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Holiday rentals in Kailua-Kona

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Top-rated holiday rentals in Kailua-Kona

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Guest suite in Kailua-Kona

4.86 out of 5 average rating, 454 reviews

Hibiscus; Private hotel style apartment, CLEAN

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 Hibiscus, it is set up like a hotel room; spacious room with King sized bed, large bright bathroom, lots of closet space, TV, desk and a tea/coffee station with mini fridge and microwave. THIS UNIT DOES NOT HAVE A FULL KITCHEN. Close to the airport with automated check in and flexible booking, free parking, King sized bed and large bathroom.

Treehouse in Kailua-Kona

4.88 out of 5 average rating, 331 reviews

Kona Luxury Treehouse w/Hot tub, Sauna, Ocean view

Welcome to Kona Luxury Treehouse on the Big Island! Voted the #1 airbnb in Hawaii. Experience this magical and beautifully handcrafted treehouse, nestled high above the lush 3 acres of our beautiful fruit farm. With live tree trunks grow through the center of this unique structure, JUST ADDED infrared sauna, outdoor shower, and hot tub! The treehouse boasts gorgeous views of the ocean and tropical foliage. At an elevation of 1,800 ft, our indoor/outdoor living spaces are comfortable year round.

Guest favourite

Guest suite in Kealakekua

4.95 out of 5 average rating, 379 reviews

Kona Sunset Ohana

- Exceptional location just steps away from adventure & exploring - Two new queen mattresses (bedroom and living room sleeper sofa) - Large, private, and covered outdoor living area surrounded with lush plant life - Own backyard area - Lots of seating options including couches, hammock, chairs & a pew - Private, with only shared space being the parking area - Cleaned to a high standard - Amazing sunsets viewable throughout property - Cool elevation at 1400' provides comfortable nights

Guest favourite

Guest house in Holualoa

4.95 out of 5 average rating, 102 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 favourite

Guest house in Kailua-Kona

4.96 out of 5 average rating, 559 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

Rental unit in Kealakekua

4.93 out of 5 average rating, 398 reviews

Hale's Hale

This one-bedroom apartment with an ocean view is the perfect space for you to relax and unwind after a day of fun! It has it’s own private entry and includes a queen bed, a sofa bed, a fridge, a microwave, a cooktop, A shared washer/dryer and BBQ grill! Our home sits at a cool 1300' elevation with stunning sunsets. For our fellow adventurers, It’s only 10 minutes from Keauhou Bay, 15 minutes from Kona town to the North or 2 Step snorkeling to the South.

Guest favourite

Guest suite in Kailua-Kona

4.88 out of 5 average rating, 253 reviews

MODERN space, MINUTES from beaches and airport!

Welcome to the Surf Hale! Our newly renovated, one bedroom Ohana sits at a 1500 ft. elevation along Hualalai, just a short 15 minute drive from downtown Kona. We are just minutes from the airport as well as some of the most pristine beaches on Hawai'i Island. Here you get to experience Hawaii away from the hustle and bustle of resorts and overcrowded condominiums and stay where the locals live! Our neighborhood is green, tropical, and beautiful!

Guest favourite

Guest suite in Kailua-Kona

4.88 out of 5 average rating, 252 reviews

Cozy ohana, close to airport

Aloha, welcome to my cozy ohana! Located just minutes away from the airport and some of our most beautiful beaches. It has 1 queen bed plus a couch for a 3rd person. 2 walk-in closets. Kitchen and bathroom are brand new! Kitchen includes full fridge, microwave, toaster oven, and hot plate. There's free wifi and a smart TV so you can watch your own Netflix, hulu, e.t.c. Private entrance and oh yeah, the best part...AC! Taxes included.

Guest favourite

Guest house in Kailua-Kona

4.95 out of 5 average rating, 331 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

Guest suite in Waimea

4.98 out of 5 average rating, 182 reviews

Artist designed suite. Private garden & waterfall.

Stunning guest suite, in the Parker Ranch area, 5 minutes from historic Waimea Town. Great attention to detail in this recently built, spacious, light unit with 16 foot high ceiling, skylight, local hardwood woodwork details and Carrera marble counters in kitchenette and designer bathroom. Enjoy views of Mauna Kea while relaxing on the covered lanai overlooking your private, enclosed tropical garden.

Guest favourite

Guest suite in Kailua-Kona

4.92 out of 5 average rating, 345 reviews

Honu Hale

Come enjoy our beautiful Ohana! Ideal for couples and solo adventurers alike. The location of our place allows you to conveniently enjoy the many restaurants and quaint shops of central Kailua-Kona. While it is close enough to snorkel, surf, sunbathe, or stroll along the famed and stunning beaches of Ali’i Drive, it is tucked just far enough away to enjoy the intimacy of a quiet and cozy island escape.

Guest favourite

Rental unit in Kailua-Kona

4.95 out of 5 average rating, 445 reviews

"Harbor View Hale" Romantic Retreat

Aloha! Retreat in a romantically-luxurious and renovated 1 Bedroom apt with teak canopy CAL KING bed, stainless steel appliances, washer/dryer, a lanai that overlooks the ocean with view on our lush garden with fruit trees, plants, tropical birds. We feature an in-rental TABLET to provide cutting edge support for your most extraordinary vacation experience. Property Guide, Concierge, etc...

Holiday rentals for every style

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Popular amenities for Kailua-Kona holiday rentals

Free parking on premises

Air conditioning

Stay near Kailua-Kona's top sights

Kona Brewing Company226 locals recommend

Island Lava Java163 locals recommend

Huggo's162 locals recommend

KTA Super Stores156 locals recommend

Umekes Fish Market Bar & Grill154 locals recommend

Costco Wholesale153 locals recommend

Other great holiday rentals in Kailua-Kona

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Guest suite in Kailua-Kona

5 out of 5 average rating, 277 reviews

Your Big Island Escape - King Bed & A/C

Guest favourite

Guest house in Kailua

4.92 out of 5 average rating, 402 reviews

A Piece of Paradise with Ocean Views in Kona

Guest favourite

Guest suite in Kailua-Kona

4.98 out of 5 average rating, 104 reviews

Good Vibes Ohana

Guest favourite

Home in Kailua-Kona

4.98 out of 5 average rating, 121 reviews

Knox Dojo - Full House 2b/2b

Guest suite in Kailua-Kona

4.8 out of 5 average rating, 215 reviews

Kona Jr Suite w/ ocean view - Private Entrance

Guest suite in Kailua-Kona

4.9 out of 5 average rating, 113 reviews

Cozy studio w/ full kitchen, W/D; close to town

Guest favourite

Guest suite in Waikoloa Village

4.86 out of 5 average rating, 410 reviews

Design for relax in the Paradise with A/C

Guest favourite

Rental unit in Kailua-Kona

4.88 out of 5 average rating, 216 reviews

Tropical garden apartment

Quick stats about holiday rentals in Kailua-Kona

Total rentals
1.9K properties
Total number of reviews
77K reviews
Family-friendly rentals
900 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
1.6K properties have a pool
Rentals with dedicated workspaces
1K properties have a dedicated workspace

Destinations to explore