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 81 properties available
Welcome to High Tide!  This hidden gem is THE perfect villa to relax and enjoy some of the best marsh views on St. Simons Island!  Situated in a secluded and quiet three home neighborhood on the marsh, High Tide has everything guests will want to enjoy island time.  The large pool area and backyard space along with multi-level porche
High Tide
Home
$597.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.8 (32)
St. Simons Island is a vacation destination that beckons visitors to come and make the most of their scenic surroundings while also indulging in time relaxing. That balance is exactly what you’ll find when you book a stay in Sunshine Magnolia. New to the vacation rental home market, this 5-bedroom, 3-bath island cottage can easily host up to
Sunshine Magnolia
Home
$589.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 12 guests
Rating 4.8 (71)
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 packa
La Reina
Home
$1,672.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 16 guests
Rating 4.9 (13)
Welcome to the Coastal Village Retreat, a stunning vacation home nestled in the heart of Saint Simons Island, Georgia. This charming property offers a perfect blend of comfort and coastal charm, making it an ideal getaway for families or groups seeking relaxation and adventure. Located in the vibrant Village Area, the Coastal Village Retreat is jus
New Listing! New Listing!
New Listing!
New Listing!
Coastal Village Retreat Pet Friendly
Home
$290.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 (3)
Welcome to Beach Lawn Cottage, an iconic oceanfront escape on beautiful Saint Simons Island, where coastal elegance meets modern comfort in a newly reimagined setting. Freshly renovated and expanded with an additional bedroom and bathrooms, this luxury retreat now features six spacious bedrooms and six full bathrooms, offering ample space for up to
Beach Lawn Cottage
Home
$1,600.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 12 guests
Rating 4.8 (38)
Welcome to Serenity Oasis - Villa 2! A stunning duplex vacation rental nestled in the highly sought-after South End of Saint Simons Island. This brand-new, professionally designed retreat offers the perfect blend of modern luxury and coastal charm, making it the ideal getaway for families, groups of friends, or anyone looking for a high-end vacatio
New Listing! New Listing!
New Listing!
Serenity Oasis - Villa 2
Home
$312.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
When booking Summer Wind, unwinding in style is easier than ever during your St. Simons Island adventure. A new Heated Private Pool and Spa were completed in May 2023, making them available all year round!  Any group gatherings and events at this property are limited to the number of occupants (8 persons). Spring Break groups and events such a
Summer Wind
Home
$462.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 (85)
Welcome to the Magnolia House, a breathtaking vacation retreat situated in the heart of the charming Village area on Saint Simons Island, GA. This beautifully crafted home combines luxury, comfort, and Southern charm, offering the perfect escape for families and groups seeking both relaxation and adventure in one of Georgia's most beloved coast
New Listing! New Listing!
New Listing!
New Listings!
Magnolia House
Home
$635.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Welcome to Circle Cottage!  Located in the quiet and convenient St. Simon Heights neighborhood, this designer-decorated cottage offers guests a private pool (14x24) and spa (8x8) tucked into a secluded backyard.  Guests of Circle Cottage will enjoy quick access to the beaches, shopping, and restaurants! Take a quick bike ride or walk to t
Circle Cottage
Home
$466.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (37)
Welcome to 618 Harbour Oaks! This second floor 2 bedroom / 2 bathroom St. Simons Island condo rental has been beautifully remodeled and features an open living floorplan within a private gated community. 618 Harbour Oaks has everything guests will need during their St. Simons Island getaway!   Any group gatherings and events at this
Harbour Oaks 618
Condo
$220.00 / per night avg
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.8 (67)
If you’re the type of traveler that sets your sights on St. Simons Island in the name of fun and relaxation, then Stones Throw Cottage has your name on it. This home away from home is a fan-favorite thanks to its incredible location. Only 80 yards away from the beach, this south island hot spot is a new two-story option on the rental market.&
Stones Throw Cottage Pet Friendly
Home
$347.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.7 (77)
Welcome to Serenity Oasis - Villa 1! A stunning duplex vacation rental nestled in the highly sought-after South End of Saint Simons Island. This brand-new, professionally designed retreat offers the perfect blend of modern luxury and coastal charm, making it the ideal getaway for families, groups of friends, or anyone looking for a high-end vacatio
New Listing! New Listing!
New Listing!
Serenity Oasis - Villa 1
Home
$312.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (3)

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