Cottage holiday rentals in Hilton Head Island

Old Town Bluffton! Walk to restaurants, Location!

Experience the ultimate retreat in the heart of Old Town Bluffton with our breathtaking carriage home. Wake up to the soothing sights and sounds of the nearby May River, enveloped in the refreshing scent of fresh water. This exquisitely designed one-bedroom sanctuary features a luxurious king-size bed, a full bath, a convenient washer/dryer, and a fully equipped kitchen. Conveniently nestled in the heart of Old Town Bluffton, our carriage home offers unrivaled proximity to an array of attractio

Gypsy Sea Cottage - A Beachside Retreat

Welcome to The Gypsy Sea Cottage—a beautifully renovated stand alone villa nestled in the prestigious Palmetto Dunes Resort, within the serene Queens Grant community. Just a short stroll to pristine beaches, championship golf courses, and world-class dining, this retreat offers a perfect balance of relaxation and adventure. Inside, you'll find high-end furnishings, luxury linens, smart home features, and a well-equipped kitchen—every detail thoughtfully designed for a seamless, memorable stay.

Old town Bluffton Charm, Best Location Calhoun St.

This charming cottage is in the heart of it all. Close to family-friendly activities and nightlife, located on the main street of Bluffton SC. Park and walk to restaurants, shops, bars and galleries. Located in the heart of Bluffton, 2 blocks to the town dock and the famous Church of the Cross. You’ll love my place because of the light, the comfy beds and coziness. We are pet-friendly, accommodate all types of guests and always professionally cleaned. Telsa charging station available

The Cucumber Cabana: Sleeps 2 adults + extra lofts

Welcome to the whimsical wonderland of the Cucumber Cabana; paradise tucked away in the enchanting woods under a canopy on Daufuskie Island! This cozy abode is big on charm and quirky delights. Featuring a main floor Queen bedroom and 2 additional lofts. With nature as your neighbor and a sprinkle of whimsy in every nook, the Cucumber Cabana promises a getaway that's as refreshing and quirky leaving you as cool as a cucumber! Book in conjunction with The Sol Shack next door to sleep 6!

Burkes Beach House - 2nd Row to Beach

Our home is second row at Burkes Beach. Close to Palmetto Dunes Plantation Golf and Tennis , Port Royal Plantation Golf and Tennis. Convenient mid Island location. It is great for couples, solo adventurists, and families (not set up for toddlers and younger). Steps to the beach path and Chaplin Park, which has lit tennis courts, park and picnic areas. Walk or bike on beach to Coco's Beach Bar or Marriott Beach Bar. Open floor plan and under house parking. OWNER IS A LICENSED REALTOR.

The Blue Heron @ Coligny Circle

Welcome to the Blue Heron! .This cozy little beach house is big on outdoor space. Wrap around decking is as large as the home itself! It is two Beautiful blocks to a public beach access and six blocks to Coligny Circle. The house is located on an island.100% refunds for Category 2 storms or higher. Otherwise, cancellation policy holds. Host is only responsible to access of property from I-95. Also cannot guarantee condition of amenities: grills, bikes, clutter etc.

The Oyster Cottage on Daufuskie w/ Golf Cart

A charming historic 3bd/1.5bath cottage that boasts authentic Daufuskie character with all the modern amenities. Located in the Historic district of the island, this cottage is nestled on a large piece of property next door to the Iron Fish Gallery, only a 5 minute walk to the Island Shack. Featured in Southern & Coastal Living, this retreat is perfect for a small group or family to escape and enjoy the serenity and quiet of the island.

New Cottage: 4th row & fully fenced back yard!

Enjoy your stay at this newly renovated Duplex (Entire First Floor), located in one of the most quiet and peaceful neighborhoods on HHI. 2 minute walk to the Beach! When your not soaking up the sun on the beach, relax in the open concept home with custom coastal finishes. Every room is equipped with a large smart TV and 1gig internet speeds. Spacious backyard with a privacy fence, grill, and outdoor furniture. Pets welcome!

Old Towne Bluffton Cottage

The Chic Bluffton Cottage is a one bedroom, one bath unique home in the heart of Old Town Bluffton. The unique all natural pine cottage has an open living space that offers a full kitchen.. The home has a very natural pine smell with walls and floors completely authentic. The home is walking distance to all shopping and restaurants