Guesthouse vacation rentals in Kailua-Kona

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Top-rated guesthouses in Kailua-Kona

Guests agree: these guesthouses are highly rated for location, cleanliness, and more.

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Guest favourite

Guesthouse in Holualoa

4.93 out of 5 average rating, 440 reviews

The Outlook Ohana-King

For The Island Adventurer Or A Romantic Getaway for two AMAZING Ocean Views! Overlooking the vast Pacific Ocean & Kailua-Kona Bay *King Bed 4" topper faces the ocean view *Private Entry *Self Checkin/Checkout *Large Lanai ~ Outdoor Shower with Hot H20 *STARLINK Satellite-excellent *Beach+Bath Towels provided *Bathing essentials provided *Organic Coffee/Tea *Not yet safely set up for children & infants *Mobility is a must *Parking and Pathway are on an incline *Message if you have questions :)

Guest favourite

Guesthouse in Kailua-Kona

4.93 out of 5 average rating, 106 reviews

Mala Ohana House-Garden Suite near epic beaches

Aloha and welcome to our home! This 1 bedroom garden view guest suite is perfectly situated in North Kona. The Mala Ohana house includes a lanai, dedicated parking, private yard,full kitchen,WIFI, Air-conditioning, bbq grill and beach gear. Located about 12 minutes from Kona Town to the south, 10 to 20 minutes from the beaches to the north and 5 minutes from the airport. Great views of Hualalai mountain when it’s not cloudy. Clean, comfortable, and convenient home in a residential neighborhood.

Guest favourite

Guesthouse in Kailua

4.92 out of 5 average rating, 401 reviews

A Piece of Paradise with Ocean Views in Kona

We'd love to share our small piece of paradise with you. Our private studio with ocean views is comfortable, clean and conveniently located. It's decorated with a beach theme to make you feel right at home in Hawaii. The studio is located just above the Wailua Trail in the higher elevation. We get cool nights and ocean breezes but are still only 5minutes to the beach or town. The yard is full of lush tropical vegetation and fruit producing plants such as mangos, avocados, tangerines and lemons.

Guest favourite

Guesthouse in Kailua-Kona

4.97 out of 5 average rating, 340 reviews

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.

Guest favourite

Guesthouse in Captain Cook

5 out of 5 average rating, 101 reviews

Pebble Beach House- 2 Minute Walk to the Beach!

Come enjoy our guest house with Pebble Beach just a 2 minute walk down the road! Our piece of paradise is located in a peaceful neighborhood where you can see and hear whales spouting and slapping their tails (in season) and enjoy ocean sunsets. Pebble Beach is a great place to snorkel, kayak, or start a hike along the Kings Trail to volcanic formations or a hidden black sand beach. We are located approximately 45 minutes south of Kona, and 75 minutes to Volcanoes National Park.

Guest favourite

Guesthouse in Kailua-Kona

4.99 out of 5 average rating, 151 reviews

Elegant & Peaceful Studio

Tucked away in a friendly, family neighborhood at a cool elevation, this island jewel will provide you with a relaxing place to come home to after a satisfying day of adventures to anywhere on the Big Island. Hale Moa studio is situated next to our family home in a small cul-de-sac. Come enjoy spectacular views of the sun setting over the ocean out front, or relax and fire up the grill in the backyard on your own private patio. We love this spot and hope you will too!

Guest favourite

Guesthouse in Kailua-Kona

4.96 out of 5 average rating, 556 reviews

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. 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 :)

Guest favourite

Guesthouse in Kailua-Kona

4.93 out of 5 average rating, 445 reviews

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.

Guest favourite

Guesthouse in Kailua-Kona

4.95 out of 5 average rating, 329 reviews

Cottage with Ocean and Sunset view

Situated on the island's western side at a cool 1300ft elevation, this small cottage is suitable for two people. Privacy is the keyword. This is a quiet, clean, peaceful place with A/C. It is near the airport, town, and beautiful beaches, located in a safe, affluent neighborhood. After the lava eruption on the other side of the island in 2018 subsided, we are now thrilled to have the best air quality and blue skies since 2007!

Guest favourite

Guesthouse in Kailua-Kona

4.96 out of 5 average rating, 183 reviews

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

Guest favourite

Guesthouse in Kailua-Kona

4.95 out of 5 average rating, 104 reviews

Cozy Vintage Inspired Hawaiian Guest Cottage

7 minutes from the airport and 9 miles from downtown Kona, this stylish, cheerful guest cottage is perfectly situated for exploring all this island has to offer! The vintage art/decor nod to a paradise of yesteryear with both mid-century flare and old Hawaii charm. It has a kitchen, queen bed, 55” smart tv, private patio and shared bbq. Come and make where you stay as memorable as the places you go.

Guest favourite

Guesthouse in Kailua-Kona

4.98 out of 5 average rating, 205 reviews

Hawaiian Mt. Retreat Suite A

Enjoy a tranquil stay in our well equipped cottage....we tried to think of everything so you can relax. It is centrally located between warm sunny beaches and cool mountain hikes. You're just miles from the popular downtown Kailua-Kona, food, shopping, & ocean sunsets. Come visit Hawaii island style and soak it all in.