As the fall season continues here in the Lowcountry, vacation planners and property management groups alike are prepping for end of year trips. As the cool weather rolls across the United States, those in colder climates may be keen to escape to the docile weather of the South. The Charleston Coast is the perfect place to spend the holidays, between our Thanksgiving and Christmas availability and those monthly winter rentals, the options are endless!
From quiet beach towns to that beloved southern hospitality, the islands across Charleston are calling for this holiday season. Now all you need is the perfect property with a large kitchen for cooking, a vast dining table for serving up the family, and a welcoming space that feels like home away from home. Lucky for you, we’ve got options!
Kiawah Island Vacation Rentals
5556 Cypress Point
Located in the heart of Kiawah Island, 5556 Cypress Point is a new property on our program offering luxury design elements, cozy coastal decor and an open floor plan perfect for families looking to celebrate together. Featuring a dining table for six, a vast countertop in the kitchen with a built-in wine fridge and a remarkable gas stove nestled amongst the fully equipped kitchen, this is the perfect place for a holiday dinner. With 4 bedrooms, 4.5 bathrooms and sleeping up to 10 guests, this property is the ideal location for a calm coastal getaway among the nature of Kiawah Island.
1232 Greenslake
Another Kiawah Island treasure, 1232 Greenslake is a coastal retreat perfect for a family of six, with 3 bedrooms and 2.5 bathrooms. Right down the road from the Cougar Point Golf Course Clubhouse, this villa is a lagoon-view escape featuring an updated kitchen, bar seating, dining nook for six, along with a screened-in porch to enjoy that warm coastal weather while you’re enjoying the island. Even better, this home features community pool access, and is only a 10-minute walk to Kiawah beaches, biking and golf!
Seabrook Island Vacation Rentals
4013 Bridle Trail
Pivoting to Seabrook Island, we love the comfort this community has to offer for visitors far and wide. At 4013 Bridle Trail, this standalone home offers a 3 bedroom, 3 bathroom, 8 guest oasis that brings light and bright design elements to an open floor plan. The dining room table seats eight and is perfectly situated next to counter seating in the open kitchen. Just steps from the Seabrook Island Lake House, pools, playground, equestrian center and tennis courts, this Southern style home is superb for your next family getaway!
1727 Fiddlers Cove
Nothing screams Charleston Coast like marsh views from your private screened-in porch! This stunning Seabrook Island villa at 1727 Fiddlers Cove offers updated architectural design alongside a key coastal marsh. This 3 bedroom, 3 bathroom, 6 guest home is the perfect stay for those craving breathtaking views and a fully-equipped kitchen. With a dining room table for 6 guests, two island counter seats and a large sunken living room with floor to ceiling windows, this coastal getaway is a vacation experience that is hard to come by.
Isle of Palms Vacation Rentals
3 on 37th Avenue
Transitioning over to the Isle of Palms, this local beach town is the perfect spot to enjoy the holidays… especially as the area quiets down in the off-season! 3 on 37th Avenue is a centrally located gem just a short walk from the beach, Isle of Palms Marina and a quick golf cart ride to restaurants and shops. Featuring a private pool, rooftop deck, game room, and expansive open floor plan, this luxurious retreat is the perfect place for a large family to spend the holidays. With 6 bedrooms, 6.5 baths, and sleeping up to 14 guests, this massive home has a dining room table for six, counter seating for six more, and a remarkable gas stove alongside vast countertops – ready for your next spectacular Thanksgiving dinner.
2307 Hartnett Blvd.
Heading closer to the Isle of Palms connector, 2307 Hartnett Blvd. is another Isle of Palms jewel set for hosting a large family gathering coming into town for the holiday season. Featuring 5 bedrooms, 4.5 baths, and hosting up to 10 guests, this property has numerous amenities such as a private pool, golf cart, putting green, ping pong table, grill and is only a five minute walk to the beach. This home has an open plan on the main floor, with a large kitchen island that features four counter seats, a dining room table for eight, and a gas stove many would drool over!
4 on 53rd Avenue
Looking for a cozy beach house in a quiet and discrete corner of Isle of Palms? 4 on 53rd Avenue is the place to be this November. Hosting a family of up to 10, this 4 bedroom, 3.5 bath retreat is just 50 yards from the beach with partial ocean views throughout. Recently renovated, this sprawling floorplan boasts a sunken living room, a dining room table for eight, a secondary living room right off the kitchen and an open cooking setup with a serving window perfect for hosting. Just a short golf cart ride away are Wild Dunes amenities, the Isle of Palms Marina and golf courses galore!
Wild Dunes Vacation Rentals
416B Shipwatch
Last but most certainly not least is a stunning penthouse villa in the Wild Dunes gated community. 416B Shipwatch has stunning oceanfront views across the entire property, from its top floor porch to its open concept main floor. This Shipwatch Villa has 3 bedrooms, 3 baths, and hosts up to 8 guests. The main area of the property features a light and bright kitchen with a massive island that seats four. Even better, the main floor boasts a dining room table perfect for a holiday dinner, with seating for all eight guests. Located close to the Wild Dunes resort, dining, golfing, activities, and community events are abundant!
Your Holiday Sweetgrass Stay
Level up your holiday by staying with Sweetgrass Properties this Thanksgiving. Whether you’re looking for a spacious estate located beach-front with ocean views or a cozy coastal villa just steps from community clubhouses, we have a little bit of everything for every type of family.
Interested in booking your next trip to Charleston? Check out properties across islands like Kiawah, Seabrook, Isle of Palms and Wild Dunes for your next vacation and experience the Sweetgrass difference. Use code HOLIDAY150 to receive a $150 booking credit for your 2025 holiday stay!