Vacation rentals in Callawassie Island

Beautiful Spacious Remodeled Private House w/Pool!

Low Country's Finest Accommodations ! Beautiful 4 bedroom 2 bath fully renovated property nestled on four secluded acres with a pool. The house is stunning and offers all the charm of Low Country living. Ideal for family gatherings, relaxing vacation, a quick getaway for fishing and golf. Centrally located with easy access to Callawassie Island ( 5 min) Beaufort ( 20 min ) Bluffton (20 min) Savanah (45 min) Hilton Head (45 min) Charleston (90 min ). Come enjoy your "Home away from Home !

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!

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!

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!

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!

1mi to MCRD PI | Pinky's Palace | Cozy Bungalow

This peaceful 2BR bungalow in Mossy Oaks is the perfect home base for Parris Island graduations, Port Royal visits, and Lowcountry getaways. Minutes from Parris Island, downtown Beaufort, Port Royal, beaches, and the Spanish Moss Trail, guests enjoy a stress-free stay with renovated interiors, Smart TVs in every room, a fully equipped kitchen, and relaxing outdoor spaces. Quiet, convenient, and family-friendly with true Southern charm.

Waterfront Tree House | HT Pool | Private Office

One of our newest homes, see our over 1000 *5*-star reviews. Calibogue Escape-Harbour Town Treehouse in Sea Pines Sailboats, Dolphins, Sunsets, what else could you ask for? This treehouse offers floor-to-ceiling windows with unparalleled views and the perfect setting for a perfect escape. Located on a dead-end street on Deer Island, just steps from Hilton Head’s Harbour Town and the Yacht Basin, this hideaway could not be more perfect.

The Love Bird Suite

Located on the serene and historic Wilmington Island, this space was designed as a romantic couple’s getaway. Enjoy this spacious studio, equipped with a working indoor gas fireplace, a large soaking tub, floor to wall tiled shower, and an outdoor hot tub. Centrally located between Historic Savannah and Tybee Island, enjoy day trips to visit these amazing places and return to a relaxing and romantic retreat style stay.

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.

Charming Bluffton Single Story Home In Old Town

Bask in the delight of Old Town from this freshly remodeled Bluffton home, whose airy aesthetic complements the riverside surroundings. Bright, breezy bedrooms and front porch seating or screened in porch dining provide ample comfort after exploring nearby landmarks. Located near beautiful pond that's great for seeing local wildlife such as deer, red fox, great blue heron, wood storks and lots more!

Low Country Home in Beautiful Habersham

This stunning Habersham home is the perfect blend of modern convenience and southern hospitality. With all the necessary furnishings and living tools, it's the ideal spot for both short and long-term stays. Relax on the traditional front porch, take in the charming small-town vibes of Habersham, and explore everything the beautiful South Carolina Low Country has to offer.

Heaven Island Lodge Daily Golf Included

Golfers’Paradise: Free Daily Golf + Comfortable Home. The property is on Callawassie Island and overlooks the 9th fairway of the Palmetto course and is close to Callawassie amenities including golf (two rounds per day included with the daily rental) clubhouse, tennis and pickle ball courts, two pools, kayaks, state of the art fitness center.