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Vacation rentals in Kailua-Kona

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Travel insights for holiday rentals in Kailua-Kona

Use these up-to-date, data-driven insights about booking a holiday 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 January (S$ 278). Conversely, the most expensive month to stay in Kailua-Kona is September (S$ 1,268).

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

The cheapest day to stay in Kailua-Kona is Monday (S$ 286). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is S$ 619.

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 S$ 233 per night.

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Cheapest holiday 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 S$ 196 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 14 March 2026
These Kailua-Kona properties charge the lowest price per night of those we've come across. As prices can vary by date, change the dates if you're flexible to compare rates.
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
S$ 196
Avg. per night
View Deal
Vacation Condos In Kona
Vacation Condos In Kona

Vacation Condos In Kona

75-5776 Kuakini Highway, Kailua-Kona, The Big Island, HI, United States
0.3 km from city centre
Air conditioning
S$ 285
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
S$ 302
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
S$ 358
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
S$ 362
Avg. per night
View Deal

Other accommodations in Kailua-Kona

Find the perfect holiday rental for your stay in Kailua-Kona. There are 2,273 hotels in Kailua-Kona and price data was last updated on 14 March 2026. The average price for a hotel in Kailua-Kona is S$ 476/night.
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
S$ 196
Avg. per night
View Deal
Aston Kona By The Sea
Aston Kona By The Sea

Aston Kona By The Sea

75-6106 Alii Drive, Kailua-Kona, The Big Island, HI, United States
2.8 km from city centre
S$ 383
Avg. per night
View Deal
Pacific 19 Kona
Pacific 19 Kona

Pacific 19 Kona

75-5646 Palani Road, Kailua-Kona, The Big Island, HI, United States
0.7 km from city centre
Free Wi-Fi
S$ 243
Avg. per night
View Deal
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
S$ 357
Avg. per night
View Deal
Big Island Retreat - No Resort Fees
Big Island Retreat - No Resort Fees

Big Island Retreat - No Resort Fees

78-226 Kahaluu Road, Kailua-Kona, The Big Island, HI, United States
7.0 km from city centre
Free Wi-Fi
Parking
S$ 221
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
S$ 1,757
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
S$ 324
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
S$ 775
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
S$ 358
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 14 March 2026.
Use the map to find vacation rentals in Kailua-Kona that are close to the points of interest you'll be frequenting. Users can click on a vacation rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

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 14 March 2026.

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

    On average, it costs S$ 476 per night for a Kailua-Kona holiday rental, but S$ 299 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Kailua-Kona was for S$ 81 per night. If you can, try to avoid booking your rental September (as this is the most expensive month). Booking October (the cheapest month) may end up saving you money.

  • What is the best Kailua-Kona holiday rental?

    While there may be other great holiday rentals in Kailua-Kona to choose from, Royal Sea Cliff Kona by Outrigger is currently considered the best, based on 290 HotelsCombined reviews and an average rating of 8.0/10.

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

    If you’re looking to stay close to Kona Intl Airport for your trip to Kailua-Kona, then consider booking a Royal Sea Cliff Kona by Outrigger holiday rental. This holiday apartment is just 14.7 km away from the Kailua-Kona airport.

  • Are there Kailua-Kona holiday rentals with “Pool” listed as an amenity?

    Yes, Kailua-Kona has 1 holiday rental with “Pool” listed as an amenity. Based on HotelsCombined data, the Royal Sea Cliff Kona by Outrigger is the most popular rental in Kailua-Kona with this amenity.

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

    There are 32 holiday rentals in Kailua-Kona that fall under the Resort category, the most popular is Royal Kona Resort.

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