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Vacation rentals in Kailua-Kona

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Travel insights for vacation rentals in Kailua-Kona

Use these up-to-date, data-driven insights about booking a vacation rental in Kailua-Kona including ideal times to book, pricing trends, and more.

What is the cheapest month to book a vacation rental in Kailua-Kona?

The cheapest month to book a vacation rental in Kailua-Kona is October (C$ 332). Conversely, the most expensive month to stay in Kailua-Kona is December (C$ 691).

What is the cheapest day to stay in a vacation rental in Kailua-Kona?

The cheapest day to stay in Kailua-Kona is Tuesday (C$ 368). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is C$ 742.

How far ahead should you book a vacation rental in Kailua-Kona?

Save money by booking a vacation rental at least 76 days before your trip to Kailua-Kona. The lowest price found when booking 76 days ahead was C$ 258 per night.

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Cheapest vacation rentals in Kailua-Kona, Hawaii

Discover affordable stays in Kailua-Kona that provide a quality experience without breaking the bank. Hotels in Kailua-Kona can be found for as low as C$ 234 per night. There is currently one property in Kailua-Kona that can be booked for this price. Bears' Place Guest House is one of the hotels that can be booked for the lowest price in Kailua-Kona. Price data was last updated on 7 January 2026
Currently, these are the lowest-priced vacation rentals in Kailua-Kona we've come across for the dates selected. If you have the flexibility, change the dates selected to compare prices.
Bears' Place Guest House
Bears' Place Guest House

Bears' Place Guest House

Kailua-Kona, The Big Island, HI, United States
11.1 km from city centre
C$ 234
Avg. per night
View Deal
Castle at Kona Reef
Castle at Kona Reef

Castle at Kona Reef

Kailua-Kona, The Big Island, HI, United States
1.1 km from city centre
Air Conditioning
C$ 314
Avg. per night
View Deal
Kona Islander Inn Condos
Kona Islander Inn Condos

Kona Islander Inn Condos

75-5776 Kuakini Highway, Kailua-Kona, The Big Island, HI, United States
0.3 km from city centre
Free Wi-Fi
Parking
C$ 341
Avg. per night
View Deal
Hale Kona Kai by Casago Kona
Hale Kona Kai by Casago Kona

Hale Kona Kai by Casago Kona

Kailua-Kona, The Big Island, HI, United States
1.0 km from city centre
Air Conditioning
Free Wi-Fi
C$ 417
Avg. per night
View Deal
Raintree's Kona Reef
Raintree's Kona Reef

Raintree's Kona Reef

Kailua-Kona, The Big Island, HI, United States
1.1 km from city centre
Air Conditioning
C$ 427
Avg. per night
View Deal
Kanaloa At Kona By Outrigger
Kanaloa At Kona By Outrigger

Kanaloa At Kona By Outrigger

Kailua-Kona, The Big Island, HI, United States
8.7 km from city centre
Air Conditioning
C$ 427
Avg. per night
View Deal

Other accommodations in Kailua-Kona

Find the perfect vacation rental for your stay in Kailua-Kona. There are 2,242 hotels in Kailua-Kona and price data was last updated on 7 January 2026. The average price for a hotel in Kailua-Kona is C$ 474/night.
Mango Sunset Bed and Breakfast
Mango Sunset Bed and Breakfast

Mango Sunset Bed and Breakfast

73-4261 Hawaii Belt Rd, Kailua-Kona, The Big Island, HI, United States
9.5 km from city centre
Free Wi-Fi
C$ 433
Avg. per night
View Deal
Kanaloa At Kona By Outrigger
Kanaloa At Kona By Outrigger

Kanaloa At Kona By Outrigger

Kailua-Kona, The Big Island, HI, United States
8.7 km from city centre
Air Conditioning
C$ 427
Avg. per night
View Deal
Four Seasons Resort Hualalai
Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

72-100 Ka'Upulehu Drive, Kailua-Kona, The Big Island, HI, United States
20.9 km from city centre
Free Wi-Fi
C$ 2,098
Avg. per night
View Deal
Sea Village
Sea Village

Sea Village

75-5992 Alii Drive, Kailua-Kona, The Big Island, HI, United States
1.9 km from city centre
Free Wi-Fi
Parking
C$ 367
Avg. per night
View Deal
Mauna Lani, Auberge Collection
Mauna Lani, Auberge Collection

Mauna Lani, Auberge Collection

68-1400 Mauna Lani Drive, Kailua-Kona, The Big Island, HI, United States
36.5 km from city centre
C$ 1,070
Avg. per night
View Deal
Hale Maluhia Country Inn
Hale Maluhia Country Inn

Hale Maluhia Country Inn

76-770 Hualalai Road, Kailua-Kona, The Big Island, HI, United States
3.9 km from city centre
Free Wi-Fi
Air Conditioning
Spa
C$ 339
Avg. per night
View Deal
Holualoa Inn
Holualoa Inn

Holualoa Inn

76-5932 Mamalahoa Highway, Kailua-Kona, The Big Island, HI, United States
4.7 km from city centre
Free Wi-Fi
C$ 1,077
Avg. per night
View Deal

Where to stay in Kailua-Kona

Explore different neighbourhoods and areas within Kailua-Kona to find the perfect location for your stay. Map data was last updated on 7 January 2026.
Scroll to and zoom in on the areas in Kailua-Kona you plan on visiting to find nearby properties. Clicking a property's name will unlock more information and allow you to book that particular vacation rental.

Facts about staying in Kailua-Kona

Find useful tips and insights about staying in Kailua-Kona to help you make the most of your experience. FAQs were last updated on 7 January 2026.

  • How much does a vacation rental in Kailua-Kona cost?

    Kailua-Kona vacation rentals are C$ 475/night on average. However, you may find that prices fluctuate depending on the time of year. For example, December is the most expensive month to book a vacation rental in Kailua-Kona, and February is often the cheapest month to book. Recently, our users found rentals for C$ 47/night - which is currently the cheapest price. Keep in mind that anything C$ 347/night or less is still considered a good deal.

  • What’s the closest vacation rental to Kona Intl Airport?

    It’s only 6.8 km from Kona Intl Airport to Bears' Place Guest House (the nearest Kailua-Kona vacation rental to the airport).

  • Are there Kailua-Kona vacation rentals with “Air-conditioned” listed as an amenity?

    You’re in luck! 2 Kailua-Kona vacation rentals mention “Air-conditioned” under their list of amenities. The Bears' Place Guest House is the most popular vacation rental in Kailua-Kona that features this amenity.

  • Are there any Resort vacation rentals in Kailua-Kona?

    Yes, there are 32 Resort vacation rentals in Kailua-Kona. According to our data, Royal Kona Resort is currently the most popular Resort rental in the city.

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