Vacation rentals in Callawassie Island

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Top-rated vacation rentals in Callawassie Island

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

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Top guest favorite

A charming farmhouse cottage is showcased, featuring a welcoming porch with rocking chairs. Lush plants are positioned on either side of the entrance, which is highlighted by a wooden door and decorative lighting. A well-maintained lawn contributes to the inviting exterior.

Cottage in Beaufort

4.98 out of 5 average rating, 336 reviews

Pigeon Point Cottage w/ State Park Beach Pass

This adorable, but well-appointed farmhouse Cottage is just a few streets from downtown Beaufort, in the quiet neighborhood of Pigeon Point. Easy access to a boat launch and walking distance to the park. A 30 minute walk to Bay St. and the Marina, where great shopping and outdoor dining with breathtaking views of the harbor await. A relaxed and inviting space, style, and beauty combine to make this special Cottage a much sought-after resting space for a memorable vacation with your loved one(s).

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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, 230 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!

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Top guest favorite

Townhouse in Okatie

4.93 out of 5 average rating, 30 reviews

Lux|Free Golf|Heated Pools|Free Bikes|Parris Is

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 all in one place!

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Top guest favorite

Apartment in Bluffton

4.99 out of 5 average rating, 474 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!

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Top guest favorite

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, 260 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!

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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

4.95 out of 5 average rating, 111 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!

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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, 206 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.

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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, 725 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.

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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, 709 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 favorite

Cottage in Saint Helena Island

4.98 out of 5 average rating, 142 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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Top guest favorite

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.

Guesthouse in Beaufort

4.95 out of 5 average rating, 350 reviews

River Retreat- Waterfront- 1 MI from Parris Islan

This river retreat can sleep 8 and is a little slice of heaven less than a mile from Parris Island. You will have the chance to hopefully see the dolphins feed while you are relaxing or you can sit on the porch and catch a breathtaking sunrise over the water. This is a quiet guest home that has amazing views whether you are coming for a graduation, to relax or enjoy the water this is the spot for you.

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Guest favorite

Home in Bluffton

4.86 out of 5 average rating, 260 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.

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