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 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
$1,060.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.9 (52)
If your dream St. Simons Island escape includes the soothing rhythm of ocean waves, historic charm, and refined coastal living, then look no further than Vitamin Sea Cottage, your ultimate home away from home. Nestled in the heart of East Beach, one of the islands most treasured coastal enclaves, this beautifully restored 6-bedroom, 5-bathroom ocea
Vitamin Sea Cottage
Home
$997.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 4.9 (93)
Introducing Ocean Pearl, a stunning oceanfront condo perched on the top 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 rig
Ocean Pearl
Condo
$558.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 (187)
Shore Rush Cottage offers a serene and sophisticated escape in the heart of the Sea Palms community on Saint Simons Island. Surrounded by the natural beauty of the coastal marshlands and nestled near the manicured fairways of the renowned Sea Palms Golf Club, this luxury single-level retreat combines upscale comfort with the timeless relaxation of
New Listing! New Listing!
New Listing!
New Listing!
Shore Rush Cottage Pet Friendly
Home
$480.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.9 (12)
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 (225)
Welcome to The Broadway Bungalow, a warm and welcoming coastal retreat located in the quiet and convenient St. Simons Heights neighborhood. This charming cottage is designed for relaxation, connection, and easy island living, with a secluded backyard and inviting porch spaces that make it easy to slow down and enjoy your stay.Guests love the unbeat
The Broadway Bungalow
Home
$270.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (67)
Discover your perfect island retreat at 1150 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
The Livin's Easy Cottage
Home
$278.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (29)
Welcome to the spectacular Seahorse Villa! Enjoy blue skies, gorgeous ocean views, and your very own private pool when you vacation at Seahorse Villa on St Simons Island! Walk 125 yards and youll find yourself at the popular Coast Guard Beach for fun in the sun. This lovely 3,610 sq. ft.multi-story new home offers fantastic amenities for the perfec
Seahorse Villa
Home
$812.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.9 (94)
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
$267.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 9 guests
Rating 4.9 (31)
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 (151)
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
$437.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.9 (72)
Oleander Cottage is what beach vacation dreams are made of! This newly decorated home exudes coastal style at it`s finest. It`s attractive sophisticated, yet oh so comfortable! The plush furnishings will make your stay a relaxed experience! Any group gatherings and events at this property are limited to the number of occupants (10persons). Events
Oleander Cottage
Home
$442.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 (66)

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