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 77 properties available
Welcome to the Oasis Cottage!  This wonderful island escape is centrally located and just a short walk to the beaches and the best village area shops, restaurants and sites on St. Simons Island. Guests of the Oasis Cottage will have their own private heated pool and spa (heated upon request for $45/night) with plenty of pool side seating and l
Oasis Cottage Pet Friendly
Home
$537.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (17)
Welcome to Village Revival! This newly renovated 3 bedroom / 3 bathroom village cottage vacation rental located in the heart of the St. Simons Island Village area is the perfect St. Simons Island hideaway! Guests will find that the cottage is a 1 minute walk to all the best Pier Village area restaurants, shopping as well as the St. Simons Isla
Village Revival
Home
$480.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 guests
Rating 4.9 (45)
Welcome to the Harvey House! Nestled in the tranquil Sea Palms golf course neighborhood, surrounded by majestic live oaks draped with Spanish moss, this fully renovated island haven is your perfect escape into island time. Featuring a new heated pool available for an additional $45/day, it’s an ideal spot for relaxation and fun under the sun.
New Listing! New Listing!
New Listing!
New Listing!
The Harvey House Pet Friendly
Home
$646.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (14)
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 (1)
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
$562.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 12 guests
Rating 4.8 (70)
Welcome to Beach Club 337!  Immerse yourself in coastal serenity at this renovated 2BR/2BA oceanview condo. Beach Club 337, located within the premier Beach Club resort on St. Simons Island. Just a brisk 7-minute bike ride away, the village area beckons with its quaint charm.  Guest reservations of 3 to 21 nights come
Beach Club 337
Condo
$220.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.8 (103)
Welcome to 30 Waterfront Dr. #332, a sophisticated coastal retreat nestled in the South Island area of Saint Simons Island, Georgia. This pet-friendly rental offers breathtaking marsh views, creating a serene and private sanctuary for your stay.  Spanning 1,550 square feet, this elegant three-bedroom, three-bathroom condo comfortably accommoda
30 Waterfront Dr. #332 Pet Friendly
Condo
$202.50 / per night avg
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.9 (18)
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 pl
New Listing! New Listing!
New Listing!
New Listing!
Ocean Pearl
Condo
$517.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.8 (19)
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 (30)
Welcome to Latitude Adjustment!    Any group gatherings and events at this property are limited to the number of occupants (13 persons). Events such as weddings, rehearsal dinners, receptions, etc. are not permitted. Pets are NOT allowed Linens (bath towels, beach towels & bed sheets) provided Check In: 4:00pm 
Latitude Adjustment
Home
$695.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 13 guests
Rating 5 (42)
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
$322.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 5 (1)
Welcome to The Broadway Bungalow!  Located in the quiet and convenient St. Simon Heights neighborhood, this cottage offers guests a secluded backyard with plenty of space for the entire family.  Guests of The Broadway Bungalow  will enjoy quick access to the beaches, shopping and restaurants! Take a quick bike ride or walk to the fam
The Broadway Bungalow
Home
$280.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.7 (23)

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