Vacation rentals in Callawassie Island

4.99 out of 5 average rating, 382 reviews

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

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.

4.89 out of 5 average rating, 235 reviews

A spacious studio features a comfortable king bed with bedside tables and lamps. A rattan chair is positioned nearby. The kitchenette, equipped with a black refrigerator and stove, complements the casual seating area. Natural light fills the room through a window with blinds.

Guesthouse in Bluffton

Your own carriage house - detached, private, safe!

Awesome carriage house in quiet, prestigious Bluffton community. Completely private, detached 300 sq ft space perfect for groups of 2 adults/child. Enjoy an open floor plan, 1 comfy king bed plu& thoughtful touches that make this the perfect home away from home. Close to everything you want to see - just 20 minutes to Savannah, Hilton Head or Beaufort. Restaurants, shopping, golf & beaches! Plus, we're happy to be your personal concierge and offer tips on everything the low country has to offer

Condo in Hilton Head Island

A wooden boardwalk leads through grassy dunes towards the beach. The path extends toward the calm ocean, under a gray sky. Soft sand is visible at the boardwalk's end, inviting guests to access the beachfront.

4.96 out of 5 average rating, 307 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo

Newly remodeled just last year! Adorable beach front condo located in HH Beach & Tennis Resort. Watch & listen to the ocean waves right from your 2nd floor balcony! The condo is in a gated area within where guests will have access to a private beach, 2 pools, resort restaurants, tennis, pickleball, beach volleyball, playgrounds, cookout areas, bike rental, and a gym. We also provide beach chairs, coolers, boogie boards and coffee! It's all here! The getaway you've been waiting for and deserve!

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.

4.99 out of 5 average rating, 423 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.

4.95 out of 5 average rating, 516 reviews

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

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!

4.96 out of 5 average rating, 120 reviews

The front exterior of the house features a welcoming porch with a central decorative door and flanking windows. Flowering plants are suspended from the eaves, while well-maintained shrubs frame the entrance. A clear pathway leads to the door, inviting guests into the home.

Home in Bluffton

Encanto of the Lowcountry in Old Town Bluffton

Welcome to the Heart of the Lowcountry - Bluffton South Carolina! Come stay in this vibrant & luxurious 2 BED / 2 BATH recently renovated home and enjoy the coastal way of life with cool river breezes as you discover the hub of businesses, shopping and community gatherings of eclectic Old Town. Spend time in the sun and sand on the nearby beaches of Hilton Head Island or visit the downtown waterfront of Historic Beaufort. Lots of local fun & activities! Welcome to Encanto of the Lowcountry.

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.

4.96 out of 5 average rating, 652 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.

5 out of 5 average rating, 617 reviews

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

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!

Guesthouse in Hilton Head Island

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.

4.93 out of 5 average rating, 213 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

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.

5 out of 5 average rating, 140 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.

4.92 out of 5 average rating, 279 reviews

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

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.

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.