Vacation rentals in Callawassie Island

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).

Value · Location · Laundry

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 !

Family · Value · Comfort

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!

Location · Value · Amenities

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!

Location · Family · Parking

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!

Value · Location · Sleep quality

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!

Location · Value · View

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!

Value · Family · View

Canopy House | Walk to Harbour Town | Marshfront

Canopy House is an artfully curated retreat in Sea Pines, nestled among live oaks and Spanish moss, where walls of floor-to-ceiling windows frame sweeping views of the tranquil salt marsh along the serpentine Heddy Gutter Creek. Walk or bike to Harbour Town for dining, live music, and shops, or spend the day at the beach. Return to a peaceful oasis where nature and design inspire meaningful moments together.

Location · Family · Walkability

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.

Family · Location · Access

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.

Value · Location · Decor

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.

Location · Family · River

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.

Outdoor spaces · Quiet · Hospitality