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: <a href="/property/prime-oceanfront-kona-reef-vacation-condo-d-building/HA-321468043" class="class="static-page-link"">Prime Oceanfront Kona Reef Vacation Condo - D Building</a> <a href="/property/penthouse-unit-built-2007-across-from-kahaluu-beach-fantastic-ocean-views/HA-1213781525" class="class="static-page-link"">Penthouse Unit built 2007, Across from Kahaluu Beach, Fantastic Ocean Views!</a> <a href="/property/direct-oceanfront-condo-with-ac-amazing-sunsets-tide-pools-turtles-surfers/HA-1214477435" class="class="static-page-link"">Direct Oceanfront Condo with AC, Amazing Sunsets, Tide Pools, Turtles &amp; Surfers</a> <a href="/property/kona-reef-b34-beachfront-walk-to-town-air-con-wifi-top-floor/HA-1214768564" class="class="static-page-link"">Kona Reef B34/Beachfront/Walk to Town/Air Con/WiFi/Top Floor</a> <a href="/property/306-aircon-upgraded-corner-unit-w-expansive-ocean-views-and-extra-large-lanai/HA-121959190" class="class="static-page-link"">306-AirCon. Upgraded Corner Unit w/Expansive Ocean Views and Extra Large Lanai.</a> <a href="/property/oceanfront-luxury-affordable-oceanfront-condo-now-with-a-c/HA-32130790" class="class="static-page-link"">Oceanfront Luxury! - Affordable Oceanfront Condo Now with A/C!</a> <a href="/property/ahhhh-paradise-ocean-views-in-luxurious-condo-snorkeling-surfing-steps-awayn/HA-321231615" class="class="static-page-link"">Ahhhh.Paradise OCEAN VIEWS in Luxurious condo, Snorkeling,Surfing steps awayn</a> <a href="/property/oceanfront-top-floor-two-bedroom-updated-including-split-system-ac/HA-321683570" class="class="static-page-link"">Oceanfront, Top Floor, Two-Bedroom/Updated including split system AC!</a> <a href="/property/your-hawaiian-vacation-starts-here-ii/HA-321732798" class="class="static-page-link"">Your Hawaiian Vacation Starts Here! II</a> <a href="/property/special-discount-10-7nt-stay-on-this-beautiful-property/HA-321630663" class="class="static-page-link"">SPECIAL DISCOUNT 10% 7NT STAY on this beautiful property</a>

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 $634 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 on this beautiful property See all <a href="/all/usa/hawaii/kailua-kona/pet-friendly-rentals" class="class=&#34;static-page-link&#34;">pet-friendly vacation rentals in Kailua-Kona</a> 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 2489 private swimming pools or indoor pools accommodations near Kailua-Kona along with other great amenities.

Winter Rentals in Kailua-Kona:【 GREAT PRICES 】

Oceanfront Condo, 5G Wi-Fi, King Bed, Hot Tub/Pool, Free Parking

From US $381

10.0 (225 Reviews)

Condo

Oceanfront Condo, 5G Wi-Fi, King Bed, Hot Tub/Pool, Free Parking

Air Conditioner
Parking
Pool

Kailua-Kona Winter Rentals & Holiday Homes

Discover winter rentals Kailua-Kona - We found 2489 exact matches

When do you want to travel?