Vacation rentals in Callawassie Island

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Top-rated vacation rentals in Callawassie Island

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Top guest favorite

The charming cottage features a low country style exterior with reclaimed wood siding and a corrugated metal roof. A welcoming front porch is adorned with seating. Surrounding landscaping includes shrubs and trees, enhancing the serene setting within the historic district.

Home in Bluffton

4.99 out of 5 average rating, 384 reviews

Bluffton Farm Cottage: Come for Summer Vacation

(STR21-00116) Located in the Old Town Bluffton Historic District, our charming cottage is a short walk from art galleries, boutiques, gift shops, restaurants, parks, historic houses, and the May River. Hilton Head Island beaches and bike trails, dozens of golf courses, two National Wildlife Refuges, a variety of coastal/ocean opportunities, and many outdoor activities are nearby. Only 35 minutes from Savannah, the cottage is ideal place for couples trips, friends getaways, or family vacations.

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, 298 reviews

Lovely Cottage in Beaufort w/ State Park Beach Pas

This adorable but well-appointed farmhouse cottage is located just a few streets from the heart of DT Beaufort, in the desired neighborhood of Pigeon Point, with easy access to the boat launch. Just a few blocks from Bay Street 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).

Top guest favorite

A spacious bedroom features a large bed dressed in neutral linens, flanked by light wood nightstands with lamps. Natural light floods in through multiple windows and skylights. A cozy seating area with light-colored cushions and decorative pillows provides additional comfort.

Home in Bluffton

4.98 out of 5 average rating, 165 reviews

Old Town Bluffton Cottage + FREE Golf Cart!

Beautiful & newly renovated Cottage in the heart of Old Town Bluffton shopping & dining district. Located directly across the street is the Heyward house, and with all the restaurant, parks, & Church of the Cross within a block or 2 from the front door, our home is literally steps away from it all. The beautiful new Wright Family Park which is right on the water with shore access & Fishing just a 4 minute walk away. Our home is a hidden gem in Bluffton & we are happy to share it with you!

Top guest favorite

A bright living and dining area is presented with large windows allowing ample natural light. A white wooden table with four decorative chairs is set beside a cozy seating area featuring a green chair. A ceiling fan and chandelier enhance the inviting atmosphere.

Apartment in Bluffton

4.99 out of 5 average rating, 425 reviews

Guest House on Lawrence Street

UPDATED LUXURY & FASTIDOUS CLEANLINESS in one of historic OldTown Bluffton’s coziest carriage houses. OldTown’s vibe is just plain fun. Stroll to wide variety of super restaurants, night life, art galleries, boutiques, antebellum homes & lush waterfront parks on the idyllic May River. Built in 2018 w/ quartz counters, private bedroom w/ plush king-size bed, upscale bath w/ soaking tub, bright living/dining room, full kitchen w/ gas cooktop, romantic rocking-chair porch up in moss-draped oaks.

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, 520 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

4.96 out of 5 average rating, 654 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, 622 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 combined living and sleeping area features a gray couch with decorative pillows, a small coffee table, and a light-colored area rug. A twin bed with a white quilt and pillows is visible in the background, with large windows draped in yellow curtains allowing natural light to enter.

Guesthouse in Hilton Head Island

4.94 out of 5 average rating, 220 reviews

Alli B's Air B and B-Great Country access off 278

Your family will be close to everything when you stay at this centrally-located place. No gate fees or parking fees- right off of 278- central located between Bluffton and HHI under foot of bridge. Farm like experience -family owned 30 years . Quiet . Pet friendly . Beds-two twin -can pull together if wish -one couch(Not a sofa bed) and one mattress under a bed that can be moved out . Property has several buildings , Guest apt is above garage. NOTE: SEE Space info below

Top guest favorite

A living area features a comfortable sofa and stylish coffee table placed on a patterned rug. Natural light filters through the large window, illuminating the decor. A kitchenette with modern appliances is visible, along with sliding glass doors leading to an outdoor deck.

Apartment in Bluffton

5 out of 5 average rating, 143 reviews

Charming carriage house in Bluffton

Newly renovated carriage house close to everything Bluffton and Hilton Head have to offer. Less than a mile to the restaurants, shops, and galleries of historic Old Town Bluffton, 8 miles to Hilton Head Island, and just 18 miles to Savannah’s riverfront. Plush king-size bed, pull-out sofa, efficiency kitchen with microwave, refrigerator, coffee maker, and a large private deck are all available for guests. *Please note - minimum age of 10 for a child as the 3rd guest.

Top guest favorite

The entrance reveals a spacious living area, featuring a comfortable sofa and a piece of wall art depicting a sunset. The open-plan design connects to a well-equipped kitchen visible in the background, with light-colored walls and warm wood flooring enhancing the inviting atmosphere.

Guesthouse in Bluffton

4.93 out of 5 average rating, 285 reviews

Beautiful Carriage House! Your Home Away from Home

Looking for the perfect Bluffton stay? Our cozy carriage house is minutes from everything Bluffton has to offer! Located just 20 minutes from the beaches of Hilton Head Island, and a 20-minute walk (or 3-minute drive) to downtown Bluffton. Enjoy complete privacy with easy keypad entry, convenient on-site parking, in-unit washer and dryer, a spacious living room with a sofa bed, a fully equipped kitchen, and comfortable accommodations for up to 4 guests.

Guest favorite

A cozy outdoor area is highlighted by a gazebo with soft fabric drapes. Seating is provided by a sectional sofa and armchair, arranged around a low coffee table. A hammock hangs nearby on the manicured grass, enhancing the serene atmosphere.

Apartment in Bluffton

4.84 out of 5 average rating, 187 reviews

Bluffton Cottage • Fenced yard • Pet-Friendly

Located in the heart of downtown Bluffton. Just a short walk to the many shops, restaurants, & parks in Old Town. Newly remodeled cottage with fully stocked kitchen, smart TV, games, washer, dryer, king bed, & two pull out twin beds. Enjoy cozy outdoor area with gazebo, outdoor lounge, & hammack. A short drive to the beaches of Hilton Head, Savannah, &Beaufort or take a day trip to Charleston or even Jacksonville, FL. Pet friendly.

Top guest favorite

A cozy bedroom features a spacious bed with soft linens, accented by decorative pillows. A stylish wash basin is shown with toiletries on a wooden vanity. A living area showcases comfortable seating, decorative plants, and a coffee table, enhancing the welcoming environment.

Home in Port Royal

4.99 out of 5 average rating, 228 reviews

Great reviews! Stylish Port Royal cottage!

Bright and airy with an open floor plan, this quaint cottage boasts unique features and effortless style in 900 sq. ft. This stylish, newly renovated home is just minutes from Parris Island, historic downtown Beaufort, and a 20-minute scenic drive to Hunting Island-it's the ideal Lowcountry retreat. Port Royal, SC license# 12106