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Guesthouse holiday rentals in Kailua-Kona

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Quick stats about guesthouse rentals in Kailua-Kona

  • Total holiday rentals

    Explore 30 holiday rentals in Kailua-Kona

  • Nightly prices starting at

    Kailua-Kona holiday rentals start at $112 AUD per night before taxes and fees

  • Verified guest reviews

    Over 3,650 verified reviews to help you choose

  • Wi-Fi availability

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

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Kailua-Kona rentals

  • 4.9 Average rating

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

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 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

Plumeria Studio; Garden Balcony, Close to Airport

Plumeria at Kailana Cottage Kailana Cottage includes two separate rental units that share a hallway. Plumeria is set up like a hotel-style room, featuring a king-size bed, bright bathroom, TV, and a unique kitchenette located on the screened-in balcony—perfect for enjoying tropical breezes and sunset views. The kitchenette includes a hot plate, microwave, coffee press, tea/coffee, mini fridge, and basic cookware. Conveniently located near the airport with automated check-in and free parking.

FamilyValueGetting around

4.87 out of 5 average rating, 486 reviews
Top Guest favourite
Guesthouse in Holualoa

The Banyan House

Enjoy a newly renovated private 1-bedroom, 1-bath guest suite in a peaceful residential area of Kona less than a mile from the beach. This stylish ohana has its own separate entrance, lush tropical views, a comfortable living space, kitchenette, in-unit laundry, and a spa-inspired bathroom with a beautiful walk-in shower. 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.

ValueLocationLaundry

4.98 out of 5 average rating, 170 reviews
Top 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

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.

LocationFamilyAmenities

4.93 out of 5 average rating, 201 reviews
Top Guest favourite
A panoramic view showcases lush greenery in the foreground, leading to expansive ocean vistas. The sky is filled with scattered clouds, reflecting a vibrant blue hue over the calm waters. The distant shoreline is visible, highlighting the natural beauty of the coastal landscape.
Guesthouse in Kailua-Kona

All About The View!

A reader's delight! Enjoy paradise in this cozy guesthouse with your own library! You'll have the space to yourself with a private entrance, a lovely lanai to enjoy the sunset, televisions, a well appointed kitchenette, and more! The home is located at a cool and comfortable elevation just 10 minutes from Kona International Airport and 10-15 minutes from downtown Kona. We are a busy family of 4 (+pets) living upstairs. We love providing a home away from home for visitors! TA-018-066-6368-01

LocationFamilyBarbecue

4.95 out of 5 average rating, 98 reviews
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

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. Direct ocean access to swim, surf, kayak, snorkel and watch dolphins. Walk to manta ray, snorkeling, kayak, whale and dolphin tours, golf, restaurants, movie theater, and outdoor market. Two room suite. Queen bed. Living room with 50 in TV. Large covered deck with seating area, kitchenette, dining table, lounge chairs. Outdoor shower. Couples and solo travellers only. No smoking.

FamilyLocationQuiet

4.97 out of 5 average rating, 145 reviews
Guest favourite
Guesthouse in Holualoa

Kona Oceanview Retreat - A/C & Rainfall Shower

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 A/C, 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.

ValueFamilySleep quality

4.97 out of 5 average rating, 824 reviews
Top Guest favourite
Lush foliage frames a stunning ocean view under a bright blue sky. The scene is accentuated by a canopy of green leaves and trees, creating a serene and natural atmosphere. Towering trees and various tropical plants enhance the vibrant landscape.
Guesthouse in Holualoa

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.

FamilyLocationHiking

4.94 out of 5 average rating, 526 reviews
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

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.

ValueFamilyKitchen

4.99 out of 5 average rating, 245 reviews
Top Guest favourite
An outdoor dining area is set with a table adorned with plates and glasses, surrounded by comfortable chairs. The blue walls frame the scene, and palm trees sway gently in the breeze, while a vibrant sunset paints the sky in warm hues over the ocean.
Guesthouse in Keauhou

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

ValueFamilyNearby

4.96 out of 5 average rating, 163 reviews
Guest favourite
A private lanai is captured, featuring a small table set for two. Two chairs are arranged with soft cushions, framed by lush greenery. The ocean view stretches across the horizon under a clear blue sky, providing a serene backdrop for relaxation.
Guesthouse in Holualoa

Sea View Studio Getaway

This newly remodeled, fresh and clean guesthouse is centrally located and has amazing ocean views. Situated in a local neighborhood, this spot is perfect for someone looking to get a more authentic Hawaii experience. The Guesthouse is a large, private studio that contains a full kitchen and bathroom, as well as a spacious covered lanai to take in the stunning Kona sunsets. The closest beach is just a 5 minute drive away. A perfect home base for exploring the island!

LocationHikingView

4.93 out of 5 average rating, 123 reviews
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

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 .

