Guesthouse vacation rentals in Kailua-Kona

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Top-rated guesthouse rentals in Kailua-Kona

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

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Guest favorite

Guesthouse in Holualoa

4.93 out of 5 average rating, 445 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 favorite

Guesthouse in Kailua-Kona

4.94 out of 5 average rating, 112 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 favorite

Guesthouse in Kailua-Kona

4.97 out of 5 average rating, 178 reviews

Tiny House in Kona - 5 Minute Walk to the Beach!

Mahalo nui for your Interest! After a year-long break, I am happy to be back hosting this wonderful space ~ Click my profile to check my 1000+ 5-Star Reviews and book with Confidence! This is a real Tiny House on Wheels with an additional connected open air and fully screened kitchen for dining and relaxing. You'll love this "rustic" and private experience in an upscale neighborhood just 4 miles south of downtown Kona! And, you are only a 5 Minute Walk to Magic Sands - the best beach in town!

Guest favorite

Guesthouse in Kailua-Kona

4.99 out of 5 average rating, 146 reviews

Romantic Cabin Treehouse in Hawaii Cloud Forest

Stay in a unique cloud forest at a 2500 foot elevation, yet minutes to airport, beaches, restaurants, bars and shops. Extraordinary lodging, perfect for a honeymoon, writers retreat or meditation vacation. Surrounded by native forest, with tree fern and Hawaiian song birds. Afternoon rains end in grand sunsets. Nights are cool for sleeping with windows open. State forest hiking trails are at your doorstep. Great bird watching, including a local flock of cockatoos that visit in the morning!

Guest favorite

Guesthouse in Holualoa

4.95 out of 5 average rating, 110 reviews

Kanaho Place: Holualoa Guesthouse

Aloha! This guesthouse, built in 2020, is nestled on the slopes of Hualalai Mountain on a five acre family hobby farm. We love our location at a cool 2300 ft elevation, very close to Holualoa town, 15 minutes from downtown Kailua-Kona, the airport, and beaches. The space has a large covered upstairs lanai with an ocean view, comfortable queen bed, beautiful bathroom, bonus workspace, WiFi, Smart TV, kitchenette with tabletop oven, microwave, hotplate, full-sized fridge, and outdoor shower.

Guest favorite

Guesthouse in Kailua-Kona

4.97 out of 5 average rating, 153 reviews

AC | 1 Gig | BBQ | Kitchen | Workspace | Hammock

º 510 sq-ft Ohana (guesthouse) with private entrance, AC, Gig WiFi 6E, BBQ, Laundry, Hammock, Backyard, Patio º 5 min drive downtown, 8 mins to Magic Sands Beach º Fully stocked and equipped kitchenette & bathroom º Desk, chair, 2 monitors, printer, wired ethernet & Wi-Fi; Walk-in closet º Beach equipment (chairs, umbrella, towels, snorkels, kids toys & life jackets, coolers, body boards) º Safe, quiet neighborhood; owner lives on site º Honda Pilot, HR-V, CR-V or Kia Sportage SX for rent

Guest favorite

Guesthouse in Kailua-Kona

4.97 out of 5 average rating, 348 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 favorite

Guesthouse in Captain Cook

4.99 out of 5 average rating, 109 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 favorite

Guesthouse in Kailua-Kona

4.95 out of 5 average rating, 155 reviews

Ka Hale O Maluhia

Welcome to your next vacation! Our upstairs guesthouse is private and comfortable. Our reviews speak for itself! We strive to provide our guests with an amazing stay. Wake up every morning enjoying a cup of coffee on the balcony with a panorama view of the ocean. Enjoy your days at the beach using our provided beach equipment (towels, chairs, umbrellas, boogie boards and more). And relax in the evenings, at this cool elevation, next to the fire pit with your family and friends.

Guest favorite

Guesthouse in Waimea

4.94 out of 5 average rating, 124 reviews

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.

Guest favorite

Guesthouse in Waimea

4.98 out of 5 average rating, 208 reviews

“Special Rate” Private, Waimea Ohana (Guest House)

My husband and I purchased our home in 2014 and spent a year remodeling the main house and guest house. Our one-acre property is centrally located on the slopes of Buster Brown on the sunny side of Waimea (also known as Kamuela). We are walking distance to town, grocery stores, local farmers markets, coffee shops and some of our favorite restaurants. At 2750' elevation, our cooler evenings and nights give you a cozy break from the days sunny adventures.

Guest favorite

Guesthouse in Kailua-Kona

4.95 out of 5 average rating, 112 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.