St. Simons Island Winter Rentals

Cozy and Charming Accommodations for Your St Simons Island Vacation

Whether you’re looking for a multi-level winter rental that can accommodate a large group or don’t need anything more than a cozy bungalow near the beach made for two, the team at Lilmar Vacations has a portfolio of houses to rent St Simons Island GA made to match. Guests who book into any of our winter rentals will enjoy spacious and bright floor plans that maximize not only square footage, but the allowance of natural light throughout the home. Many of our winter rentals come with fully equipped or gourmet-style kitchens complete with utensils and cookware as well as beautiful countertops, high-end appliances and ample cabinet space for storage. Beautifully furnished homes take both color palette and comfort into consideration and often enjoy a collection of upscale sofas and armchairs that are as eye-catching as they are inviting. Guests can make the most of a wonderful night’s rest on a comfortable mattress before waking up and enjoying a cup of coffee on a private balcony or patio.
Keeping connected can be a priority for many of our guests, even those who are looking to unwind and escape the hustle and bustle of everyday life. Guests who book our winter rentals on St. Simons Island will enjoy choosing from a collection of properties that are often equipped with access to Wi-Fi or high-speed internet for peace of mind and convenience during your stay. Take time to send those fun vacation photos to loved ones back home or keep up on current events at the touch of a button. As many of our homes are also furnished with large flat-screen televisions, wi-fi or high-speed internet connections makes it simple for guests to stream shows and movies on those evenings when they aren’t out exploring the island.

Luxurious Details

No matter how you’re planning on spending your winter St Simons Island vacation, our team is here to make sure your accommodations come with the fine details you deserve. Be sure to ask us about our winter rentals that include private hot tubs, extended balconies, multiple fireplaces or outdoor firepits. We’re happy to help our guests find a winter rental that comes with pet-friendly extras as well as properties that include ocean views or private gardens made for relaxing and indulging in winter beauty. From extra storage space to recommendations on the best winter stops on St. Simons Island, we’re dedicated to helping you experience a stay that’s truly one of a kind.

There’s Something for Everyone to Enjoy on St. Simons Island

Taking time to unwind in the winter on St. Simons Island is a treat, especially when you’re booked into a cozy rental with Lilmar Vacations that hosts all of the amenities, luxuries, and comforts you could ever imagine. While it’s tempting to cozy up indoors and enjoy your time away, winter is still a season for exploration and fun on St. Simons Island beyond the front door of your rental home. When you’re here this time of year, be sure to add a few of these stops to your itinerary to make your trip truly unforgettable.

Take to the Sky

When you’re looking for a vacation that comes with a thrill and a brand- new perspective, booking a tour with St. Simons Island Helicopter Tours is an absolute must. Gear up and head out alongside an experienced and knowledgeable pilot who will not only show you amazing sights from a bird’s eye view but offer up insight into the history of the island as well!

Enjoy the View from the Ground

No matter what season you visit St. Simons Island, a stop at the St. Simons Island Lighthouse and Museum is essential. This icon of the island is easy to spot with its pristine white exterior stretching up into the sky. The lighthouse sits on the southern end of the island and is a great place to grab a photo and earn some insight into the history of the island that’s deeply rooted in maritime culture. A trip through the museum is a wonderful way to imagine what it would require to be a lighthouse keeper while a trip up to the observation deck of the lighthouse is sure to be an inspiring moment you won’t soon forget.

Book Our Rentals

St. Simons Island is calling and there’s no better time than winter to step away from the grind of everyday life and enjoy a beautiful vacation. Contact our team today when you’re ready to start planning your trip!

.


