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 Live Oak Cottage, a charming haven nestled in the heart of Saint Simons Island. Ideally located just a short ride from the beach and the vibrant Village, this thoughtfully designed retreat blends coastal charm with modern comforts, creating the perfect getaway for families and friends. Whether youre seeking relaxation or adventure, Live
New Listing! New Listing!
New Listing!
New Listing!
Live Oak Cottage Pet Friendly
Home
$425.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (35)
Welcome to the Hamilton Cottage! This magnificent four-bedroom, four-bath vacation rental home is a cornerstone cottage in the award-winning Coast Cottages beachfront neighborhood. Located at the entrance to brick-paved Coast Cottage Ln, Hamilton Cottage has designer furnishings and all the comforts that any vacation property should have. Relax in
Hamilton Cottage
Home
$612.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 4 baths / 1 half bath
Guests 10 guests
Rating 4.7 (45)
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
$597.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 4 baths / 1 half bath
Guests 10 guests
Rating 4.9 (74)
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
$345.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 8 guests
Rating 4.9 (128)
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 4.8 (57)
Welcome to Beachy Keen at the North Breakers (Unit 404)! Beautifully remodeled inside and out, this gated ocean-view condo at the oceanfront community of North Breakers is a breathtaking home away from home for guests to enjoy on St. Simons Island. Conveniently located near the elevator, this two-bedroom, two-bathroom residence features an open-con
Beachy Keen
Condo
$542.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.9 (120)
Welcome to Beach Walker's Bliss! Nicely renovated, this 2 bedroom / 2 bathroom ground floor condo is located in the Ocean Walk Condominium complex - Unit L-1. Just a short 10 minute walk to the popular Pier Village Area, enjoy some of St. Simons Island's most popular restaurants and shops and even a dog park, community tennis and pickle bal
Beach Walker's Bliss Pet Friendly
Condo
$133.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.7 (25)
Welcome to Peachtree Oak Cottage, a charming island retreat located in the quiet neighborhood of St. Simons Heights. This inviting home offers the perfect mix of comfort, privacy, and convenience, with easy access to beaches, restaurants, and shopping on St. Simons Island. One of the standout features of this property is the spacious backyard and o
Peachtree Oak Cottage
Home
$311.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.9 (114)
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
$1,047.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.9 (55)
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
$385.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 guests
Rating 4.9 (108)
Welcome to Wading Inn, a stunning custom-built retreat in East Beach, completed in 2017 and proudly featured on the 2018 Christ Church Tour of Homes. Just a short stroll from the beach on the quiet stretch of Bruce Drive, this five-bedroom, five-and-a-half-bathroom home blends sophisticated coastal style with modern comforts, creating the perfect b
Wading Inn
Home
$1,400.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 5 baths / 1 half bath
Guests 16 guests
Rating 4.9 (118)
Welcome to Golden Sands Getaway, a stunning coastal retreat in Demere Landing on beautiful Saint Simons Island, GA. Perfectly situated just minutes from the islands pristine beaches, charming village, and top attractions, this spacious 3-bedroom, 3.5-bathroom condo offers the ideal mix of relaxation and adventure for families and groups. With an ex
New Listing! New Listing!
New Listing!
Golden Sands Getaway
Condo
$331.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 7 guests
Rating 5 (14)

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