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
The image features a serene pool area surrounded by lush tropical landscaping. Sun loungers are positioned near the custom Lava Rock Pool, which is complemented by natural rock formations. A wooden bridge leads over to the lush greenery, enhancing the secluded feel of the space.
Guesthouse in Keauhou
4.83 out of 5 average rating, 121 reviews

Lani Wai Ka Napo'o

Incredible Ocean View with Year Round Sunset Views, Beautiful Private Home is set within 1 ¼ acre Secluded Hawaiian Tropical Landscape, featuring a custom Lava Rock Pool (solar heated) & Lava Rock Hot Tub. Property is very private in a quiet neighborhood. Located near Keauhou Shopping Center which has many top amenities, KTA Grocery (local chain), CVS Drugs, Kenichi’s (top Sushi and Japanese Rest.), Regal Movies, Habanero’s (auth. mexican food), Royal Thai Rest. Urgent Care, Specialty Shops!

Top Guest favourite
Lush greenery surrounds a well-maintained lawn that leads to a vibrant blue ocean. Palm trees and tropical plants enhance the natural setting, with gentle waves seen in the distance. The scene captures the essence of a serene waterfront environment.
Guesthouse in Keauhou
4.96 out of 5 average rating, 108 reviews

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.

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, 176 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, 209 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, 785 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

Top Guest favourite
The exterior of the cottage is illuminated by string lights, creating a soft glow in the evening. A spacious porch with a lattice railing leads to the entrance, and well-maintained landscaping surrounds the home, highlighting the welcoming atmosphere.
Guesthouse in Kailua-Kona
4.98 out of 5 average rating, 122 reviews

KoKo Cottage: Adorable 2-Bedroom Ocean View/Lanai

Enjoy our beautiful cottage all to yourself at a cool and breezy 1400' elevation just 10 minutes from town and minutes up the mountain from the Kona International Airport. Relax at the end of a fun day of adventure with a glass of wine on the spacious lanai while you watch the sunset. Our cottage is a perfect base for exploring, whether you want to have fun in beautiful Kailua-Kona or head north to some of the world's most spectacular beaches we're located conveniently between the two.

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, 399 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, 138 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.

Guest favourite
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, 830 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, 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 .

Guest favourite
A spacious room features a large bed adorned with a blue floral quilt. Natural light enters through sliding doors, leading to a private balcony. A flat-screen TV is positioned on a wooden stand across from the bed, and a decorative mirror enhances the room's openness.
Guesthouse in Kailua-Kona
4.87 out of 5 average rating, 433 reviews

Plumeria Studio; Garden Balcony, Close to Airport

Kailana Cottage includes two separate rental units that share a hallway. These units are freshly remodeled, super clean, fresh and new. This unit is called Plumeria, it is set up like a hotel room; spacious room with King sized bed, large bright bathroom, TV, and kitchenette on the screened in balcony to enjoy tropical sunsets and breezes. The kitchenette has a hot plate, microwave, coffee press, tea/coffee, mini fridge along with utensils, plates, pans, etc.

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, 108 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, 143 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.

Popular amenities for Kailua-Kona guesthouses

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Avg. price$285 NZD$313 NZD$276 NZD$264 NZD$271 NZD$262 NZD$248 NZD$245 NZD$252 NZD$281 NZD$268 NZD$294 NZD
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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 $174 NZD 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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