Holiday rentals in Callawassie Island

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Top-rated holiday rentals in Callawassie Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

Flat in Bluffton

4.99 out of 5 average rating, 476 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!

FamilyValueSleep quality

Top guest favourite

The image captures a private heated pool beneath a covered patio. Comfortable lounge chairs surround the pool, and an outdoor dining area features a large table with chairs. A shaded umbrella stands above the table, while greenery and a grill are visible, enhancing the outdoor setting.

Home in Hilton Head Island

5.0 out of 5 average rating, 123 reviews

98 Sandcastle Ct

98 Sandcastle Ct Brand New 6 Bedroom Home near Beach with Pool, Elevator/ (Sleeps Up To 22 Guests ) 20 in beds & 2 in Queen Sofa Sleeper. Over 3200 sq feet, 6 Bedrooms, Heated Pool, Elevator & about .3 miles from the beach = Tons of Fun!!! * 6 Bedrooms * 4 Full Baths * Walking Distance to Ocean. * Heated Private Pool. (Free pool Heat :) * Elevator Available: Free use Adults Only. * Free Parking: 4-6 reg cars/mini vans.. LRG SUV's or LRG Vans = 4 parking spots. Note: 2 = garage 4 =driveway.

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Top guest favourite

A serene bedroom is presented with a light color palette. A spacious bed adorned with soft blue pillows is positioned in front of a large window with white blinds. A wooden bench sits at the foot of the bed, featuring neatly arranged towels. A side table with lamps and a decorative piece enhances the inviting space.

Home in Bluffton

4.99 out of 5 average rating, 265 reviews

Old Town Bluffton Home + Golf Cart No Cleaning Fee

This is Bluffton Living at its finest! This luxurious southern coastal home is located in the heart of Old Town Bluffton just a couple blocks from the Promenade & includes a new Golf Cart at no additional charge. Master is on the main floor. Walking distance to wonderful local hot spots including the coffee shops, wine bar, high end/casual restaurants, and charming boutiques. Our home has it all w/ a full kitchen w/ stainless steel appliances, Traeger grill, dishwasher, washer/dryer, & More!

LocationValueBeach

Top guest favourite

The front exterior of the home features a welcoming porch with blue shutters and a vibrant blue door. Neatly trimmed hedges surround the entryway, and a paved pathway leads to the entrance. Lush green grass and a bright sky enhance the inviting curb appeal.

Townhouse in Bluffton

4.95 out of 5 average rating, 249 reviews

Newly Remodeled Lowcountry Escape!

This will be our third Airbnb in this community as we love it so much! The home is two bed and two full bath. A lovely single story home that is ADA friendly equipped with a ramp in the back and wheelchair width doors throughout. Conveniently located a short drive from many beaches or downtown Savannah. Within walking distance of downtown Bluffton with tons of awesome galleries, fun shops and amazing food! We have superhost status and strive to ensure your stay is comfortable and enjyable!

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Top guest favourite

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.

Guest house in Bluffton

4.99 out of 5 average rating, 714 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!

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Top guest favourite

A tranquil waterfront view is captured at sunset, showcasing vibrant hues of pink and orange reflected across the water. Silhouetted against the sky are tall grasses by the dock, creating a peaceful atmosphere. The scene is framed by a white picket fence.

Guest house in Beaufort

4.95 out of 5 average rating, 356 reviews

River Retreat- Waterfront- Less than1 MI from PI

Escape to your own peaceful waterfront retreat less than a mile from Parris Island! This 3-bedroom, 2-bath river guest home sleeps up to 8 and features breathtaking water views, a private deep-water dock, screened porch, full kitchen, and washer/dryer. Watch the sunrise over the river, fish from the property, keep an eye out for feeding dolphins, or simply relax by the water. Perfect for Marine Corps graduation families, boating and fishing trips, or a relaxing Lowcountry getaway.

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Top guest favourite

Townhouse in Okatie

4.94 out of 5 average rating, 32 reviews

Perfect for golf escapes, military families, or nearby family gatherings! • 2 Complimentary Rounds of Championship golf per day ($250 day value) • Free bike rentals • 3BR/2BA on beautiful Callawassie Island • Sleeps 6 with king, queen, and twins • 2 heated/cooled pools, tennis, and pickleball • 2 on-site restaurants • <30 mins to Beaufort • 30 mins to Bluffton & Parris Island • <60 mins to Hilton Head & Savannah • <90 mins to Charleston Discover charm, luxury, and adventure

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Top guest favourite

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, 483 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.

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Top guest favourite

Cottage in Saint Helena Island

4.98 out of 5 average rating, 145 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.

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Guest favourite

A charming house is set back from a winding driveway, characterized by a front porch adorned with hanging plants. Lush greenery and manicured landscaping complement the welcoming entrance, while the sloped roof adds to the home's inviting character.

Home in Beaufort

4.93 out of 5 average rating, 362 reviews

Tabby House, Parris Island, Reunions & Beaches

Close to Parris Island, a lovely Lowcountry home with 6 spacious bedrooms at the end of a quiet street. Ideal for large family gatherings. A very clean, comfortable, & welcoming environment. Great location 4 miles to historic downtown Beaufort on the waterfront where you will find plenty of restaurants and shopping. A few miles from the new Spanish Moss Trail and a boat launch in nearby Port Royal.

ValueLocationOutdoor spaces

Guest favourite

Home in Bluffton

4.85 out of 5 average rating, 265 reviews

Bluffton/Hilton Head Island/Savannah Vacation Home

A 3 great bedroom house in Bluffton SC.Full kitchen, Spacious master bedroom, walk in closet, fire stick streaming tv, Big backyard with private fence. There is 1 kingsize bed, two queen beds. There is a propane gas grill in the backyard, a public pool is a walking distance away. The house is minutes away from Bluffton Old Town , 11 miles away from Hilton Head Island heading to the beaches.

LocationFamilyQuiet

Guest favourite

The villa is set within a lush landscape, featuring a two-story design with a welcoming front porch. Leafy trees provide shade around the well-kept gardens, and a driveway leads to the attached garage, creating an inviting entrance for guests.

Home in Okatie

4.87 out of 5 average rating, 46 reviews

Free Daily Golf Villa · Private Island · 4BR/4BA

Wake up on a private, gated island where your stay includes a round of championship golf EVERY day. Our 4BR/4BA waterfront villa, renovated 2026, has an en-suite bath in every bedroom, sleeps 9, and is dog-friendly. Heated pools, hot tub, tennis, pickleball, spa, and docks included, 25 min from Hilton Head. Monthly snowbird rates available, just ask.

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