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 The Bungalows at St. Simons Park, where your whole group can vacation together without giving up the comfort of having space to call their own. This one-of-a-kind St. Simons Island retreat brings together four beautifully renovated coastal bungalows to create an 8-bedroom, 8-bathroom getaway with a pool, perfect for extended families, co
Perfect for Groups! Perfect for Groups!
Perfect for Groups!
Perfect for Groups!
The Bungalows at St. Simons Park
Home
$1,400.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 8 bedrooms
Bathrooms 8 baths
Guests 18 guests
Welcome to Villa 148 at the King Prince Resort! Any group gatherings and events at this property are limited to the number of occupants (6 persons) Sorry, pets are not allowed Linens (bath towels, beach/pool towels bed sheets) provided Check In: 4:00pm Check out: 10:00am The King Prince does heat their main hotel pool during the cooler fall/spri
King & Prince 148
Condo
$425.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (259)
Welcome to Houdini by the Sea! This wonderful island escape is centrally located just a short walk to the beaches and the best village area shops, restaurants and sites on St. Simons Island. Guests of Houdini by the Sea will have their own private heated pool (heated upon request for $75/day) with plenty of pool side seating and lounging for use du
Houdini by the Sea
Home
$572.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 (63)
Welcome to the Highland House! This beautiful 3 bedroom / 2 bathroom home is located in a quiet neighborhood on the south end of St. Simons Island and is just 1 mile to the beach and the St. Simons Pier Village Area. From the moment you walk in the front door, you will feel as though you are at your home away from home. The primary suite features a
Highland House
Home
$171.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (152)
Welcome to the More Fun Cottage!This immaculate 4-bedroom / 3-bathroom island beach cottage is located in a quiet neighborhood just a few minutes away from beaches, restaurants, and shopping on St. Simons Island! The wraparound front porch and the chic coastal dcor will lure guests into island living at its finest! Recently updated and furnished, t
More Fun Cottage
Home
$400.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (66)
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 (82)
Welcome to Serenity Oasis Villa 2, a stunning duplex vacation home nestled in the highly sought-after South End of Saint Simons Island. This brand-new, professionally designed retreat blends modern luxury with coastal charm, creating the perfect haven for families, groups of friends, or anyone seeking a refined island escape. Serenity Oasis consist
Serenity Oasis - Villa 2
Home
$300.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 8 guests
Rating 5 (30)
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
Beachology Pet Friendly
Condo
$263.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 9 guests
Rating 4.9 (44)
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
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
The Bungalows at St Simons Park Unit #634: Welcome to your bright beach-inspired retreat just steps from the Pier Village and the golden sands of St Simons Island. This fully renovated two-bedroom, two-bath condo is one of four condos in a private and quiet street setting and shares a sparkling community pool(Seasonal Pool Closure starting October
The Bungalows at St. Simons Park - # 634
Condo
$250.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (7)
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
$450.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 guests
Rating 4.9 (159)
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 Island Pie
Village Revival
Home
$355.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 guests
Rating 4.9 (111)

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