Kaunakakai Winter Rentals & Holiday Homes

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!
• Spectacular, 180 Degree, Oceanfront View! Wavecrest Resort. Private Internet!
• 2BD Peace & Paradise MOLOKAI-1.5 bath/2 LANAIS w/Oceanview-Grandeur & Gorgeous!
• Terrific Condo w/Free WiFi, Shared Pool, Tennis Court, Water Views, Shared W/D
• Amazing waterfront condo with ocean views, shared pool, balcony, & grill
• Pu'u O Hoku” is true to its Hawaiian name — which means “Hill of Stars”— surrounded by more than 14,000 acres of protected land, immersed in the transcendent beauty of forest, sky, and ocean. The Ranch is a family-owned biodynamic and organic ranch a
• Pool Access: Ocean-View Molokai Shores Condo!
• Charming 1st floor oceanfront condo with shared pool, tennis courts & W/D
• Oceanfront Molokai Shores Condo w/Pool Access!

The average cost for winter rentals in Kaunakakai is $653 per night. Pacificislands 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.

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
• Coastal Kaunakakai Condo with Ocean-View Balcony!
• 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 Pacificislands

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.

As of 2026, the data from Pacificislands shows that there are over 49 private swimming pools or indoor pools accommodations near Kaunakakai along with other great amenities.