LocationValueAccuracy

4.81 out of 5 average rating, 860 reviews
Top Guest favourite
A bright bedroom features two spacious beds covered in white bedding, complemented by light-coloured curtains that frame the windows. A ceiling fan is positioned overhead, while a black nightstand and a small bookshelf add functionality to the room. Two art pieces depicting scenic landscapes are displayed on the wall.
Guesthouse in Kailua-Kona

Comfort By The Coast

Aloha and E Komo Mai (Welcome) to our Ohana unit (2nd floor), where you will find everything you need while vacationing in paradise 🌺. When you stay at this centrally-located Ohana, you will find everything within walking distance. Within a .8 miles radius, you will find the following: Safeway, Starbucks, gas station, fast food, bars, restaurants, farmers market & downtown Kona/pier. Perfect for a walk, dining, Ironman, or catching breathtaking sunsets.

FamilyLocationCheckout

4.98 out of 5 average rating, 111 reviews

Popular amenities for Kailua-Kona guesthouses

KitchenWifiPoolFree parking on premisesAir conditioning

Family-Friendly guesthouses

Top Guest favourite
Guesthouse in Kailua-Kona

NEW- Lavender Lane-1 Bedroom, 1 Bath, & Air Con

ValueLocationAccuracy

4.87 out of 5 average rating, 217 reviews
Guest favourite
A vibrant sunset casts a warm glow over the horizon, surrounded by lush greenery and colorful flowers. The scene is framed by tropical plants, showcasing a blend of deep pinks, oranges, and purples in the sky.
Guesthouse in Waikoloa Village

Synergy Near Golf & Beach

FamilyValueView

4.95 out of 5 average rating, 464 reviews
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

Cottage with Ocean and Sunset view

ValueLocationComfort

4.96 out of 5 average rating, 393 reviews
Superhost
Aerial view captures the serene coastline of Kealakekua Bay, showcasing deep blue waters fading into turquoise. Lush greenery lines the shore, with scattered residences visible in the foreground. The backdrop features rugged cliffs ascending toward a clear, bright sky.
Guesthouse in Captain Cook

Dolphins visit Kealakekua Bay

ValueFamilyNearby

4.85 out of 5 average rating, 106 reviews
Top Guest favourite
An outdoor sitting area is set on a covered lanai, featuring a table and two chairs. A gas grill is positioned nearby, with potted plants adding natural elements. The lush green lawn surrounds the cozy space, providing a tranquil spot for relaxation.
Guesthouse in Kailua-Kona

Carries Cottage

HospitalityLocationCleanlinessOutdoor spacesQuietComfortBeachSleep qualityNearbyAccuracyDecorGetting aroundIndoor spacesKitchenAmenitiesBarbecueBathroomViewNoiseHikingBackyardConditionValueCheck-inLaundryFamilyWi-FiLong stayBreakfastAir conditioningSolo travelCheckoutTVPetsParkingWalkability

4.89 out of 5 average rating, 287 reviews
Top 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 Holualoa

Spectacular Views of Kailua-Kona

LocationValueTV

4.97 out of 5 average rating, 429 reviews
Top Guest favourite
A well-appointed sleeping area features a spacious bed with a floral-patterned duvet and multiple pillows. A light wood nightstand holds a lamp, and a ceiling fan enhances airflow. Natural light enters from a sliding glass door, complemented by a serene beach-themed artwork on the wall.
Guesthouse in Kailua-Kona

Elegant & Peaceful Studio

LocationValueBarbecue

4.99 out of 5 average rating, 167 reviews
Guest favourite
The cottage is surrounded by lush greenery, set against a clear blue sky. A welcoming porch features white railings, while vibrant plants adorn the exterior. The spacious lawn invites exploration and relaxation, framed by the native Hawaiian forest.
Guesthouse in Kailua-Kona

Charming Cottage

ValueFamilyAir conditioning

4.95 out of 5 average rating, 694 reviews

Guesthouses with a patio

Top Guest favourite
Guesthouse in Kailua-Kona

KoKo Cottage: Adorable 2-Bedroom Ocean View/Lanai

HospitalityLocationCleanlinessComfortBeachFamilyOutdoor spacesKitchenSleep qualityGetting aroundViewIndoor spacesNearbyAmenitiesAccuracyNoiseDecorQuietBathroomAir conditioningCheck-inHikingPetsLong stayConditionCheckoutTVBarbecueLayoutLaundryParkingWalkabilityBreakfastBackyardValue

4.99 out of 5 average rating, 148 reviews
Guest favourite
A charming blue studio is set amongst lush greenery, featuring a welcoming porch with white railings. The open entrance reveals large windows that let in natural light. Surrounding ferns and tropical plants create a serene environment, enhancing the overall peaceful setting.
Guesthouse in Keauhou

“Pineapple Cottage” your true Hawaiian getaway

ValueLocationNearby

4.91 out of 5 average rating, 132 reviews
Guest favourite
Guesthouse in Waimea

Waimea Honu Cottage- Cozy & Relaxing

ValueLocationSolo travel

4.92 out of 5 average rating, 108 reviews
Guest favourite
A spacious bedroom features a king-sized bed with minimalistic decor. Light tones and textured wall art create a serene ambiance. Large windows provide natural light, while greenery is visible outdoors. A ceiling fan and air conditioning unit offer comfort.
Guesthouse in Holualoa

3-min walk to beach | King bed | Newly Renovated!

