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 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
$967.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 10 guests
Rating 4.9 (131)
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
$447.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (109)
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
$327.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 7 guests
Rating 5 (13)
The Bungalows at St Simons Park Unit #634: Welcome to your bright beach-inspired retreat just steps from the Pier Village and the golden sands of St Simons Island. This fully renovated two-bedroom, two-bath condo is one of four condos in a private and quiet street setting and shares a sparkling community pool(Seasonal Pool Closure starting October
New Listing! New Listing!
New Listing!
New Listing!
The Bungalows at St. Simons Park - # 634
Condo
$236.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (5)
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 (85)
Welcome to Villa 148 at the King Prince Resort! Any group gatherings and events at this property are limited to the number of occupants (6 persons) Sorry, pets are not allowed Linens (bath towels, beach/pool towels bed sheets) provided Check In: 4:00pm Check out: 10:00am The King Prince does heat their main hotel pool during the cooler fall/spri
King & Prince 148
Condo
$447.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (254)
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 (230)
Welcome to Blue Heaven, a beautifully renovated four-bedroom, three-and-a-half-bath vacation home located just steps from the soft, wide sands of East Beach, one of St. Simons Islands most sought-after destinations. This spacious retreat offers over 2,500 square feet of coastal-inspired living space designed for relaxation and connection. Guests ca
Blue Heaven
Home
$697.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 10 guests
Rating 4.9 (77)
Welcome to RedFish Retreat, a spacious and inviting vacation condo atDemere Landing on St. Simons Island, GA. With 2,300 square feet of thoughtfully designed space, this four-bedroom, three-and-a-half-bathroom retreat comfortably accommodates up to 10 guests and is dog-friendly, making it ideal for families and friends looking for a relaxing island
New Listing! New Listing!
New Listing!
New Listing!
RedFish Retreat Pet Friendly
Condo
$275.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths / 1 half bath
Guests 10 guests
Rating 4.9 (18)
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
$430.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths / 1 half bath
Guests 8 guests
Rating 4.9 (188)
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 (23)
Welcome to Beach Club 418! One of eight3 bedroom / 3 bathroom condos at the Beach Club, unit 418 is ready to welcome you to your next St. Simons Island vacation! Newly updated decor with wonderful top-floor ocean views, unit 418 will become guests' go-to condo within the Beach Club. The living room features a large HD Smart TV with cable televi
Beach Club 418
Condo
$325.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.8 (128)

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