1. Hawaii
  2. Oahu
  3. Winter Rental

Oahu Winter Rentals & Holiday Homes

Discover winter rentals Oahu - We found 6067 exact matches

About Oahu Winter Rental on Hawaii.Villas

Planning a winter vacation in Oahu? Discover 6067 places to stay, ideal for family trips, group getaways, or wedding retreats.

At HawaiiVillas, explore a wide range of accommodations in Oahu, HI perfect for your winter escape. Our listings feature private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, all equipped with top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winter accommodations in Oahu start at US $635, with popular options including cabins, bungalows, and privately owned rental homes. Planning a snowboarding adventure? We offer numerous snowboard-friendly ski resorts, chalets, and cabins available for short-term or extended stays, whether for a weekend getaway or a longer retreat.

HawaiiVillas provides great deals for travelers seeking rentals in Oahu. To secure your winter vacation home, visit HawaiiVillas, use our filter options to specify your travel dates, property type, and desired amenities. Choose from a comprehensive list of winter vacation rentals hassle-free. Explore our interactive map to discover all lodging options in and around Oahu and unlock exclusive deals.

Show more
Show less

Winter Rental: Explore Top Destinations

Explore More

Frequently Asked Questions About Oahu Winter Rentals

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

The average cost for winter rentals in Oahu is $635 per night. Hawaii.Villas has a wide list of great winter places to stay near Oahu 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 Oahu that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Oahu on Hawaii.Villas

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Oahu to find what works for you.
As of 2026, the data from Hawaii.Villas shows that there are over 6067 private swimming pools or indoor pools accommodations near Oahu along with other great amenities.

About 6067 holiday rentals in Oahu boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Oahu for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Oahu with all the best amenities for your next trip.