Guesthouse holiday 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
A vibrant green cottage is surrounded by lush tropical vegetation. Steps lead up to a covered porch with white railings, offering access to the main entrance. The exterior reflects a charming, rustic style, set within a serene garden brimming with diverse plants.
Guesthouse in Captain Cook
4.92 out of 5 average rating, 172 reviews

Garden Cottage Ohana

Welcome to your small slice of paradise! Newly redone kitchen, LR, and bathroom! The garden cottage is surrounded on three sides by dense forest. Enjoy coffee and sunsets on your private porch overlooking our tropical fruit farm, the ocean, and stargazing skies. Birds singing, a chorus of frogs, and a wild rooster’s crow are just some of the “sounds of the jungle” that will surround you. The cottage sits between two beautiful bays that host some of the best snorkeling of the Hawaiian Islands.

Top Guest favourite
A spacious living area features large windows with stained glass accents, allowing natural light to fill the room. A comfortable seating area is situated beside a wooden coffee table, and a staircase leads to the upper level. Sliding glass doors provide access to the outdoor environment.
Guesthouse in Kailua-Kona
5 out of 5 average rating, 208 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!

Top Guest favourite
A private lanai is enclosed by a decorative railing, offering expansive views of the ocean and vibrant tropical plants. Wicker seating is arranged for relaxation, complementing the serene outdoor setting bathed in natural light.
Guesthouse in Kailua-Kona
4.97 out of 5 average rating, 777 reviews

Private Kona Oceanview Retreat with parking

Escape to a private oceanview retreat in North Kona! This cozy guesthouse offers breathtaking views from your private deck, surrounded by lush tropical plants. Enjoy your morning coffee while soaking in the serene ocean scenery, and unwind in a tastefully decorated interior with all essentials, a well-equipped kitchen, modern bathroom with a luxurious shower, and convenient laundry facilities. Perfect for couples or solo travelers and easy access to Kona’s attractions! Tax ID W01822068-01

Superhost
A charming cottage constructed with intricate antique Bali panels is surrounded by lush greenery. The outdoor living area features seating arrangements under a partially covered roof, with soft lighting highlighting the unique decor and inviting atmosphere.
Guesthouse in Captain Cook
4.81 out of 5 average rating, 825 reviews

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, under counter 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, 10.25% TAT and 4.25% GE .

Guest favourite
A view from the property showcases lush grass leading to a path. Beyond the neatly trimmed hedges, the ocean sparkles in the distance under a clear blue sky, complemented by scattered clouds and greenery along the hillside.
Guesthouse in Kailua-Kona
4.97 out of 5 average rating, 394 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.

Top Guest favourite
An outdoor dining area is featured on a private lanai, with a glass table and four black chairs. A blue decorative bottle sits at the center of the table. Scenic ocean views are visible in the background, complemented by clear skies and distant coastline.
Guesthouse in Kailua-Kona
4.99 out of 5 average rating, 134 reviews

Kona Guesthouse ❤ Ocean Views | Kitchen | Patio

Enjoy all the comforts of home with sweeping views of Kailua Kona. Start your day with a brisk morning walk in our friendly neighborhood walking trail. When you are ready to get out and explore, you are minutes away from attractions that bring people to the island. Snorkel amidst turtles and reef fishes in Kahaluu Beach. Try night diving among Manta Rays in Keauhou Bay. Drive south to Kealakekua Bay and snorkel in one of the best spots known for its spectacular coral reefs.

Top Guest favourite
The studio cottage is nestled at an elevation, featuring a green exterior with red trim. A wide covered lanai is accessible via steps, offering a shaded space for relaxation. Large windows provide ample natural light, enhancing the cottage's welcoming appearance among surrounding greenery.
Guesthouse in Holualoa
5 out of 5 average rating, 265 reviews

Holualoa Studio Cottage - Incredible Ocean Views!!

BETTER THAN THE REST!!! Our adorable studio cottage is located on the side of Hualalai Mountain in Holualoa, Kona Coffee growing country. We are just above Kailua-Kona town, and only about 12-15 minutes to shopping, and about 15 minutes to the closest beach and only 20 minutes to the airport. You will LOVE our panoramic ocean and coastline view, plus on clear days you can see Mount Hualalai right behind us, plus a beautiful coffee farm too. Read our reviews!

Top Guest favourite
The living area features a sleek, modern design with a comfortable sofa bed and a wooden coffee table. A small dining bar with two stools complements the compact kitchen, which is equipped with essential appliances. Light walls and decorative plants enhance the bright, inviting ambiance.
Guesthouse in Kailua-Kona
5 out of 5 average rating, 105 reviews

Hale Kamalei in Kailua Kona

Enjoy all the comforts of home in this stylish guesthouse in the heart of Kailua Kona. This detached one bedroom ohana is centrally located - just minutes from the airport, shops, restaurants and some of the best beaches on Hawai'i Island. Experience Hawaii away from the hustle and bustle of resorts and overcrowded condominiums and stay where the locals live! The designated parking space is just steps from the front door. Private, clean, and convenient.

Top Guest favourite
Guesthouse in Kailua-Kona
4.98 out of 5 average rating, 141 reviews

The Banyan House

Offering a newly renovated & private 1 bed, 1 bath guest suite conveniently located in a friendly residential area in Kona, close to beaches and restaurants. You have your own separate entrance to the unit, although we do share a wall, as this Ohana is connected to the main house. Please note that there are stairs and a pathway coming up to the property, guest should be comfortable walking up the path with their belongings and bringing them up stairs.

Top Guest favourite
The cottage is seen nestled among a vibrant flower garden, featuring a variety of colorful blooms including sunflowers. Lush greenery surrounds the area, enhancing the natural setting and providing a serene atmosphere.
Guesthouse in Kailua-Kona
4.96 out of 5 average rating, 369 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!

Top Guest favourite
The exterior of the unit is shown, featuring a covered porch, two entrances, and large windows for natural light. A parking spot is conveniently located nearby. Lush greenery surrounds the building, enhancing the tropical setting. Outdoor seating is visible on the porch.
Guesthouse in Kailua-Kona
4.95 out of 5 average rating, 256 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
A bright living area features turquoise walls complemented by a pink sofa and a natural wood coffee table. A mounted flat-screen TV is positioned against the wall. Natural light streams through a window covered by wooden blinds, and a decorative fan hangs from the ceiling.
Guesthouse in Kailua-Kona
4.94 out of 5 average rating, 143 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.

Popular amenities for Kailua-Kona guesthouses

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Avg. price$251 AUD$275 AUD$243 AUD$232 AUD$238 AUD$231 AUD$219 AUD$216 AUD$222 AUD$248 AUD$235 AUD$258 AUD
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Quick stats about guesthouse rentals in Kailua-Kona

  • Total holiday rentals

    Explore 40 holiday rentals in Kailua-Kona

  • Nightly prices starting at

    Kailua-Kona holiday rentals start at $153 AUD per night before taxes and fees

  • Verified guest reviews

    Over 4,670 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Kailua-Kona holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Kailua-Kona rentals

  • 4.9 Average rating

    Kailua-Kona stays are highly rated by guests—averaging 4.9 out of 5!

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