Kailua-Kona Winter Rentals & Holiday Homes

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!

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.

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

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.

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.