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!

.


Properties Available 83 properties available
Welcome to Moon Dance Cottage, tucked away on one of St. Simons Islands most peaceful and sought-after streets. This timeless coastal retreat now features a brand-new heated pool, creating the perfect balance of relaxation and island luxury (pool heating: additional $75/night upon request). Designed to capture the essence of St. Simons living, Moon
New Listing! New Listing!
New Listing!
New Listing!
Moon Dance Cottage
Home
$382.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (8)
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 (46)
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
$479.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths / 1 half bath
Guests 6 guests
Rating 4.9 (228)
Welcome to 30 Waterfront Dr. #332, a sophisticated coastal retreat nestled in the South Island area of Saint Simons Island, Georgia. This pet-friendly rental offers breathtaking marsh views, creating a serene and private sanctuary for your stay.Spanning 1,550 square feet, this elegant three-bedroom, three-bathroom condo comfortably accommodates up
30 Waterfront Dr. #332 Pet Friendly
Condo
$225.00 / per night avg
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.9 (61)
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
$576.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 (191)
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 The Broadway Bungalow, a warm and welcoming coastal retreat located in the quiet and convenient St. Simons Heights neighborhood. This charming cottage is designed for relaxation, connection, and easy island living, with a secluded backyard and inviting porch spaces that make it easy to slow down and enjoy your stay.Guests love the unbeat
The Broadway Bungalow
Home
$270.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (68)
The Bungalows at St Simons Park Unit #640: Embrace coastal living in this beautifully renovated two-bedroom, two-bath retreat, just a short 57 minute walk from Pier Village and the islands sun-drenched beaches. Tucked away on a private, tranquil street, Unit #640 is one of four stylish bungalows sharing a sparkling community pool (Seasonal Pool Cl
New Listing! New Listing!
New Listing!
New Listing!
The Bungalows at St. Simons Park - # 640
Condo
$236.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.8 (5)
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
New Listing! New Listing!
New Listing!
New Listing!
The Bungalows at St. Simons Park - # 636
Condo
$236.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (10)
Welcome to the Water Lily Cottage!Located in the much-desired oceanfront community of Coast Cottages, this charming 3 bedroom / 3 bathroom home has it all! Views of marshes from three coastal front porch balconies will rock all of your worries away while you view the wildlife at your doorstep. Located only 325 yards from the ocean front Coast Cotta
Water Lily Cottage
Home
$482.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (136)
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
$372.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 guests
Rating 4.9 (107)
Welcome to Peachtree Oak Cottage, a charming island retreat located in the quiet neighborhood of St. Simons Heights. This inviting home offers the perfect mix of comfort, privacy, and convenience, with easy access to beaches, restaurants, and shopping on St. Simons Island. One of the standout features of this property is the spacious backyard and o
Peachtree Oak Cottage
Home
$303.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.9 (114)

Tell us what you're looking for and someone will contact you with available options.

I agree