There are over 1000 vacation rentals in and near Kailua Kona available through several booking websites, and we recommend that you use whatever platform you are comfortable with to find them. While searching try to narrow your search down by providing your travel dates, and by sorting on either “price” or “traveler rating”.
If you find multiple favorite places a good strategy is to read individual reviews, and especially the bad ones! Not everyone has the same standards and seeing what people did or didn’t like, and how the owners respond to such feedback, can give you important clues on how you will like your stay.
List of Vacation Rentals in Kailua-Kona (including Hōlualoa and Kealakekua)
We have compiled a small list with vacation rentals close to downtown Kailua-Kona below (all listed on the AirBnB note 1 website) to get your search started. Most of these houses are in high demand and of them may already be booked for the dates of your stay, but they will give you an idea of what is possible for your stay.
You can also see the Kailua Kona vacation rentals listed on the Booking.com website to compare your options.
Condo in downtown Kailua-Kona:
Beautiful Condo in downtown Kailua-Kona (1 bedroom / 2 beds). This condo is located in the heart of old Kailua town at only minutes away from Kailua bay. It includes access to a saltwater pool and a rooftop for BBQ. [listing]
Overlooking Kailua-Kona, with private pool and amazing coastline views
This 2 bedroom (5 guests max) house with a private pool is located on a one-acre estate, where you can help yourself to the fruit on the trees, the herbs in the gardens, and the hammock under the trees. Close to downtown Kona and the west coast beaches but at a 900 ft. elevation, you are exposed to the cooling trade winds and the best sunsets on the island. [listing]
Cozy apartment in Hōlualoa
A Cozy apartment in Hōlualoa in the middle of coffee farms (1 bedroom / 1 bed / 2 guests). Hōlualoa is a quaint small town 15 minutes / 7 miles above Kailua-Kona. Its elevation (1200 ft.) makes it pleasantly cool. [listing]
Private residence + hot tub on 3-acre coffee farm in Hōlualoa
Located less than 10 minutes by car from Kailua-Kona on the cooler slopes of the Hualalai volcano. The owner lives on the coffee farm and can give farm tours and loves to talk about coffee farming! [listing]
Kealakekua Bay Cottage with Gorgeous view
This is a small (1 bedroom / 1 bed / 2 guests) private cottage with a cute garden and mesmerizing views over Kealakekua bay and in the middle of the lush and tropical Kona Coffee country. [listing].
For the record: Kealakekua Bay is one of our favorite places to explore on the Big Island!
AirBnB Plus homes (Kona / South Kona / Waikoloa):
These homes are a selection of the highest quality homes on AirBnB with hosts known for great reviews and attention to detail. Every home is verified through in-person quality inspection to ensure quality and design.
Not be the most affordable choices (although some are), but all homes that made it into this list are spectacular! [listings]
Things to consider when choosing a Vacation Rental:
Vacation rentals have become the accommodation of choice for many visitors over the recent years and egal frameworks are now being worked on to make sure that owed taxes are payed and that the surrounding communities also benefit. To make sure you choose accommodations that pay their taxes and are legal you should pay attention to the following things:
- Always look for a Transient Accommodation Tax (TAT) number or TAT ID on the listing. Only listings which pay their TAT are legal and pay taxes.
- Starting September 2019 most vacation rentals on the Big Island should be in the possession of a “Non conforming use certificate”, only vacation rentals properties that are localized in a Resort zone do not need to obtain such a certificate.
Do you like VRBO over AirBnB?
If you are more used to using VRBO and want to help support the Love Big Island website we’d like to ask you to search using the following URL: Vrbo. Booking through our website means we’ll get a small kickback without extra costs to you [see note 1]. Mahalo!
 We are part of the Vrbo and AirBnB affiliates program. This means we receive a small fee for every completed booking we send their way. This money comes out of their advertising budget, and it does not cost you anything extra. Read more about our participation or [go back up]