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Diamond Beach Winter Rentals & Holiday Homes

Discover winter rentals Diamond Beach - We found 314 exact matches

About Diamond Beach Winter Rental on SunSkiResorts

Planning a winter vacation in Diamond Beach? Discover 314 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Diamond Beach 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 Diamond Beach start at US $278. The most popular properties in Diamond Beach 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 Diamond Beach, 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 Diamond Beach and unlock incredible deals.

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Frequently Asked Questions About Diamond Beach Winter Rentals

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

The average cost for winter rentals in Diamond Beach is $278 per night. SunSki has a wide list of great winter places to stay near Diamond Beach 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 Diamond Beach that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Diamond Beach on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Diamond Beach to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 314 private swimming pools or indoor pools accommodations near Diamond Beach along with other great amenities.

About 314 holiday rentals in Diamond Beach 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 Diamond Beach for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Diamond Beach with all the best amenities for your next trip.