Saint Simons Island Winter Rentals & Holiday Homes

Discover winter rentals Saint Simons Island - We found 716 exact matches

About Saint Simons Island Winter Rental on Execstays.com

Planning on a winter vacation in Saint Simons Island? Discover 716 places to stay in Saint Simons Island, for those traveling with their family, friends, in groups, or for a wedding retreat.

At Execstays, we have a wide range of listings for accommodations in Saint Simons Island, GA that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. Execstays winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Saint Simons Island winter accommodation starts at US $451, and the most popular properties in Saint Simons Island are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, Execstays will make your winter trip memorable.

Execstays offers a great deal for travelers planning on renting a place in Saint Simons Island, to enjoy these benefits and to book your winter vacation homes, go to Execstays filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Saint Simons Island and unlock even more amazing deals.

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Frequently Asked Questions About Saint Simons Island Winter Rentals

The average cost for winter rentals in Saint Simons Island is $451 per night. Execstays has a wide list of great winter places to stay near Saint Simons Island 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 Saint Simons Island that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Saint Simons Island on Execstays.com

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Saint Simons Island to find what works for you.
As of 2025, the data from Execstays.com shows that there are over 716 private swimming pools or indoor pools accommodations near Saint Simons Island along with other great amenities.

About 716 holiday rentals in Saint Simons Island 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 Saint Simons Island for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Saint Simons Island with all the best amenities for your next trip.