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 83 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 porches provide guests w
High Tide
Home
$585.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 4 baths / 1 half bath
Guests 10 guests
Rating 4.9 (78)
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
$371.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 guests
Rating 4.9 (110)
Welcome to the Oak Beach Cottage!Nestled on a quiet street just a 4-minute walk to the St. Simons Island beach, this custom-built home has it ALL! The large 30x18 swimming pool and spa (can be heated upon request for an additional fee) is a resort-like escape for guests to enjoy the large backyard space with tropical palm trees and a poolside hammo
Oak Beach Cottage Pet Friendly
Home
$897.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 10 guests
Rating 4.9 (137)
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
$475.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 8 guests
Rating 4.9 (56)
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
$397.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (90)
Welcome to Coastal Crush! Location, Location, Location... get ready to have everything from the amazing St. Simons Island beaches to dining experiences right at your doorstep. This beautifully furnished, fully renovated townhome is one block from beach access. Once guests walk in the door, they will immediately feel the relaxation of island time wi
Coastal Crush
Condo
$327.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 8 guests
Rating 4.9 (129)
Welcome to the Sanderling Cottage!This completely remodeled 3 bedroom, 2 bathroom cozy cottage (sleeps 6) is dog-friendly, and located just a short 10-minute walk from the Village and Pier Area on St. Simons Island. This newly renovated vacation rental features a well-equipped kitchen that opens to a spacious living/dining area which overlooks the
Sanderling Cottage Pet Friendly
Home
$210.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (168)
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 (68)
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 (151)
Welcome to Rivera Retreat, a beautifully remodeled single-level home designed for guests seeking relaxation, comfort, and the true St. Simons Island local experience. This serene coastal escape has been expertly renovated and professionally decorated, offering a stylish, laid-back vibe for families or friends to unwind and reconnect.Guest reservati
New Listing! New Listing!
New Listing!
New Listing!
Rivera Retreat
Home
$500.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (27)
Welcome to Cozy Coastal Cottage! Newly renovated, this cute dog-friendly 3 bedroom / 2 bathroom cottage is located on a quiet street that is popular due to its close walking distance to the beach, shopping, restaurants, and the dog park! The open-concept kitchen, sitting area, and dining space are the perfect place to relax as a group. Adjacent is
Cozy Coastal Cottage Pet Friendly
Home
$270.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 (61)
Welcome to Goin' Coastal! Perfectly situated on 3rd Street in the much desired St. Simons Island East Beach neighborhood and a 1/4 mile to the 3rd St. beach access, Goin' Coastal offers its guests a wonderfully remodeled 5 bedroom / 4.5 bathroom home with a brand new heated pool.Guest reservations of 3 to 21 nights come with a valuable cred
Goin' Coastal
Home
$897.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 4 baths / 1 half bath
Guests 12 guests
Rating 4.9 (53)

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