LocationValueAccuracy

4.92 out of 5 average rating, 142 reviews
Guest favourite
Guesthouse in Holualoa

Luxury Ohana, 60ft Salt Pool,

ValueLocationComfort

4.95 out of 5 average rating, 22 reviews
Top Guest favourite
A private outdoor area is showcased with a clear swimming pool and a jacuzzi, both surrounded by a stone patio. A gazebo is positioned nearby, with comfortable seating visible. Lush greenery borders the space, and the sky is partially covered by clouds.
Guesthouse in Puako

Ohana With Private Pool & Jacuzzi

ValueLocationQuiet

5.0 out of 5 average rating, 83 reviews
Top Guest favourite
Guesthouse in Kailua-Kona

Private Retreat| King+Sofa Bed· XL Deck+Laundry·AC

FamilyLocationCheck-in

4.97 out of 5 average rating, 35 reviews
Top Guest favourite
An inviting entrance is shown, featuring a covered walkway leading to a light blue, cottage-style building. Colorful decorations hang from the porch roof, surrounded by lush greenery. Comfortable seating areas can be seen on the porch, offering a peaceful outdoor space.
Guesthouse in Captain Cook

Cottage w/ 2 priv rms & kit/b (TA-154-746-2656-01)

FamilyLocationSleep quality

4.96 out of 5 average rating, 73 reviews

Guest house rentals with a washing machine and dryer

Guest favourite
A covered outdoor patio area is shown, featuring casual seating and potted plants. A view of the ocean and surrounding palm trees is visible through the open space. The tiled flooring adds a functional element to the area, enhancing the outdoor experience.
Guesthouse in Kailua-Kona

Kimo’s Getaway

LocationValueBarbecue

4.91 out of 5 average rating, 314 reviews
Guest favourite
Guesthouse in Holualoa

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

ValueLocationAccuracy

4.95 out of 5 average rating, 241 reviews
Top Guest favourite
A patio area features a small outdoor dining set with four metal chairs and a table, surrounded by lush greenery. A gas grill is positioned nearby, and large sliding glass doors provide access to the interior. Pebbles line the ground, adding to the natural appeal.
Guesthouse in Puako

Mango Hale Cottage

LocationFamilyCheck-in

4.94 out of 5 average rating, 171 reviews
Guest favourite
The pool area is highlighted by a water slide and surrounded by palm trees under a colorful sunset sky. The shimmering water reflects vibrant hues, creating a serene atmosphere. Lounge chairs are positioned nearby, overlooking the expansive view of the ocean and landscape.
Guesthouse in Keauhou

180 degree ocean view, private pool

HospitalityPoolViewLocationFamilyComfortCleanlinessHot tubGetting aroundKitchenAmenitiesNoiseNearbyBeachSleep qualityAccuracyOutdoor spacesBarbecueBathroomQuietLaundryIndoor spacesConditionCheck-inWalkabilityDecorPetsHikingLayoutLong stayValueAir conditioningWi-FiSolo travelBackyardAccessCheckout

4.88 out of 5 average rating, 163 reviews
Guest favourite
The cozy bedroom features a spacious bed with crisp white linens, complemented by soft pillows. Two large windows provide ample natural light and views of the greenery outside. A comfortable armchair and ottoman invite relaxation, while a ceiling fan enhances airflow in the room.
Guesthouse in Holualoa

Holualoa Ekahi -Country guest house,Taxes included

ValueFamilyBarbecue

4.93 out of 5 average rating, 429 reviews
Superhost
The image captures a serene sunset over the ocean, with silhouettes of palm trees framing the scene. The warm colors of the sunset reflect on the water's surface, creating a tranquil and picturesque atmosphere.
Guesthouse in Captain Cook

Look No Further Hale Nai'a Pink Cottage Kealakekua

LocationValueWalkability

4.9 out of 5 average rating, 243 reviews
Top Guest favourite
Aerial view showcases the expansive greenery of the surrounding hills, highlighting the lush landscape. The neighborhood is characterized by manicured lawns, trees, and a collection of homes, each nestled comfortably in the hillside's natural beauty.
Guesthouse in Waimea

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

ValueFamilyHiking

4.98 out of 5 average rating, 259 reviews
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

Our Hawaii Hale: Detached 2 bed ohana with parking

FamilyValueSolo travel

4.94 out of 5 average rating, 298 reviews

When is the best time to visit Kailua-Kona?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$237 AUD$272 AUD$252 AUD$237 AUD$230 AUD$216 AUD$199 AUD$197 AUD$202 AUD$216 AUD$216 AUD$231 AUD
Avg. temp6°C6°C6°C7°C9°C10°C9°C9°C9°C9°C7°C6°C

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