So you’ve narrowed down exactly where you want to travel for your next big trip, and you’re heading to Charleston, South Carolina! Now, the planning truly begins. Whether you’re booking a stay for you and your significant other, your family or your next vacation with the crew, we have the perfect itinerary for any kind of getaway. All you have to do is book with Sweetgrass Properties, we’ll handle it from there!
Charleston Getaway for Couples
Where to Stay
1903 Bohicket Marina Villa - Seabrook
Tucked just steps from the Bohicket Marina, 1903 Bohicket Marina Villa is a 1 bedroom, 2 bathroom villa that sleeps 2 Guests. This condo is the perfect ground floor retreat with water views of the river and easy access to restaurants on the waterfront such as Fischer’s Pub and Salty Dog. With a light and airy coastal design and plenty of room for cooking on site, this villa is ideal for a couple’s escape. H4: 6B Seagrove Villa - Wild Dunes
Looking for a resort style getaway near Isle of Palms? We’ve got you covered. 6B Seagrove Villa is 2 bedroom, 2 bath, second floor unit with a private porch, expansive living and dining space, and is just steps away from the Atlantic shoreline. Even better, this condo is just a short walk to Wild Dunes amenities and the Seagrove community pool.
1903 Bohicket Marina Villa
What To Do
Book a Sunset Sail with Charleston Harbor Sailing
Nothing says romance like a Charleston sail as the sun sets below the horizon. Charleston Harbor Sailing offers $25 off your sunset sail when booking with Sweetgrass and allows you to bring your own food and drinks on the evening sail. Even better, you can pair your sail with photography for the perfect romantic experience!
Rent Bikes with Holy City Bikes
We love experiencing the Lowcountry by bike, and getting to book high quality gear with Holy City Bikes makes it even better. Servicing Isle of Palms and Wild Dunes only, Holy City Bikes delivers to your door with top notch bikes and helmets, so you can explore the area with your partner safely. Enjoy 20% off your booking when you stay with Sweetgrass!
Charleston Harbor Sailing
Where to Eat
Hege’s
A local French bistro tucked amongst the ivy within Freshfields Village, this coastal escape is the perfect couples dinner for those staying on Kiawah or Seabrook Island. One of the only finer dining spots near the island, Hege’s is a cozy restaurant featuring French specialties like Escargot and one of the best French Onion soups you’ll find in Charleston.
Code Del Pesce
Known as a local’s favorite, so don’t tell the Charlestonians that we’re sharing our favorite Italian in the area with visitors! Authentic Italian tucked quietly into Front Beach on Isle of Palms, Coda Del Pesce is an ocean-front hotspot that has some of the best Italian in the area. Featuring fresh local seafood and a seasonally changing menu, we can’t recommend this place enough!
Charleston Getaway for a Families
Where to Stay
296 Marsh Cove - Kiawah
Located amongst the expansive oaks and vast fairways of Kiawah Island is a standout Kiawah gem just waiting to host your whole family — and then some. 296 Marsh Cove is a 4 bedroom, 4.5 bath property that sleeps 10 guests and features a private saltwater pool, a downstairs game room, and plenty of primary living space for the family to spread out. Enjoy your own private Kiawah oasis!
3700 Palm Blvd. - Isle of Palms
Family vacation requires an ocean-front paradise, and we deliver! 3700 Palm Blvd. is a 5 bedroom, 4.5 bath home that sleeps 12 guests and features multiple floors of fun for the whole family. Ocean-front with its own private boardwalk to the beach, this property also boasts a vast backyard perfect for yard games, with two back porches perfect for soaking up those Isle of Palms ocean views.
296 Marsh Cove
What To Do
Head to The Goatery for a Day on the Farm
If you’re staying out on Kiawah or Seabrook, nothing can beat a day at the farm within the Kiawah River neighborhood at The Goatery. This local farm boasts goats — of course — chickens, pigs, donkeys, and steer. Family-owned and maintained, this standout little farm is the perfect adventure for kids to meet the animals, experience sustainable farming, and even pick up some goodies like farm fresh eggs. Get 15% off plus a small gift when you book with Sweetgrass!
Rent a Boat for the Family with Quarterdeck Boat Rentals
It’s not a Charleston vacation without a day spent on the waterways! Quarterdeck boat rentals and charters serve nearly the entire Charleston coastline, and your family can rent your boat from the IOP Marina for a day excursion or from the Bohicket Marina if you’re staying on Kiawah or Seabrook. When you mention Sweetgrass at checkout, you can receive 10% off your booking.
The Goatery
Where to Eat
Salty Dog - Seabrook Island
Featuring wide open outdoor spaces for the kids to run around, live music on weekends, and plenty of outdoor and indoor space no matter your group's size, Salty Dog is always a hit across generations. With a fun gift shop, delicious dining options like their classic Hush Puppies and Fisherman’s Pasta, this memorable spot is the perfect place for families staying on Kiawah or Seabrook.
Heavy’s Barburger - Isle of Palms
Newly open on Isle of Palms, we’re a sucker for Heavy’s Barburger. You’ve never had a smashburger quite like this. These heavenly patties are now being grilled up just steps from the Isle of Palms shoreline on Front Beach, and this spot is a vibrant, casual dining restaurant perfect for families on the go looking to enjoy a great — and hearty — meal.
Charleston Getaway for a Girls Weekend
Where to Stay
3729 Seabrook Island Road - Seabrook
The perfect girls weekend isn’t complete without a cute little beach bungalow to come home to. Our personal favorite getaway is 3729 Seabrook Island Road, a 3 bedroom, 2 bath home that sleeps 6 guests. With beachy design elements throughout, a sunbathing porch perfect for tanning, and just steps from the Seabrook shoreline, this ocean cabin is the place to be!
