Anahola Winter Rentals & Holiday Homes

There are a lot of options in Anahola. If you plan on staying in the Anahola area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Anahola:

• Sweet Rustic Cottage ~ Ocean View ~ Short walk to beach
• AT THE SHORE ON ALIOMANU BAY-TVNC-1127
• Large Gated Oceanfront Estate ~ Secluded on a beach, safe all year TVNC-4185
• Peaceful Paradise
• Sweet Country Cottage
• Kauai Explorer Camp with Rooftop Tent Adventure Comfort Gear-Included
• Kauai Rooftop Camper Truck Full Camping Gear Beach Setup
• Kauai Explorer Camper Drive, Camp & Relax with All Gear Included
• Island Breeze Camper Coastal Glamping with Full Gear Included
• Luxe Beachfront Anahola with A/C

The average cost for winter rentals in Anahola is $1,431 per night. Pacificislands has a wide list of great winter places to stay near Anahola 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 Anahola that allow you to bring your pet or dog:

• Hale Makai Beachfront Home, AC, Oceanfront on Anahola Bay, TVNC# 5065
• Sandcastles TVNC#1305
• Gated Beachfront Estate - On the Sand -Secluded Beach safe year round TVNC-4245
• Anahola Aloha Beach House home
• Luxe Beachfront Anahola with A/C
• Anahola Beach House 6br
• Rooftop Camper Experience Fully Equip
• Large Gated Oceanfront Estate ~ Secluded on a beach, safe all year TVNC-4185

See all pet-friendly vacation rentals in Anahola on Pacificislands

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

As of 2026, the data from Pacificislands shows that there are over 11 private swimming pools or indoor pools accommodations near Anahola along with other great amenities.