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 82 properties available
Welcome to Beach Club 418!  One of eight 3 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 Sm
Beach Club 418
Condo
$325.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.7 (61)
When a tropical beach getaway is on your mind and you’re looking for accommodations that bring the luxury, comfort, and privacy to match, booking a stay at Casa De Playa is the perfect solution! This 4-bedroom, 3-bath St. Simons Island vacation rental with a heated pool (12x24) can comfortably accommodate up to 8 guests as well as two dogs fo
Casa De Playa Pet Friendly
Home
$596.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (148)
Welcome to the Island Pearl!  This beautifully updated vacation rental offers guests the perfect St. Simons Island escape with a private pool and tons of outdoor space for guests to relax and play.  Fully renovated in 2021, the Island Pearl is a short 5-minute drive to the beach (1.5 miles), the island's best restaurants and shopping.
Island Pearl
Home
$583.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 (34)
Welcome to La Reina! This magnificent six-bedroom East Beach oceanfront home enjoys incredible views, loads of privacy provided by a split floor plan, gorgeous hardwood floors, and a large separate guest house. Many details include an infinity edge heated saltwater pool and spa with a beautiful bluestone pool deck, a phenomenal appliance packa
La Reina
Home
$1,672.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 16 guests
Rating 4.9 (13)
Welcome to the Coastal Village Retreat, a stunning vacation home nestled in the heart of Saint Simons Island, Georgia. This charming property offers a perfect blend of comfort and coastal charm, making it an ideal getaway for families or groups seeking relaxation and adventure. Located in the vibrant Village Area, the Coastal Village Retreat is jus
New Listing! New Listing!
New Listing!
New Listing!
Coastal Village Retreat Pet Friendly
Home
$290.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 (3)
Welcome to the Lighthouse Cottage!  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 gea
Lighthouse Cottage
Home
$362.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (20)
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 po
Oak Beach Cottage Pet Friendly
Home
$842.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 (61)
Welcome to Moon Dance Cottage, a classic St. Simons Island retreat tucked away on one of the island’s most peaceful and sought-after streets. Located just steps from the beach and within easy walking or biking distance to the Village, pier, shops, and restaurants, this inviting 3-bedroom, 3-bath home offers the perfect blend of comfort, charm
New Listing! New Listing!
New Listing!
New Listing!
Moon Dance Cottage
Home
$300.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
When you’re excited about a month-long getaway and can’t 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 they’re looki
Sea Palms Colony
Condo
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Welcome to the Georgia On My Mind!  Located in the quiet neighborhood of St. Simons Heights, this home has the perfect amenity mix of location to beaches, restaurants and shopping, pool as well as lots of living spaces to enjoy on St. Simons Island.  Guests will immediately be drawn to the large screen porch that spans the entire width of
Georgia On My Mind
Home
$405.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (35)
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
$1,600.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 12 guests
Rating 4.8 (38)
Welcome to Latitude Adjustment!    Any group gatherings and events at this property are limited to the number of occupants (13 persons). Events such as weddings, rehearsal dinners, receptions, etc. are not permitted. Pets are NOT allowed Linens (bath towels, beach towels & bed sheets) provided Check In: 4:00pm 
Latitude Adjustment
Home
$695.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 13 guests
Rating 5 (42)

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