Paia Winter Rentals & Holiday Homes

The average cost for winter rentals in Paia is $681 per night. Pacificislands has a wide list of great winter places to stay near Paia 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 Paia that allow you to bring your pet or dog:

• Charming. permitted cottage, short walk to Paia town & beach.nSTPH 2013/0004
• King Room-Mangolani Inn
• Maui North Shore Villa: Private Pool, Courtyard & Steps to Baby Beach
• Gingerbread House-Less than a mile from Paia town and all North Shore beaches

See all pet-friendly vacation rentals in Paia on Pacificislands

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Paia to find what works for you.

As of 2026, the data from Pacificislands shows that there are over 20 private swimming pools or indoor pools accommodations near Paia along with other great amenities.

About 20 holiday rentals in Paia boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

• Paia Rentals with hot tub