St. Simons 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 71 properties available
Welcome to the Island Time Cottage! This fabulous 3 bedroom / 2 bathroom south island home, complete with a new heated (heated upon request) pool and beautiful backyard, is perfect place for you to find yourself on "island time".  Located in a great south island location, this home is minutes to the beaches, restaurants and shopping
Island Time Cottage
Home
$535.00 / per night avg
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to 337 Beach Club! This recently updated 2BR/2BA condo is located at the St. Simons Beach Club resort and is one of our many oceanfront condos on St. Simons Island.Sorry, pets are not allowed.Linens (Bath towels & bed sheets) as well as pool/beach towels providedCheck In: 4:00pm    Check out: 10:00amVillage area (7 m
Beach Club 337
Condo
$250.00 / per night avg
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.7 (64)
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
Salt Air Villas #214
Condo
$170.00 / per night avg
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 (25)
Welcome to Red Cedar Villa! Red Cedar Villa is a tropical haven among the gorgeous neighboring homes in the heart of St. Simons Island.  This location is ideal for a perfect family getaway.  Enjoy your own private plunge pool along with access to the Coast Cottages Community pool! This home has four levels plus a rooftop terrace and with
New Listing! New Listing!
New Listing!
Red Cedar Villa
Home
$400.00 / per night avg
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (1)
Welcome to Sandy Seaclusion! Located in the quiet south end neighborhood of Toluca Landing and minutes to the beaches, shopping and restaurants on St. Simons Island, Sandy Seaclusion has it all!  This dog friendly seaside escape offers 3 bedrooms and 2 bathrooms with a private fenced in backyard, an outdoor shower and a private pool which
Sandy Seaclusion Pet Friendly
Home
$495.00 / per night avg
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 (34)
Welcome to the More Fun Cottage!  This immaculate 4 bedroom / 3 bathroom island beach cottage is located in a quiet neighborhood just a few minutes away from beaches, restaurants and shopping of St. Simons Island!  The wrap around front porch and the chic coastal décor will lure guests into island living at it's finest!&nb
New Listing! New Listing!
New Listing!
More Fun Cottage
Home
$405.00 / per night avg
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.7 (9)
Welcome to The Hideaway! Centrally located on the island, The Hideaway provides the perfect mix of beaches, restaurants and shopping to enjoy.  The homes spectacular backyard invites you to enjoy the spacious outdoor living space, private heated pool, and a game of corn-hole.  This home is the perfect St. Simons Island getaway with someth
New Listing! New Listing!
New Listing!
The Hideaway
Home
$442.50 / per night avg
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (5)
Welcome to Beach Haven! This beautifully appointed townhome, with a private elevator to all levels, is located just steps away from one of the best beaches on St. Simons Island!  Once inside, you can either take the elevator or a few steps to the main living area where you will find a beautifully decorated living room open to the dining room a
Beach Haven
Condo
$382.50 / per night avg
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 (24)
Welcome to 618 Harbour Oaks! This second floor 2 bedroom / 2 bathroom St. Simons Island condo rental was beautifully remodeled in 2020 and is new to the vacation rental market.  Featuring an open living floorplan within a private gated community, 618 Harbour Oaks has everything guests will need during their St. Simons Island getaway! 
Harbour Oaks 618
Condo
$270.00 / per night avg
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.7 (33)
Welcome to Coastal Crush!  Location, Location, Location... get ready to have everything from the amazing St. Simons Island beaches to food at your doorstep. This beautifully furnished/ newly renovated townhome is 1 block from beach access.  Once guests walk in the door, they will immediately feel the relaxation of "island time"
Coastal Crush
Condo
$387.50 / per night avg
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (31)
Welcome to the Happy Tabby Cottage!   Any group gatherings and events at this property are limited to the number of occupants (6 persons). Events such as weddings, rehearsal dinners, etc. are not permitted.  Dogs (only) are allowed with a pet fee of $150/dog.  Linens (Bath towels & bed sheets) provided  Beach towel
Happy Tabby Cottage Pet Friendly
Home
$260.00 / per night avg
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.7 (46)
Welcome to the Sanabell Cottage!  This beautifully decorated 3 bedroom, 2 bathroom cute coastal cottage is the perfect retreat for St. Simons Island visitors.  Centrally located on St. Simons Island, guests will enjoy quick access to beaches, shopping and restaurants.  Once guests walk through the front door, they will instantly feel
Sanabell Cottage
Home
$230.00 / per night avg
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (49)

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