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Kailua-Kona Winter Rentals & Holiday Homes
Discover winter rentals Kailua-Kona - We found 2498 exact matches
When do you want to travel?
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Frequently Asked Questions About Kailua-Kona Winter Rental
What are the top rated Winter Rentals in Kailua-Kona?
There are a lot of options in Kailua-Kona. If you plan on staying in the Kailua-Kona area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Kailua-Kona:
- Prime Oceanfront Kona Reef Vacation Condo - D Building
- Penthouse Unit built 2007, Across from Kahaluu Beach, Fantastic Ocean Views!
- Direct Oceanfront Condo with AC, Amazing Sunsets, Tide Pools, Turtles & Surfers
- Kona Reef B34/Beachfront/Walk to Town/Air Con/WiFi/Top Floor
- 306-AirCon. Upgraded Corner Unit w/Expansive Ocean Views and Extra Large Lanai.
- Oceanfront Luxury! - Affordable Oceanfront Condo Now with A/C!
- Ahhhh.Paradise OCEAN VIEWS in Luxurious condo, Snorkeling,Surfing steps awayn
- Your Hawaiian Vacation Starts Here! II
- Kitchen and Bath Remodel! - Ocean Front - Central Air - Featured on Today Show
- Oceanfront, Top Floor, Two-Bedroom/Updated including split system AC!
How much does it cost to rent a place to stay near Kailua-Kona in the wintertime?
The average cost for winter rentals in Kailua-Kona is $627 per night. Bigislandhawaiirental has a wide list of great winter places to stay near Kailua-Kona that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Kailua-Kona that allow pets?
Yes, here are the top cottage/chalet rentals in Kailua-Kona that allow you to bring your pet or dog:
- Oceanfront Condo, 5G Wi-Fi, King Bed, Hot Tub/Pool, Free Parking
- Carson's Kaloko Mountain Cabin
- Na Hale O Keauhou Beach Views, Hot Tub & Pool
- SPECIAL DISCOUNT 10% 7nt STAY MARCH SPECIAL 9-18 ask for additional 10%
See all pet-friendly vacation rentals in Kailua-Kona on Bigislandhawaiirental
Do you have any winter rentals in Kailua-Kona that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Kailua-Kona to find what works for you.
Are there winter accommodations in Kailua-Kona that have indoor swimming pools?
As of 2026, the data from Bigislandhawaiirental shows that there are over 2498 private swimming pools or indoor pools accommodations near Kailua-Kona along with other great amenities.