Vacation rentals in Callawassie Island

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Top-rated vacation rentals in Callawassie Island

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Top guest favorite
A charming A-frame structure is elevated on a wooden deck, surrounded by lush foliage. The entrance features a white door framed by large windows, allowing natural light to illuminate the space. A small staircase leads to the inviting porch with bright yellow chairs.
Treehouse in Saint Helena Island
4.99 out of 5 average rating, 158 reviews

"A" Secluded Quiet Oasis w/ Beach Pass

Detox You'll love this unique and romantic escape. Architectual design allows you to fully take in the view of the lowcountry marsh. The backdrop of the bed allows you to fall asleep to the majestic starry filled night sky! Soak your cares away with a bath that will surely relax and unwind you. The background is breathtaking! The outside shower allows you to take in the scenery while enjoying a hot shower. This is an "unplug" listing, no tv or internet access. Hunting Island Beach Pass included.

Top guest favorite
A spacious studio apartment is shown, featuring a king size bed draped in a patterned quilt. A dresser and lamp are positioned nearby, while a modern kitchen area is visible in the background. Natural light fills the room, highlighting the warm wooden flooring.
Apartment in Bluffton
4.99 out of 5 average rating, 208 reviews

Sunset on the May / Historic Old Town Bluffton

Spacious studio apartment sits above a detached garage with your own private entrance located in the heart of Old Town Bluffton. A short stroll to nearby restaurants, boutiques and unbelievable sunsets on May River. New king size bed, appliances and large sectional couch. Full kitchen with plenty of space to relax and store your things. Nice size bathroom, full shower and an abundance of amenities like private fire pit, outdoor grill and patio table for your enjoyment. HH Beaches minutes away!

Top guest favorite
A charming cottage is set amidst lush greenery, featuring a wide, welcoming pathway made of patterned pavers leading to a spacious deck. Large windows reflect natural light, and a few outdoor chairs are positioned under umbrellas, inviting relaxation in the shaded area.
Cottage in Beaufort
4.98 out of 5 average rating, 189 reviews

Private Island Cottage

Looking for a place to relax and enjoy a stress free holiday, consider this Beautiful cottage set on a private Island with dock access to the intercoastal water way. Minutes from downtown Beaufort, 35 miles from Hilton Head Island, 45 miles from Savannah, GA, 60 miles from Charelston. only minutes from great resturants and attractions like: Hunting Island state park and public golf coures. Fishing, kayaking or paddel boarding (equipment provided), or just relax on one of the docks or porches.

Top guest favorite
Apartment in Bluffton
4.99 out of 5 average rating, 453 reviews

Guest House on Lawrence Street

UPDATED LUXURY, FASTIDIOUS CLEANLINESS in historic OldTown Bluffton’s coziest carriage house. OldTown’s vibe is just plain fun. Stoll 2 blocks to super restaurants, night life, art galleries, boutiques, antebellum homes & lush waterfront parks on the idyllic May River. New in 2018 w/ quartz counters, private bedroom w/ plush king-size bed, upscale bath w/ soaking tub, bright living/dining room, full kitchen & romantic rocking-chair porch up in moss-draped oaks. Read our Reviews—guests love it!

Top guest favorite
A wooden staircase descends towards a dock on serene waters, framed by tall grasses. A blue roofed structure is positioned at the water's edge, with boats visible nearby. The sky is partly cloudy, reflecting natural light onto the calm surface.
Home in Beaufort
4.96 out of 5 average rating, 103 reviews

Belle Monte (beautiful mountain) on the water!

Belle Monte is a lovely light-filled 2 story home on high bluff overlooking Middle Creek off the Whale Branch river in Beaufort, SC. See gorgeous sunrises & watch the dolphins from the upstairs deck or sun porch. Great views of the water from most of the house. New lighted dock on deep water so bring your boat! Enjoy swimming (ladder provided), kayaking or paddle boarding. Great area for fishing and crabbing. Well-equipped kitchen, fireplace, gas grill, screened-in porch, game table & more!

Top guest favorite
A private screened-in dock features a swing bed adorned with decorative pillows, offering a cozy resting space. Ambient Edison lights create a warm glow, while views of the marshland are visible through wooden frames and open spaces.
Cottage in Tybee Island
4.99 out of 5 average rating, 184 reviews

Private Dock | FREE Golf Cart | Kayaks | Bikes

Welcome to Siren & Seafarer Cottage! Immerse yourself in all that Tybee Island offers with your own FREE GOLF CART, BIKES, & KAYAKS. Pamper yourself with this luxurious getaway and nature-lover's paradise. Relax on your PRIVATE DOCK on a cozy swing bed while surrounded by panoramic views of the tidal creek. Nestled amongst enchanting live oaks and marsh-side scenery, you'll soon discover something inherently romantic about this Tybee Island cottage, just 25 minutes to downtown Savannah.

