1. USA
  2. Florida
  3. Tampa
  4. Grand Oaks
  5. Winter Rental

Grand Oaks Winter Rentals & Holiday Homes

Discover winter rentals Grand Oaks - We found 28 exact matches

About Grand Oaks Winter Rental on SunSkiResorts

Planning a winter vacation in Grand Oaks? Discover 28 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Grand Oaks, FL perfect for your seasonal escape. Our listings include private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments. SunSki's winter vacation homes feature top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winter accommodations in Grand Oaks start at US $189. The most popular properties in Grand Oaks include cabins, bungalows, and rental homes. Planning a snowboarding adventure? Explore our snowboard-friendly ski resorts, chalets, and cabins available for short-term or long-term stays. Whether it's a weekend getaway, monthly retreat, or an extended stay, SunSki ensures a memorable winter trip.

To book your winter vacation homes in Grand Oaks, visit SunSki's filter option, enter your travel dates, narrow down your preferences, and choose from our extensive list of rentals hassle-free. Explore our interactive map to uncover all accommodations in or around Grand Oaks and unlock incredible deals.

Show more
Show less

Frequently Asked Questions About Grand Oaks Winter Rentals

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

The average cost for winter rentals in Grand Oaks is $189 per night. SunSki has a wide list of great winter places to stay near Grand Oaks 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 Grand Oaks that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Grand Oaks on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Grand Oaks to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 28 private swimming pools or indoor pools accommodations near Grand Oaks along with other great amenities.

About 28 holiday rentals in Grand Oaks 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 Grand Oaks for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Grand Oaks with all the best amenities for your next trip.