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.
Our favorite places to stay in Kailua-Kona, Hōlualoa, and Kealakekua.
We have compiled a small list with vacation rentals close to downtown Kailua-Kona below 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 note 1 to compare (far) more options.
Ocean view condo in downtown Kailua-Kona:
Fully-equipped 1 bedroom condo in downtown Kailua-Kona with a spacious balcony that overlooks the ocean. Located in the heart of old Kailua town at 600 m of Magic Sands Beach it includes access to an outdoor swimming pool, free private parking, and a BBQ [read more here].
A comfortable balcony view great views of the ocean and the sunset.
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 [read more here].
Overview of the upper lawn adjacent to the pool, hot tub, and lanai – all overlooking the ocean. Image credit: Kona Heavens Hideaway
Cozy and affordable apartment in Hōlualoa
A cozy apartment (4 people max) in Hōlualoa 500 meters from the Keahou shopping center and within 2 miles from some of the most popular beaches in the area. Facilities include are free private parking, an outdoor pool and a BBQ area [read more here].
This mountain cabin in the Kaloko cloud forests above Kailua Kona
7 miles from Kailua Kona but seemingly a world away, this cozy mountain cabin is located on a 5-acre property right next to the cloud forests of the Honua‘ula Forest Reserve. It comes with a secluded hot tub, yard and large lanai perfect for the bbq and is best-suited for 2-3 adults [read more here].
At 7 miles from Kona, this private chalet is set on 5 acres of trees filled with native birds.
Kealakekua Bay B&B with Gorgeous view
Technically a Bed and Breakfast but to good not to show in this list.
The Kaʻawaloa B&B is a start-up coffee and tropical fruit farm located in the heart of the Kona Coffee Belt directly above Kealakekua Bay that gets exceptional reviews from their guests. Their 5-acre terrain is at an elevation of 1,200 feet above sea level making it wonderfully cool in the evenings and giving it great ocean views [read more here].
Evening view from the back Lanai of the Kaʻawa Loa Guesthouse.
Just saying: Kealakekua Bay is one of our favorite places to explore on the Big Island ;)
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.
[1] We are part of the Vrbo and Booking 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]