Top guest favorite
The cottage features a modern design with a sloped roof and expansive glass walls that create a bright and open feel. A wooden deck wraps around the front, complemented by a pergola and greenery, inviting relaxation in the tranquil outdoor space.
Cottage in Hardeeville
4.95 out of 5 average rating, 550 reviews

Tranquil Savannah River Cottage w/ Views+Breakfast

Awaken on the banks of the Savannah River w/ views, song birds & morning coffee! Enjoy the 2x decks, full wall glass doors, metal roof rain, 2 acres strung w/ Spanish moss & relaxing in the sun as the water hits the docks! Bring a book, fish, or hike! Enjoy breakfast, gas BBQ, firepit, screened porch+fans, fast wifi & SmartTV! 2023 renovated & travel magazine featured! Near Savannah, Hilton Head, I95 & airport! This adorable, smaller cottage is perfect for special occasions or getting away!

Top guest favorite
A three-story building is depicted, featuring a light-colored exterior with a spacious porch adorned with white railings. The ground level showcases large windows and a welcoming entrance. Stairs on the side lead to the upper levels, framed by greenery in the background.
Apartment in Bluffton
4.97 out of 5 average rating, 693 reviews

Bluffton Villa in the heart of the Promenade

Beautiful villa in the heart of the Promenade in the Historic District of Bluffton. Steps away are a wine bar, coffee shop, French bakery, 5 star and casual dining, & fabulous boutique shopping. Newly built in 2017, we offer our guests a fully equipped kitchen with an electric convection oven, microwave, dishwasher, ice maker in refrigerator. The bathroom offers a large walk in shower with a rain shower head, and the bedroom has a King size bed. You are a 15 minute ride to Hilton Head.

Top guest favorite
A well-lit living area features a comfortable sofa and a patterned armchair, surrounded by large windows allowing natural light. A coffee table holds magazines and a decorative tray, while plants add a touch of greenery. The kitchenette is visible in the background, enhancing the open layout.
Guesthouse in Bluffton
4.99 out of 5 average rating, 685 reviews

Lowcountry Retreat Carriage House

Located in a quiet neighborhood, minutes from Old Town Bluffton, where you can find unique shops, art galleries, & great places to eat - many with live music! A stroll through the neighborhood will take you past a local park with playground, workout area, & walking paths. There are many ponds to enjoy the local wildlife, wetland areas, and beautiful oak trees. It's so peaceful! Convenient to Hilton Head, Beaufort, and Savannah, it's the perfect spot for exploring, shopping, or relaxing!

Top guest favorite
A serene outdoor setting features a cozy fire pit with firewood arranged inside. Two turquoise Adirondack chairs are positioned nearby, inviting relaxation. A winding stone path leads to a charming house with a spacious porch, surrounded by lush greenery and Spanish moss-draped trees.
Cottage in Beaufort
4.97 out of 5 average rating, 203 reviews

Peaceful River Retreat Near Historic District

This tranquil, private, river retreat has incredible views of the marsh and the Beaufort River. Located in popular Pigeon Point, you are just a short bike ride or a 20 minute walk to the historic district and downtown Beaufort. I also have another more glamorous and exotic property next door see it at: airbnb.com/h/motm Enjoy fishing and crabbing right in your back yard at high tide or take a short walk down to the boat landing where you can watch people hand cast nets for shrimp!

Top guest favorite
A charming white cabin is set amidst lush greenery and flowering plants, featuring a welcoming front porch with steps leading to the entrance. Spanish moss hangs gracefully from nearby trees, enhancing the serene atmosphere of the outdoor space.
Bungalow in Bluffton
4.99 out of 5 average rating, 474 reviews

Bluffton's Historic Guest House

LOCATION! Charming cabin built c. 1910 with antiques and vintage decor provides in miniature all you need for a quiet getaway weekend with superb viewing & swimming from the dock or a month of blissful exploration of the Lowcountry. Walk to Old Town galleries, shops, 21 restaurants & festivals mixed with Farmer's Market on Thursdays 1-6 PM within one mile. Local seafood to cook available only four blocks away.

Top guest favorite
Cottage in Saint Helena Island
4.99 out of 5 average rating, 125 reviews

Private Waterfront Retreat w/ Sauna

Escape to The Hideaway, a newly built modern 2BR/2BA waterfront retreat on St. Helena Island. Surrounded by live oaks and sweeping salt marsh views, this architecturally unique cottage blends luxury and nature with curated amenities, including a private indoor sauna. Peaceful and secluded, yet just minutes from beaches, outdoor adventures, local shops, and dining—designed for rest, reconnection, and renewal.

Popular amenities for Callawassie Island vacation rentals