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Kailua-Kona Winter Rentals & Holiday Homes
Discover winter rentals Kailua-Kona - We found 2837 exact matches
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About Kailua-Kona Winter Rental on Big Island Hawaii Rental
Planning on a winter vacation in Kailua-Kona? Discover 2837 places to stay in Kailua-Kona, for those traveling with their family, friends, in groups, or for a wedding retreat.
At Big Island Hawaii Rental, we have a wide range of listings for accommodations in Kailua-Kona, HI that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. Big Island Hawaii Rental winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Kailua-Kona winter accommodation starts at US $640, and the most popular properties in Kailua-Kona are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, Big Island Hawaii Rental will make your winter trip memorable.
Big Island Hawaii Rental offers a great deal for travelers planning on renting a place in Kailua-Kona, to enjoy these benefits and to book your winter vacation homes, go to Big Island Hawaii Rental filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Kailua-Kona and unlock even more amazing deals.
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:
- Penthouse Unit built 2007, Across from Kahaluu Beach, Fantastic Ocean Views!
- Ahhh PARADISE! Top Ocean Views, Snorkel Surf FREE Nt. w/10 day booking in Dec.
- Exotic Kona Bay Hawaii Beachfront Tropical Paradise Stunning Home.
- The “Promise Tree” is a great family gathering place in Kailua Kona!
- Oceanfront Luxury House, Pool & AC, Near Magic Sands
- This is the spa for your soul
- Hale Hina ~ Private, Peaceful, Perfection!
- 1 Mi to Magic Sands: Waterfront Big Island Condo
- Fabulous Top Floor Penthouse with Two Bedroom Suites - Unit 413
- Oceanfront Kona Condo | Watch Whales & Sunsets from Your Private Lanai
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 $640 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
- Sunset Hale: Spectacular Oceanview Home w/Private Pool & Spa, AC & Lanai
- Oceanfront Penthouse, As Close As You Can Stay To Ocean, Stunning Views, A/C!
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 2837 private swimming pools or indoor pools accommodations near Kailua-Kona along with other great amenities.
