Vacation rentals in Callawassie Island

Bailey's Landing Deepwater Oasis

Enjoy your Lowcountry getaway at this stunning waterfront property. There are two separate buildings, which sleep up to 12 people. The main cottage has 2 bedrooms and a full bathroom. The guest cottage has 4 bedrooms, 2 full bathrooms, a wet bar, and laundry. Entertain family on the bluff and create cherished memories with days on the water. A spacious enclosed porch overlooking the Okatie River invites you to relax. Enjoy morning coffee, al fresco dining, or stargazing in this idyllic setting.

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!

Oceanfront KING BED 65"TV Beach Bar Pickleball GYM

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Beachfront Balcony Watch Sunrise/Hear Waves 1 min to Beach Boardwalk! Beachfront Pool, Tiki Bar & Grille FREE Pickleball, Tennis & Gym HGTV Designer Renovation Two 65" SmartTVs KING BED Expanded Bedroom Blackout Sleeping Marble Spa Bath Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Beach Bar/Sports Bar Gated 24/7 Security Seasonal Island Trolley Stop

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!

The Cottage at Burroughs

The Cottage at Burroughs has recently been completely renovated. A short walk or bike ride to downtown Beaufort restaurants and shopping, it is also just steps away from the Spanish Moss Trail and a short drive to Parris Island. The Cottage has space to park your boat trailer and is one mile from the Downtown Marina and boat landing. A scenic drive through our barrier islands will take you to the beautiful beaches and trails at Hunting Island State Park - complimentary guest pass provided.

Buddy's Cottage near everything in Beaufort, SC

Who is Buddy? He was our black Labrador of 12 years. This well kept tiny home is adjacent to our main home and is private. It has 1 bedroom, 1 full bathroom, a sleeper sofa , 2 TV's, a full kitchen and all the amenities of home. Downtown Beaufort is 2 miles away, Parris Island is less than 5 miles away. In a quiet neighborhood. Are coming for a fishing trip and bringing your boat? Come stay with us , we have room for your boat. You can flush your engine and rinse your boat down.

Cozy Carriage House Under Oaks | Old Town Bluffton

nook - /nʊk/ – a secluded or sheltered place or part. We welcome you to The Nook, a peaceful escape nestled beneath centuries-old oak trees and located steps away from the vibrant core of the Old Town Bluffton Historic District. Spend your days strolling tree-lined streets, dining at some of the Lowcountry’s best restaurants, and enjoying scenic parks overlooking the beautiful May River. Begin and end your day at your restful, coastal retreat.

Sunset Serenity - Luxury on The Lagoon!

LUXURIOUS, SPACIOUS, ONE-OF-A-KIND RESORT HOME! CLOSE TO THE BEACH! CORNER VILLA! POOL ACCESS! LARGEST LAGOON VIEW IN THE RESORT! PRIVATE DECK! ENJOY MILLION DOLLAR SUNSETS! WATCH THE WILDLIFE PLAY! FIVE FOOT CUSTOM COFFEE BAR! KING BED IN MASTER! QUEEN & TWIN IN GUEST BEDROOM! XBOX! NETFLIX! THIS IS LUXURY LIVING WITH RESORT AMENITIES CLOSE BY! SAVE THOUSANDS OF DOLLARS COMPARED TO OTHER RESORT LUXURY HOTEL PROPERTIES!

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.

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.

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.