Kailua-Kona holiday rentals

We found 4,040 holiday rentals — enter your dates for availability

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October 2025

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If you are looking to stay near Kailua-Kona, HI (KOA-Kona Intl.), scroll through and discover holiday rentals to find the perfect one for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll have the amenities that you expect and more, such as Wi-Fi and cable TV. What you'll find is a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Kailua-Kona, HI (KOA-Kona Intl.)

Showing deals for:16 Jan - 23 Jan

Exceptional

(5 reviews)

Mauna Lani Luxury 3BR Oasis : Infinity Pool, Ocean

Kamuela, HI

11% off

for 7 nights, 1 villa

AU$3,232 per night

includes taxes & fees

Exceptional

(50 reviews)

Ultra private oceanfront gated compound with pool & spa just minutes from town.

Kailua-Kona, HI

8% off

for 7 nights, 1 villa

AU$5,833 per night

includes taxes & fees

HISTORICAL DISTRICT OF KAHALU'U. PLACE. SURF, CANOEING, AGRICULTURAL OF CHIEFS.!

Exceptional

(95 reviews)

FABULOUS BEACH HOUSE, OCEAN FRONT VIEW, BEST LOCATION, WALK TO BEACH, RELAXING!.

Kailua-Kona, HI

6% off

for 7 nights, 1 home

AU$904 per night

includes taxes & fees

Welcome to your private backyard oasis with pool and spa!

Exceptional

(61 reviews)

Private Villa, Golf Course Front with a Private Pool and Spa!

Kamuela, HI

7% off

for 7 nights, 1 home

AU$2,220 per night

includes taxes & fees

Exceptional

(97 reviews)

Enjoy Panoramic Ocean Sunset Views From Your Private, Gated Residence

Kailua-Kona, HI

10% off

for 7 nights, 1 home

AU$2,682 per night

includes taxes & fees

Coming up the gated driveway, at night...the guest house is on the left

Exceptional

(53 reviews)

Guest house on gated acre estate, Sleeps up to 7; Great for Events, too

Kailua-Kona, HI

7% off

for 7 nights, 1 home

AU$473 per night

includes taxes & fees

Exceptional

(46 reviews)

Villa On The Ocean - One Of Largest Condos On Alii Drive. Directly Oceanfront.

Kailua-Kona, HI

8% off

for 7 nights, 1 villa

AU$1,696 per night

includes taxes & fees

Exceptional

(23 reviews)

Beautiful, Updated & Lush Settings 🐠 House with Privacy, Pool & Nearby beaches🐢 Kololia Living

Kailua-Kona, HI

5% off

for 7 nights, 1 home

AU$1,260 per night

includes taxes & fees

A beautiful pool & hottub @ White Sands Village! Enjoy a swim, the sun & view!

Exceptional

(68 reviews)

Paradise! Kailua-Kona Oasis, Ocean View! Parking +AC! Steps 2 Magic Sands Beach!

Kailua-Kona, HI

7% off

for 7 nights, 1 apartment

AU$633 per night

includes taxes & fees

Exceptional

(19 reviews)

Manta Ray Manor - Oceanfront Gated Community, short walk to beach and town.

Kailua-Kona, HI

8% off

for 7 nights, 1 home

AU$2,946 per night

includes taxes & fees

Exceptional

(10 reviews)

Aloha Style! End Corner Unit w/ Ocean and Fairway Views! Kanaloa at Kona 1402

Kailua-Kona, HI

7% off

for 7 nights, 1 apartment

AU$1,040 per night

includes taxes & fees

Sunset glow from relaxing, private lanai.

Exceptional

(53 reviews)

Beach Villas at Kahalu‘u, Sunset/Ocean Views, Prime Snorkel/Surf Beach, Pool/Spa

Kailua-Kona, HI

7% off

for 7 nights, 1 apartment

AU$627 per night

includes taxes & fees

Exceptional

(158 reviews)

Delightful Artful Bungalow on Historic Estate Property. Choice Holualoa!

Holualoa, HI

7% off

for 7 nights, 1 cottage

AU$438 per night

includes taxes & fees

Exceptional

(29 reviews)

Big Price Drop! Spectacular Charming🍍Remodeled Hawaiian Home in White Sands Area🤿 Hale NaniLoa

Kailua-Kona, HI

5% off

for 7 nights, 1 home

AU$872 per night

includes taxes & fees

Exceptional

(25 reviews)

Gated Community Located Within Walking Distance To The Beach

Kailua-Kona, HI

7% off

for 7 nights, 1 home

AU$700 per night

includes taxes & fees

Exceptional

(93 reviews)

Mauna Lani-Luxurious, Private beach club pass, Lanai sunsets, closest to ocean

Kamuela, HI

7% off

for 7 nights, 1 apartment

AU$947 per night

includes taxes & fees

Oceanfront views from your beautiful oceanfront lanai!

Exceptional

(86 reviews)

Amazing 🏄‍♀️ Oceanfront Penthouse 🐬 Newly Renovated! - Banyan Tree 403C 🌅

Kailua-Kona, HI

5% off

for 7 nights, 1 apartment

AU$1,068 per night

includes taxes & fees

Absolute oceanfront almost hangs over the ocean.

Wonderful

(43 reviews)

Amazing Oceanfront Condo 🐠 with Out of this World Ocean Views! 🌅 - Hale Kona Kai 203

Kailua-Kona, HI

5% off

for 7 nights, 1 apartment

AU$611 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Kailua-Kona

Enjoy your own private resort at Kaiminani.

Premier Host

Beautiful Pool with Stunning Ocean and Sunset Views

Sleeps 10 · 4 bedrooms · 3 bathrooms

Spacious "Great Room" So much light it's almost like being outside!

Premier Host

Spacious, Luxurious, Tropical Townhouse Style Condo For A Truly Aloha Vacation

Sleeps 6 · 2 bedrooms · 2+ bathrooms

Top rated rentals - Kailua-Kona

Premier Host

Great stay

Great location and property, we will be back! Thanks for having us :)

Marion M.

Stayed Oct 2024

Premier Host

Didn’t want to leave

This property is fantastic. The kitchen is well stocked, the water equipment eg snorkels greatly appreciated. 40 mins drive from Kona so it is well and truly far from the crowds. The beach is lovely and a pleasant stroll past fishponds. Access to restaurants at Mauna Lani and “The Shops” is great. The golf course was also beautifully presented and very enjoyable to play. (North) . Sitting on the Lani, enjoying the beautiful gardens and fishpond with ocean in the background so relaxing. Would love to return here

Liz W.

Stayed June 2023

Premier Host

Waaaaaay Above and Beyond!

Gale and her property a absolutely beautiful. Home made banana bread and anything else you could want in a rental are all provided with Gale’s special touch. Simply cannot rate this beautiful boutique property highly enough. 100% recommend to anyway wanting a fantastic hideaway home!

Tanya J.

Stayed Dec 2022

Premier Host

Thoroughly enjoyed our stay, very clean and tidy. Highlight was listening to the waves.

Waking up with ocean views while eating breakfast on the balcony was definitely our highlight. This place is well equipped with all of the cooking/utensils needed to enjoy a homely stay.

Jack R.

Stayed Oct 2022

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