Kaunakakai Winter Rentals & Holiday Homes
Discover winter rentals Kaunakakai - We found 49 exact matches
About Kaunakakai Winter Rental on Big Island Hawaii Rental
Planning on a winter vacation in Kaunakakai? Discover 49 places to stay in Kaunakakai, 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 Kaunakakai, 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.
Kaunakakai winter accommodation starts at US $673, and the most popular properties in Kaunakakai 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 Kaunakakai, 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 Kaunakakai and unlock even more amazing deals.
Frequently Asked Questions About Kaunakakai Winter Rental
What are the top rated Winter Rentals in Kaunakakai?
There are a lot of options in Kaunakakai. If you plan on staying in the Kaunakakai area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Kaunakakai:
- Oceanfront-Tropically Furnished Condo-Comfy
- Oceanfront Top Floor Molokai Condo! Lush East End Location!
- 2BD Peace & Paradise MOLOKAI-1.5 bath/2 LANAIS w/Oceanview-Grandeur & Gorgeous!
- Oceanfront, Breathtaking View! Summer Getaway Special! Wavecrest Resort!
- Tropical studio in oceanfront resort w/pool, WiFi, & kitchenette - snowbirds OK
- Centrally-Located Studio w/Free WiFi, Shared Pool, Grills, & Kitchenette
- Terrific Condo w/Free WiFi, Shared Pool, Tennis Court, Water Views, Shared W/D
- Amazing waterfront condo with ocean views, shared pool, balcony, & grill
- Oceanfront Molokai Shores Condo w/Pool Access!
- Charming 1st floor oceanfront condo with shared pool, tennis courts & W/D
How much does it cost to rent a place to stay near Kaunakakai in the wintertime?
The average cost for winter rentals in Kaunakakai is $673 per night. Bigislandhawaiirental has a wide list of great winter places to stay near Kaunakakai that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Kaunakakai that allow pets?
Yes, here are the top cottage/chalet rentals in Kaunakakai that allow you to bring your pet or dog:
- ‘Aloha Kai’ Oceanfront on Molokai, Top Floor, Modern, Peaceful Comfort, Pool
- Kaunakakai Vacation Rental w/Pool Access & A/C!
- Historical lodge at Pu'u O Hoku Ranch! Outdoor pool and farm-to-table meals!
- Modern Oceanfront W/Lanai and WiFi–Molokai Shores
See all pet-friendly vacation rentals in Kaunakakai on Bigislandhawaiirental
Do you have any winter rentals in Kaunakakai that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Kaunakakai to find what works for you.
Are there winter accommodations in Kaunakakai that have indoor swimming pools?
As of 2026, the data from Bigislandhawaiirental shows that there are over 49 private swimming pools or indoor pools accommodations near Kaunakakai along with other great amenities.
