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
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
Welcome to OakLynn Retreat, a stunning brand-new vacation home located in the heart of St. Simons Islands most sought-after neighborhoodEast Beach. Just a short walk to both the beach and marsh-side sunsets, this beautifully designed two-story retreat offers the perfect blend of upscale comfort, thoughtful design, and timeless island charm.Inside,
New Listing! New Listing!
New Listing!
New Listing!
OakLynn Retreat
Home
$753.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 5 baths / 1 half bath
Guests 12 guests
Rating 5 (28)
Discover your perfect island retreat at 1152 East Peachtree St! Nestled ideally between seclusion and centrality, this beautifully renovated duplex offers a prime location just a short 0.2-mile stroll to beach access at Myrtle St. Whether you're seeking a peaceful hideaway or an exciting coastal adventure, this property is the ideal setting.115
Summertime Cottage
Home
$325.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.9 (39)
Welcome to Salt Air Villas Unit 214!The private, gated Salt Air Villas community is a quiet condo community located a short 1/2 mile from the best beaches, restaurants and shopping on St. Simons Island! Unit 214 is a nicely updated king bed efficiency unit with a bunk room. Guests will have access to covered gated parking, the Salt Air Villas commu
Salt Air Villas #214
Condo
$150.00 / per night avg
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 (117)
Welcome to A Summer Hour Retreat. Visitors to St. Simons Island who want to stay in the center of the islands best experiences will find that this charming retreat places them within easy walking distance of the Village Pier, the ocean, local restaurants, boutique shops, and Neptune Park Fun Zone. While close to the action, the home also provides a
A Summer Hour Retreat Pet Friendly
Home
$464.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths / 1 half bath
Guests 6 guests
Rating 4.9 (222)
Welcome to Enchanted Getaway! Newly constructed in 2024, The Enchanted Getaway blends modern luxury with relaxed coastal charm and is located just one street from the beach and within an easy walk to the lively Pier Village area. Designed for memorable island vacations, this beautifully appointed home features an open-concept layout, a private pool
New Listing! New Listing!
New Listing!
New Listing!
Enchanted Getaway
Home
$647.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 4 baths / 1 half bath
Guests 12 guests
Rating 4.9 (14)
When booking Summer Wind, unwinding in style is easier than ever during your St. Simons Island adventure. A new Heated Private Pool and Spa were completed in May 2023, making them available all year round! Any group gatherings and events at this property are limited to the number of occupants (8 persons). Spring Break groups and events such as wedd
Summer Wind
Home
$445.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths / 1 half bath
Guests 8 guests
Rating 4.9 (179)
Emmeline Cottage invites guests to experience the rare blend of refined coastal luxury and timeless seaside charm that defines St. Simons Islands sought-after Coast Cottage community. Known for its picturesque streets, charming architecture, and private beachfront access, this exclusive neighborhood places you at the heart of island elegance, where
Emmeline Cottage
Home
$1,675.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 6 bedrooms
Bathrooms 6 baths / 1 half bath
Guests 14 guests
Rating 4.9 (48)
Professionally furnished, the Atlantic Cottage has everything guests are looking for in the next St. Simons Island getaway! Offering 4 spacious bedrooms and 3.5 bathrooms, the Atlantic Cottage will allow guests to put their toes in the sand after a convenient 200-step walk to the beach access at the end of the street. From ocean front and marsh fro
Atlantic Cottage
Home
$650.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 9 guests
Rating 5 (83)
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
$318.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 7 guests
Rating 5 (11)
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
$1,022.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.9 (52)
Welcome to Blue Skies Cottage! Travelers looking for a sensational getaway destination will find everything theyre looking for in the scenic landscape that makes up St. Simons Island. When you prefer to pair your experience with accommodations that make comfort, style, and charm a priority, look no further than looking into Blue Skies Cottage when
Blue Skies Cottage
Home
$225.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.9 (225)

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