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 Beach House!Nestled on a quiet street, just a 5-minute walk to the beach, this completely remodeled island cottage is the perfect south end escape for guests to enjoy ALL of the fun on St. Simons Island. The 8x14 heated (upon request in advance for $75/day) pool is a tropical escape for guests to enjoy privacy and the full island exp
The Beach House Pet Friendly
Home
$532.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 10 guests
Rating 4.9 (77)
The Bungalows at St Simons Park Unit #636: Step into your sunlit coastal sanctuary, just a short 57 minute walk from Pier Village and the islands pristine beaches. Thoughtfully renovated from top to bottom, this two-bedroom, two-bath condo blends breezy beach style with upscale finishes, nestled on a private, quiet street and sharing a sparkling c
The Bungalows at St. Simons Park - # 636
Condo
$250.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (14)
Nestled in the heart of East Beach, Enchanted Hideaway offers a luxurious oceanfront coastal retreat perfect for families and friends seeking relaxation and connection. This thoughtfully designed home boasts ocean views from the third level, a private heated pool, and multiple indoor and outdoor living spaces to create unforgettable memories on St.
Enchanted Hideaway
Home
$1,022.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 5 baths / 1 half bath
Guests 14 guests
Rating 4.9 (18)
Welcome to Golden Hour, a stunning vacation rental located in the picturesque East Beach area of Saint Simons Island. This spacious home offers a perfect blend of luxury and comfort, making it an ideal getaway for families or groups of friends looking to unwind and enjoy the coastal lifestyle.Guest reservations of 3 to 21 nights come with a valuabl
Golden Hour Pet Friendly
Home
$800.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 4 baths / 1 half bath
Guests 12 guests
Rating 4.9 (40)
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 (139)
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
$600.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 4 baths / 1 half bath
Guests 10 guests
Rating 4.7 (49)
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
$1,475.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 6 bedrooms
Bathrooms 6 baths / 1 half bath
Guests 12 guests
Rating 4.9 (74)
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 (65)
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 (114)
Welcome to the spectacular Seahorse Villa! Enjoy blue skies, gorgeous ocean views, and your very own private pool when you vacation at Seahorse Villa on St Simons Island! A short distance to the popular Coast Guard Beach for fun in the sun, this lovely 3,610 sq. ft.multi-story new home offers fantastic amenities for the perfect beach getaway.Guest
Seahorse Villa
Home
$772.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.9 (98)
Shore Rush Cottage offers a serene and sophisticated escape in the heart of the Sea Palms community on Saint Simons Island. Surrounded by the natural beauty of the coastal marshlands and nestled near the manicured fairways of the renowned Sea Palms Golf Club, this luxury single-level retreat combines upscale comfort with the timeless relaxation of
Shore Rush Cottage Pet Friendly
Home
$475.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.9 (18)
Welcome to Stones Throw Cottage, a two story retreat on the south end of St. Simons Island that blends relaxed coastal style with an easy, walkable location. Just an 80 yard walk from the beach and close to the Village, pier, parks, shops, and local restaurants, this home offers a comfortable setting for island days and unrushed evenings. With two
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 4.9 (197)

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