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Holiday rentals in Kailua-Kona

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Top-rated holiday rentals in Kailua-Kona

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

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Guest suite in Kailua-Kona

4.87 out of 5 average rating, 420 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.

23–30 Mar

$135 SGD per night

Guest favourite

Cottage in Kailua-Kona

4.95 out of 5 average rating, 347 reviews

Radiant Ocean View Cottage on a Coffee Farm. Very Private.

Centrally located between South Kohala's beaches, and the dining and entertainment scene of Kailua-Kona, the Kaloko Coffee Cottage is at a cool elevation making naps after adventures a...well a dream! Far from any roads, the dominant sounds are the many birds who make their homes in the surrounding trees. This is a thoughtfully furnished home with an open layout, on a coffee farm, just bring your food and clothes for which ever adventure you intend; leave the accommodations and ambiance to us.

17–24 Mar

$250 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.93 out of 5 average rating, 399 reviews

Ohana Suite Close to Town with A/C

This is our ohana suite in a quiet residential area. The suite includes access to your own lanai complete with patio furniture. We are 20 minutes from the international airport and less than a 10 min drive to center of downtown with restaurants and shopping areas. 7 min drive to magic sand beach and only a 15 min walk to Ali'i drive. We live on the property upstairs and you will have your own entrance. There is keyless entry via code for your convenience. A/C available.

16–23 Jul

$157 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.93 out of 5 average rating, 470 reviews

Hale Walua Ocean View Artist's Ohana

Welcome to Hale Walua. We love sharing our Ohana and aloha with fellow travelers. Your apartment has a private entrance, ocean view, gorgeous garden dining areas abundant with flowers and fruit, comfy queen bed, kitchenette, lounge room, wifi, Apple TV and full bath along with all the beach toys you'll need during your visit to Hawaii's Big Island. Beauty and peace abounds. Several world premier beaches are within a 10- 25 minute drive.

13–20 Mar

$210 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.91 out of 5 average rating, 225 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.

11–18 Oct

$162 SGD per night

Guest favourite

Guest house in Kailua-Kona

4.95 out of 5 average rating, 317 reviews

Cottage with Ocean and Sunset view

Situated on the western side of the island at a cool 1300ft elevation, this is a small cottage suitable for two people. Privacy is the key word. This is a quiet, clean, peaceful place with A/C, near the airport, town + 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!

15–22 Oct

$150 SGD per night

Guest favourite

Guest suite in Hōlualoa

4.97 out of 5 average rating, 475 reviews

Cozy apartment in Holualoa

Aloha and Mahalo for visiting my listing. "Pl.note that I don't have included the State& County Transient /Ge tax ( 17.50%) in my price since it would reflect in the fee you pay to airbnb. I will collect it upon arrival." This place is nesteld on the slope of Hualalei mountain inmidst of coffee farms, from this cooler elevation (1200ft.) it is only 15 min./7 miles to Kailua -Kona, the nearest Beaches and Supermarket.

7–14 Apr

$204 SGD per night

Guest favourite

Guest suite in Waimea

4.98 out of 5 average rating, 159 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.

30 Dec – 6 Jan

$165 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.92 out of 5 average rating, 331 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.

8–15 Aug

$192 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.97 out of 5 average rating, 143 reviews

Picturesque Private Studio / Panoramic Ocean Views

Breathtaking studio suite perched at 1100 feet elevation in a residential neighborhood of tropical one acre estates, providing privacy, expansive 180 degree ocean views and cool breezes. Enjoy the peaceful sanctuary of your private lanai for sipping your favorite beverage while gazing at the fabulous coastal views and sunsets. You will find everything you need for your vacation or business stay.

12–19 Jun

$196 SGD per night

Guest favourite

Flat in Kailua-Kona

4.95 out of 5 average rating, 428 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...

15–22 Jun

$196 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.95 out of 5 average rating, 487 reviews

Cozy, Private Studio with an Incredible View!

Just 10 minutes from Kona International Airport, this private studio is perfectly situated as the start for your Big Island adventure. The space is bright and airy with French doors that open to the lanai for an even more spacious feel. There is a closet, a private washer and dryer, basic amenities, a 65” smart TV, and USB outlets. There is a queen bed and a comfortable couch.

6–13 Mar

$201 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Houses

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Villas

Luxurious estates for the ultimate escape

Flats

Convenient locations with everyday essentials

Popular amenities for Kailua-Kona holiday rentals

Free parking on premises

Air conditioning

Stay near Kailua-Kona's top sights

Royal Kona Resort27 locals recommend

Kona Farmers Market68 locals recommend

Courtyard by Marriott King Kamehameha's Kona Beach Hotel28 locals recommend

Old Kona Airport State Recreation Area40 locals recommend

Kailua Pier19 locals recommend

Kona Inn Shopping Village16 locals recommend

Other great holiday rentals in Kailua-Kona

Guest favourite

Guest house in Kailua-Kona

4.96 out of 5 average rating, 157 reviews

Our Hawaii Hale: Detached 2 bed ohana with parking

26 Nov – 3 Dec

$194 SGD per night

Guest favourite

Flat in Kealakekua

4.93 out of 5 average rating, 380 reviews

Hale's Hale

12–19 Oct

$158 SGD per night

Guest favourite

Guest house in Holualoa

4.96 out of 5 average rating, 194 reviews

Holualoa Jungle Getaway (15 min from Kona)

13–20 Jul

$187 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.95 out of 5 average rating, 198 reviews

Walk to Magic Sands Beach! Prime Location

5–12 Jul

$189 SGD per night

Guest favourite

Guest suite in Kailua-Kona

5.0 out of 5 average rating, 246 reviews

Your Big Island Escape - King Bed & A/C

2–9 Sep

$205 SGD per night

Guest favourite

Cottage in Kealakekua

4.92 out of 5 average rating, 258 reviews

Private Cottage on coffee farm, Ocean-Sunset View

31 May – 7 Jun

$203 SGD per night

Guest favourite

Farm stay in Captain Cook

4.85 out of 5 average rating, 131 reviews

Honaunau Farm Retreat - Garden Cottage

20–27 Aug

$200 SGD per night

Guest favourite

Guest suite in Kailua-Kona

4.99 out of 5 average rating, 366 reviews

Inna’s Cottage - Modern, Tropical Getaway

4–11 Apr

$203 SGD per night

Quick stats about holiday rentals in Kailua-Kona

Total rentals
1.9K properties
Rentals with dedicated workspaces
970 properties have a dedicated workspace
Rentals with a pool
1.5K properties have a pool
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
860 properties are a good fit for families
Total number of reviews
74K reviews

Destinations to explore