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 (36)
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 4.8 (88)
Welcome to Lucy's Hideaway!This immaculate 4-bedroom / 2.5 bathroom island beach cottage is located in a quiet neighborhood just a few minutes away from beaches, restaurants, and shopping on St. Simons Island!Guest reservations of 3 to 21 nights come with a valuable credit to use towards beach gear rentals during your stay! The credit amount of
Lucy's Hideaway Pet Friendly
Home
$540.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (50)
Welcome to Villa 155 at the King Prince Resort! The beautifully renovated 2-bedroom / 2-bathroom ground-floor oceanfront condo is the perfect condo experience, giving guests everything that resort living has to offer on St. Simons Island. Located a short 1-minute walk to the main King Prince Resort Hotel building, guests will have access to full
King & Prince 155
Condo
$425.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (110)
Welcome to Latitude Adjustment!Welcome to Latitude Adjustment!Located in the south-end cul-de-sac neighborhood of Couper Place on St. Simons Island, this beautiful coastal escape has it all! Latitude Adjustment features 4 bedrooms, spacious living areas, and an outdoor pool living space that dreams are made of!Escape to your own private oasis! Gues
Latitude Adjustment
Home
$555.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 13 guests
Rating 5 (88)
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 (124)
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.
New Listing! New Listing!
New Listing!
New Listing!
Enchanted Hideaway
Home
$1,047.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 5 baths / 1 half bath
Guests 14 guests
Rating 4.9 (15)
Welcome to A Wave From It All! This spacious and perfectly suited East Beach cottage with a private pool is located exactly where you will want to be for your visit to St. Simons Island. Located between 2nd Street and 3rd Street, the cottage is a very short and easy walk to multiple beach access points (0.2 miles to the beach access at the Coast Gu
A Wave From It All
Home
$682.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 4 baths / 1 half bath
Guests 12 guests
Rating 4.9 (139)
Welcome to 432 Beach Club! This immaculate 2 bedroom / 2 bathroom condo has been and is the perfect getaway at The Beach Club on St. Simons Island. Just steps from the beach, this condo features stone and hardwood flooring throughout the spacious condo. Guest reservations of 3 to 21 nights come with a valuable credit to use towards beach gear renta
Beach Club 432
Condo
$235.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (175)
Welcome to the LighthouseCottage! Located 500 yards from the beautiful beaches on St. Simons Island, the Lighthouse Cottage is the perfect island escape for visitors to enjoy everything that the island has to offer, all within walking distance.Guest reservations of 3 to 21 nights come with a valuable credit to use towards beach gear rentals during
Lighthouse Cottage
Home
$362.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 (44)
Introducing Ocean Pearl, a stunning oceanfront condo perched on the top floor, perfectly positioned on St. Simons Island. Just steps from the iconic Pier and Village, Ocean Pearl offers a luxurious 2-bedroom, 2-bathroom retreat where the beauty of the ocean meets unparalleled convenience.Enjoy the spectacle of passing boats and playful dolphins rig
Ocean Pearl
Condo
$576.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 (194)
Dixie Sunrise welcomes guests to an elegant and thoughtfully designed coastal retreat in St. Simons Islands prestigious East Beach neighborhood. Known for its beach access, peaceful dune landscapes, and beautifully maintained residential streets, East Beach is one of the islands most desirable destinations. Staying at Dixie Sunrise places you just
Dixie Sunrise
Home
$1,050.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.9 (195)

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