Properties Available 85 properties available
Welcome to Blue Heaven, a beautifully renovated four-bedroom, three-and-a-half-bath vacation home located just steps from the soft, wide sands of East Beach, one of St. Simons Islands most sought-after destinations. This spacious retreat offers over 2,500 square feet of coastal-inspired living space designed for relaxation and connection. Guests ca
Blue Heaven
Home
$647.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 10 guests
Rating 4.9 (84)
Introducing Ocean Pearl, a stunning oceanfront condo perched on the third floor, perfectly positioned on St. Simons Island. Just steps from the iconic Pier and Village, Ocean Pearl offers a luxurious 2-bedroom, 2-bathroom retreat where the beauty of the ocean meets unparalleled convenience.Enjoy the spectacle of passing boats and playful dolphins r
Ocean Pearl
Condo
$519.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 (202)
Welcome to Sand Dollar Cottage! Tucked beneath the canopy of St. Simons Islands iconic live oaks and just steps from the beach, this inviting home blends Southern charm with coastal beauty and modern comfort. Located in the sought-after South End neighborhood, it offers the best of island living, quiet, breezy porches, and easy access to some of St
New Listing! New Listing!
New Listing!
New Listing!
Sand Dollar Cottage Pet Friendly
Home
$588.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 10 guests
Rating 5 (6)
Welcome to Coastal Crush! Location, Location, Location... get ready to have everything from the amazing St. Simons Island beaches to dining experiences right at your doorstep. This beautifully furnished, fully renovated townhome is one block from beach access. Once guests walk in the door, they will immediately feel the relaxation of island time wi
Coastal Crush
Condo
$330.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 8 guests
Rating 4.9 (131)
Welcome to the Blue Crab Cottage! Located in a brand new neighborhood - Orchard Place, this private cottage has everything your group will want for your next vacation to St. Simons Island! Minutes to the best beaches, shopping and restaurants on St. Simons Island, Blue Crab Cottage is a special getaway right in the middle of everything.Guest reserv
Blue Crab Cottage
Home
$411.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.9 (80)
Welcome to The Retreat on Gould, a beautifully updated coastal sanctuary nestled in the heart of the scenic Village area of St. Simons Island. This thoughtfully reimagined home blends timeless Southern charm with sophisticated modern updates, creating the ideal setting for relaxation, connection, and unforgettable island memories.Designed with both
The Retreat on Gould
Home
$525.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.9 (35)
When youre excited about a month-long getaway and cant wait to find accommodations that capture the essence of St. Simons Island living, a stay in Sea Palms Colony is bound to please. Guests who love the idea of indulging in a private retreat that still keeps them within proximity to island fun will find everything theyre looking for and more!Sea P
Sea Palms Colony
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Welcome to Blue Skies Cottage! Travelers looking for a sensational getaway destination will find everything theyre looking for in the scenic landscape that makes up St. Simons Island. When you prefer to pair your experience with accommodations that make comfort, style, and charm a priority, look no further than looking into Blue Skies Cottage when
Blue Skies Cottage
Home
$225.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.9 (235)
Welcome to the LighthouseCottage! Located 500 yards from the beautiful beaches on St. Simons Island, the Lighthouse Cottage is the perfect island escape for visitors to enjoy everything that the island has to offer, all within walking distance.Guest reservations of 3 to 21 nights come with a valuable credit to use towards beach gear rentals during
Lighthouse Cottage
Home
$357.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 (52)
Welcome to La Reina!This magnificent six-bedroom East Beach oceanfront home enjoys incredible views, loads of privacy provided by a split floor plan, gorgeous hardwood floors, and a large separate guest house. Many details include an infinity edge heated saltwater pool and spa with a beautiful bluestone pool deck, a phenomenal appliance package on
La Reina
Home
$1,745.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 6 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 16 guests
Rating 4.9 (39)
Welcome to Wading Inn, a stunning custom-built retreat in East Beach, completed in 2017 and proudly featured on the 2018 Christ Church Tour of Homes. Just a short stroll from the beach on the quiet stretch of Bruce Drive, this five-bedroom, five-and-a-half-bathroom home blends sophisticated coastal style with modern comforts, creating the perfect b
Wading Inn
Home
$1,272.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 5 baths / 1 half bath
Guests 16 guests
Rating 4.9 (120)
Welcome to Sandy Seaclusion!Located in the quiet south end neighborhood of Toluca Landing and minutes from the beaches, shopping, and restaurants on St. Simons Island, Sandy Seaclusion has it all! This dog-friendly seaside escape offers 3 bedrooms and 2 bathrooms with a private fenced-in backyard, an outdoor shower, and a private pool, which can be
Sandy Seaclusion Pet Friendly
Home
$405.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 (156)

Tell us what you're looking for and someone will contact you with available options.

I agree