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Gulf Harbor Winter Rentals & Holiday Homes

Discover winter rentals Gulf Harbor - We found 1706 exact matches

About Gulf Harbor Winter Rental on SunSkiResorts

Planning a winter vacation in Gulf Harbor? Discover 1706 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Gulf Harbor, 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 Gulf Harbor start at US $488. The most popular properties in Gulf Harbor 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 Gulf Harbor, 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 Gulf Harbor and unlock incredible deals.

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Frequently Asked Questions About Gulf Harbor Winter Rentals

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

The average cost for winter rentals in Gulf Harbor is $488 per night. SunSki has a wide list of great winter places to stay near Gulf Harbor 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 Gulf Harbor that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Gulf Harbor on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Gulf Harbor to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 1706 private swimming pools or indoor pools accommodations near Gulf Harbor along with other great amenities.

About 1706 holiday rentals in Gulf Harbor 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 Gulf Harbor for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Gulf Harbor with all the best amenities for your next trip.