Discover winter rentals Saint Simons Island - We found 874 exact matches
About Saint Simons Island Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Saint Simons Island, GA perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.
Vacation Cottage presents luxury options for travelers seeking to rent a place in Saint Simons Island. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Saint Simons Island and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Saint Simons Island Winter Rentals
What are the top rated Winter Rentals in Saint Simons Island?
There are a lot of options in Saint Simons Island. If you plan on staying in the Saint Simons Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Saint Simons Island:
- Sassy Peach Cottage - 5 Bed/4.5 Bath. Large Pool. Near Lighthouse/Pier/Village!
- Newly Renovated Oceanfront Condo Right on the Beach Beachfront Great Views
- Fall Beach Specials! SUPER SAVINGS! Email for Quote!
- Mermaid Cottage Priv Heated Pool! 4th Night Free September and October!
- Breath taking water views with huge lani
- The Penthouse at High Tide - Best Views Right on the Beach - Great for Families!
- Newer Construction - Short Walk to Beach - Hot Tub/Large Pool - 16' x 32'
- Gorgeous Upscale Villa, Short Walk to Beach and Pier!
- Big Luxury Island Style 5 Bed 3 Bath One level Sleeps 9 Quiet Street GR8 Locati
- Great Location! Charming Beach Cottage. 1 block to Beach
How much does it cost to rent a place to stay near Saint Simons Island in the wintertime?
The average cost for winter rentals in Saint Simons Island is $431 per night. Vacation Cottage 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.
Are there any winter cottages/chalets in Saint Simons Island that allow pets?
Yes, here are the top cottage/chalet rentals in Saint Simons Island that allow you to bring your pet or dog:
- JUST STEPS FROM THE OCEAN.
- Beach Club #414
- The King and Prince Beach & Golf Resort
- Oceanfront View from EVERY Room! Best Beach Club Condo!
See all pet-friendly vacation rentals in Saint Simons Island on Vacation Cottage
Do you have any winter rentals in Saint Simons Island that are suitable for families?
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.
Are there winter accommodations in Saint Simons Island that have indoor swimming pools?
As of 2026, the data from Vacation Cottage shows that there are over 874 private swimming pools or indoor pools accommodations near Saint Simons Island along with other great amenities.
Do any winter holiday rentals in Saint Simons Island have hot tubs?
About 874 holiday rentals in Saint Simons Island boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Saint Simons Island?
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.
