Holiday rentals in Callawassie Island

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!

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!

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!

Newly Remodeled Lowcountry Escape!

This will be our third Airbnb in this community as we love it so much! The home is two bed and two full bath. A lovely single story home that is ADA friendly equipped with a ramp in the back and wheelchair width doors throughout. Conveniently located a short drive from many beaches or downtown Savannah. Within walking distance of downtown Bluffton with tons of awesome galleries, fun shops and amazing food! We have superhost status and strive to ensure your stay is comfortable and enjyable!

Ocean Overlook - The Ultimate Vacation Experience

LUXURIOUS, DIRECT, OCEANFRONT HOME! UNOBSTRUCTED OCEAN VIEWS! SO CLOSE YOU CAN HEAR THE WAVES CRASH WITH THE WINDOWS CLOSED! DIRECT BEACH ACCESS! POOL ACCESS! ALL BRAND NEW! 3RD FLOOR! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM! WATCH EVERY SUNRISE & SUNSET! KING BED! CAN SLEEP 4! THIS IS LUXURY LIVING WITH NO RESORT AMENITY CHARGES! SAVE THOUSANDS OF DOLLARS COMPARED TO OTHER NAMED RESORTS LUXURY HOTEL PROPERTIES! **UPGRADED INTERNET & HD TV PACKAGE + FREE AMENITIES**

Luxury Promenade Townhouse in Old Town Bluffton

Experience upscale Lowcountry living in the heart of Old Town Bluffton. This elegant yet inviting townhouse in the Promenade puts you steps from gourmet dining, boutique wine bars, art galleries, and charming cafés. Enjoy an open, well-equipped kitchen and bright entertaining space, or sip cocktails on the porch overlooking lively Promenade Street where the sound of live music drifts through the evening air. Southern charm and sophistication meet for the perfect Bluffton getaway.

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.

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.

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.