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
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 (50)
Welcome to the Blue Crab Cottage! Located in a brand new neighborhood - Orchard Place, this private cottage has everything your group will want for your next vacation to St. Simons Island! Minutes to the best beaches, shopping and restaurants on St. Simons Island, Blue Crab Cottage is a special getaway right in the middle of everything.Guest reserv
Blue Crab Cottage
Home
$437.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.9 (80)
Welcome to High Tide! This hidden gem is THE perfect villa to relax and enjoy some of the best marsh views on St. Simons Island! Situated in a secluded and quiet three home neighborhood on the marsh, High Tide has everything guests will want to enjoy island time. The large pool area and backyard space along with multi-level porches provide guests w
High Tide
Home
$622.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 4 bedrooms
Bathrooms 4 baths / 1 half bath
Guests 10 guests
Rating 4.9 (78)
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 (51)
A Wave From It All brings together the best parts of an East Beach family vacation: a private heated pool, putting green, spacious screened porch, multiple gathering spaces, and a convenient location near the beach. With room for up to 12 guests, this welcoming St. Simons Island home gives families plenty of space to spend time together while still
A Wave From It All
Home
$677.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 4 baths / 1 half bath
Guests 12 guests
Rating 4.9 (141)
Welcome to Porch Light Cottage! Just a 2-minute walk from the beach, lighthouse, park and Pier Village, this luxury 5-bedroom, 4-bath retreat (including a private pool house) offers the ideal mix of comfort, privacy, and unbeatable location. Nestled in the heart of St. Simons Islands historic Pier Village neighborhood, Porch Light Cottage has been
Porch Light Cottage Pet Friendly
Home
$788.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.9 (27)
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,
OakLynn Retreat
Home
$6,000.00 / per night
Beach Gear Included VayKLife
Bedrooms 5 bedrooms
Bathrooms 5 baths / 1 half bath
Guests 12 guests
Rating 5 (38)
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
$537.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 (198)
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
Rivera Retreat
Home
$500.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (29)
Welcome to Villa 187 at The King Prince Resort!Discover coastal luxury at this ground floor 3 bed, 3 bath condo that is truly one-of-a-kind. Nestled within The King Prince Resort, this villa offers an unparalleled experience of oceanfront bliss. Imagine waking up to the sound of waves, stepping onto your private patio with direct ocean views, and
King & Prince 187
Condo
$432.50 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.9 (38)
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
$450.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 3 bedrooms
Bathrooms 2 baths / 1 half bath
Guests 8 guests
Rating 4.9 (194)
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
The Bungalows at St. Simons Park - # 636
Condo
$250.00 / per night avg
Beach Gear Included VayKLife
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (14)

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