft above sea level. Great if you are looking to experience a tropical forest. Due to severe allergies we are unable to host any animals. Not suitable for children. Must use phone navigation to locate as we are in a rural area :)

Romantic Treehouse Cabin: Birdwatching Hike Yoga

Tucked high above Kailua-Kona in Hawaii’s enchanting cloud forest, this peaceful retreat invites you to slow down and reconnect with nature. Wake to song birds, sip coffee surrounded by lush tree ferns, and enjoy cool mountain air for sleeping( (no air conditioning needed!) Stunning glowing sunsets. Perfect for romantic escapes, creative retreats, or quiet relaxation, this serene hideaway blends tropical beauty, privacy, and cozy comfort into an unforgettable island experience.

Big Lanai w/ outdoor living! Ocean view & breezes!

Ocean Sunset Views and breezes on the spacious Hawaiian style outdoor living Lanai! Fully equipped Kitchen – including filtered water, and several small appliances 2 Bedrooms - queen size beds. Futon can also be used for sleeping. Overhead fans in every room. Bathroom w/ double shower. Outdoor shower too! Private entrance, driveway, carport Lovely residential Keahou neighborhood 5 Minute drive to Beaches – swimming, snorkeling and surfing Wifi and Netflix Laundry

Fresh & Bright Tropical Getaway- Ocean View

Aloha and Welcome to our cozy ohana. You can expect clean, comfy, modern, with lots of light in this spacious guest suite. The accommodation is in a quiet and safe neighborhood with convenient parking. At a higher elevation, the area is much cooler and breezier than staying in town and you can fall comfortably asleep in our comfortable queen-sized bed, listening to the sounds of coqui frogs and waking up to the beautiful sound of birds. We hope you enjoy your stay with us!

Kealakekua Bay Bali Cottage -steps from Bay

This hidden jewel is at Kealakekua Bay. Private setting in our lower backyard. Walk to nearby Manini Beach. We are located 4 miles down at the bottom of Napoopoo Rd Fully equipped outdoor kitchen. Gas stove, refrigerator/freezer. Living/Dining area and bedroom/vanity area enclosed with open area at roofline where a large ficus tree limb goes through. Outdoor shower/ wc area. Very Private. Daily pricing includes Hawaili State taxes, 11% TAT and 4.5% GE .

Mango Hale Cottage

Listed price is for 2 guests. An additional charge of $40/nt for an extra guest. Mango Cottage is an original beach house located at the private and quiet end of Puako Beach Dr. The Cottage is a minute walk to the Paniau beach access which is a well known and popular beach for snorkeling, surfing, and fishing. The property is shared with the main house(Mango Hale) and surrounded by a lush lawn, mango & coconut trees, which provide a cool & comfortable environment.

Our Hawaii Hale: Detached 2 bed ohana with parking

Our Hawaii Hale sits at 1500’ elevation and is 10 minutes from the airport, beaches and downtown Kona allowing for easy access to everything the island has to offer! Our unit features 2 full beds, a kitchenette and large bathroom with walk-in shower. Enjoy parking right outside of unit, beach gear & shared laundry! We are in a residential neighborhood with roosters and coqui frogs. TA-106-058-1888-01

Kona Ohana: AC, Dual-Monitor Office, Patio & BBQ

Sun-kissed mornings at Magic Sands, hammock naps under swaying palms, and gigabit-speed Wi-Fi when duty calls—that’s the rhythm of life at our private 510-sq-ft Ohana in Kona. Whether you’re a couple chasing sunsets, a family building sandcastles, or a remote worker dialing in from paradise, this stand-alone guesthouse is your home base for effortless island living.