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!

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Properties Available 84 properties available
Welcome to Sandy Seaclusion!Located in the quiet south end neighborhood of Toluca Landing and minutes to 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 heat
Sandy Seaclusion Pet Friendly
Home
$422.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 (143)
The Bungalows at St Simons Park Unit #640: Embrace coastal living in this beautifully renovated two-bedroom, two-bath retreat, just a short 57 minute walk from Pier Village and the islands sun-drenched beaches. Tucked away on a private, tranquil street, Unit #640 is one of four stylish bungalows sharing a sparkling community pool (Seasonal Pool Cl
New Listing! New Listing!
New Listing!
New Listing!
The Bungalows at St. Simons Park - # 640
Condo
$237.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (3)
Welcome to Salt Air Villas Unit 214!The private, gated Salt Air Villas community is a quiet condo community located a short 1/2 mile from the best beaches, restaurants and shopping on St. Simons Island! Unit 214 is a nicely updated king bed efficiency unit with a bunk room. Guests will have access to covered gated parking, the Salt Air Villas commu
Salt Air Villas #214
Condo
$150.00 / per night avg
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 (116)
Welcome to Georgia On My Mind, your private slice of St. Simons Island where the pace slows down, the air feels a little sweeter, and vacation begins the moment you arrive. Tucked away in the quiet neighborhood of St. Simons Heights, this inviting home offers the best of both worlds, a peaceful setting to truly unwind while keeping you close to eve
Georgia On My Mind
Home
$379.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (74)
Discover your perfect island retreat at 1152 East Peachtree St! Nestled ideally between seclusion and centrality, this beautifully renovated duplex offers a prime location just a short 0.2-mile stroll to beach access at Myrtle St. Whether you're seeking a peaceful hideaway or an exciting coastal adventure, this property is the ideal setting.115
Summertime Cottage
Home
$276.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.9 (39)
Welcome to Enchanted Getaway! Newly constructed in 2024, The Enchanted Getaway blends modern luxury with relaxed coastal charm and is located just one street from the beach and within an easy walk to the lively Pier Village area. Designed for memorable island vacations, this beautifully appointed home features an open-concept layout, a private pool
New Listing! New Listing!
New Listing!
New Listing!
Enchanted Getaway
Home
$672.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 4 baths / 1 half bath
Guests 12 guests
Rating 4.9 (13)
The Bungalows at St Simons Park Unit #638: Discover island-inspired style and comfort in this freshly updated two-bedroom, two-bath condo, just a 57 minute stroll from Pier Village and sun-kissed beaches. Nestled on a serene, private street, Unit #638 is one of four chic bungalows sharing a tranquil community pool (Seasonal Pool Closure starting O
New Listing! New Listing!
New Listing!
New Listing!
The Bungalows at St. Simons Park - # 638
Condo
$220.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Welcome to Under the Oaks! Located in a brand new community - 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, Under the Oaks is a special getaway right in the middle of everything.Guest reservations of 3
Under the Oaks
Home
$492.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 8 guests
Rating 4.9 (50)
Professionally furnished, the Atlantic Cottage has everything guests are looking for in the next St. Simons Island getaway! Offering 4 spacious bedrooms and 3.5 bathrooms, the Atlantic Cottage will allow guests to put their toes in the sand after a convenient 200-step walk to the beach access at the end of the street.From ocean front and marsh fron
Atlantic Cottage
Home
$567.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 9 guests
Rating 5 (83)
Planning a fun getaway to St. Simons Island, whether youre a solo traveler, couple, or group of family and friends promises to be an amazing experience. While youre likely looking forward to the peace, beauty, and tranquility to be found in this incredible location, that doesnt mean you cant pair those moments with resort-inspired amenities too! Th
St. Simons Grand 306
Condo
$462.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 guests
Rating 4.9 (148)
Welcome to Stay Salty! This recently redecorated, spacious East Beach cottage features two levels of wraparound porches allowing you to enjoy sweeping views of the marsh as well as plenty of outdoor living areas to relax and unwind.Guest reservations of 3 to 21 nights come with a valuable credit to use towards beach gear rentals during your stay! T
Stay Salty
Home
$1,097.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.9 (49)
Welcome to Beachology, a charming and spacious vacation retreat nestled in the inviting Demere Landing neighborhood of Saint Simons Island. This 2,300-square-foot coastal escape offers the perfect setting for families and friends looking to unwind and explore the beauty of the island. Whether you're seeking relaxation, adventure, or a little of
New Listing! New Listing!
New Listing!
New Listing!
Beachology Pet Friendly
Condo
$265.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 9 guests
Rating 4.9 (30)

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