3101 Waterway Blvd. - Isle of Palms
3101 Waterway Blvd. will leave your crew gasping! Located just off the Intracoastal Waterway with both water and golf course views, this stunning property features 4 bedrooms, 3 baths and sleeps up to 10 guests. From its expansive swimming pool with spa, abundance of sun loungers and pool swings, screened-in porch and luxury design, this property is the perfect Isle of Palms stay for a large group, girl’s getaway!
3101 Waterway Blvd.
What To Do
Book Dinners by Derin for a Private Chef Dinner
It’s not a luxury vacation without booking a private chef for dinner one night, and we’ve got all the recommendations. For your girl’s trip, we highly recommend Dinner’s by Derin. A local, private chef specializing in home-made pasta, local seafood, lowcountry boils and Turkish cuisine, Derin is a rockstar at catering to your groups requests and special allergies. Even better, she even hosts a Pasta-Making Night for you and your crew to learn how to make hand-made, home-made noodles! Now serving Kiawah, Seabrook, Isle of Palms and Wild Dunes.
Rent Scooters to Explore the Area with Chucktown Scooters
It’s not an Isle of Palms vacation with the girls unless you’re booking Chucktown Scooters. Adorable, pastel-colored scooters delivered right to your door, these fun vespas are the perfect way to get around the island in style. Even better, they’re legal to ride from Isle of Palms over to local-favorite Sullivan’s Island, and can even cross the bridge into Mount Pleasant for days spent on Shem Creek. Enjoy 10% off your ride when you stay with Sweetgrass!
Chucktown Scooters
Where to Eat
Cafe Eugenia
Located in Freshfields Village between Kiawah and Seabrook Island’s, Cafe Eugenia is the perfect catch-all spot for coffee, treats, made-to-order lunch specials, to-go meals, take-out and more! One of our personal favorite spots, Cafe Eugenia prioritizes fresh and healthy, seasonal favorites that make it the perfect spot to stop in daily for breakfast or to sit down and enjoy during a Freshfields shopping day.
Little Palm
If you’ve been planning a girls getaway in Charleston, you’ve most likely seen Little Palm. Located inside The Ryder Hotel but open to the public, Little Palm is a pink dream perfect for your next girl’s trip. With a private pool where you can book a cabana and a day pass, an expansive outdoor patio with fire pits for those colder winter months, an indoor and outdoor bar along with delicious food and Instagrammable drinks? What more could you ask for!
Charleston Getaway for a Boys Weekend
Where to Stay
541 Front Nine Lane - Kiawah
No property has ever paired more perfectly with an Ocean Course tee time. 541 Front Nine Lane is a 5 bedroom, 5 bath modern marvel that sleeps 12 guests just a short drive from Kiawah’s legendary Ocean Course. With golf course and ocean views from the rooftop deck, this home features standout elements that define it from its Ocean Park neighbors. Enjoy modern design features paired with luxury amenities such as the expansive first floor patio, private pool and spa, screened porch, and elevator!
4 on 22nd Avenue - Isle of Palms
4 on 22nd Avenue is a beach bungalow perfect for any kind of group. With five bedrooms, 3.5 baths and sleeping 12 guests, this expansive home feels quaint while still being ideal for spreading out throughout the home. Just 100 yards from the beach, with its own private pool, game room, and outdoor putt-putt green, this is the ideal spot for a guy’s getaway.
541 Front Nine Lane
What To Do
Schedule a Fishing Charter with 4 Sons Fishing
Getting out on the water is a Charleston necessity, and with how great fishing is here, you should definitely hit the waterways with a seasoned captain. 4 Sons Charters local guides know the best near-shore and off-shore fishing spots for you and your crew, and they offer varying boats and experiences for your group's needs and size. And when you tell them Sweetgrass sent you, they’ll give you $50 OFF your in-shore fishing excursion!
Book a Tee Time at Turtle Point or the The Links Course
One of the best aspects of the Charleston Coast aside from our pristine beaches are our pristine fairways. Kiawah and Seabrook Island are known for their golf, while Wild Dunes and Isle of Palms boast some stunning greens right on the waterfront. It’s not a boys' weekend without booking a tee time, so we highly recommend getting ahead of the crowd and booking your golf excursion at Turtle Point on Kiawah Island or the Links Course within Wild Dunes, depending on where you’re staying.
Where to Eat
Fischer’s Pub at Bohicket Marina
If you’re staying on Kiawah or Seabrook Island, then Fischer’s Pub is a must stop for any guy looking for standout bar food paired with a good game of pool. Located in Bohicket Marina, Fischer’s is a local legend and the best spot to kick-off or wrap-on a guys’ weekend.
Henry’s On The Market
Another local favorite, Henry’s On The Market is the best catch-all establishment for good food, good drinks, good views and a good night out. With live music on two floors, rooftop views, and delicious drink options served all day and late into the evening, Henry’s is a great spot for a quick bite or an ideal night-out with friends in the heart of Downtown Charleston. No matter your intent, Henry’s is definitely worth a stop!
Your Local Charleston Experts
Sweetgrass Properties has served the Charleston region for over 30 years. Created and run by locals, our boutique vacation rental agency serves our community and small businesses by offering only the best when it comes to Charleston coast stays. Voted Best Vacation Rentals by Charleston Choice in 2025, Sweetgrass Properties is the company you want to go with when planning your next Charleston getaway.
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. Check out properties across islands like Kiawah, Seabrook, Isle of Palms, and Wild Dunes for your next vacation and experience the Sweetgrass difference