Cottage holiday rentals in Hilton Head

Old Town + Walk to restaurant + EV Charger

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

Fall Rates are GREAT! Spa only after November 1st

This is a honeymooners delight! Small families are welcome too. *During the winter months-the Heated Spa is available, but not the pool.* HEATED POOL/SPA OPTION IS $40.00 per DAY EXTRA. Charged at end of stay. YOU WILL BE CHARGED FOR THE ENTIRE STAY, UNLESS YOU LET ME KNOW THAT YOU DO NOT WANT THE HEAT FOR THE POOL/SPA FOR THE DAY. YOU MUST LET ME KNOW IN ADVANCE AND AT LEAST BY 7 AM OF THE DAY, THAT YOU DO NOT WANT THE HEAT TURNED ON. Per city code maximum number occupancy is 4 adults.

Shipyard! - Private Beach & Golf! Pet Friendly!

This 2 bed 2.5 bath cottage features access to great community amenities including private beach access and the Shipyard beach club. Within the Shipyard gates, enjoy 27 holes of championship golf courses, biking trails, restaurants, bars, spas, and the Sonesta Resort. Dozens of restaurants offering up Hilton Head Island's famous local seafood, craft beer, and "The Bank" are a stones throw away. Shopping and site seeing are a walk or bike-ride away at Coligny Plaza and Celebration Park.

Couples Retreat | FREE Golf Cart/Bikes/Kayaks+Dock

Welcome to Siren & Seafarer Cottage! Immerse yourself in all that Tybee Island offers w/ FREE kayaks, bikes and an electric golf cart. Unwind in this luxurious getaway & nature-lovers paradise. Relax on your private dock w/ a cozy swing bed while surrounded by amazing panoramic views of the tidal creek & marshlands. Nestled amongst enchanting live oaks & marsh-side scenery, you'll soon discover something inherently romantic about this cozy historic cottage ~ book now and fall in love!

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.

Beach City @ Freedom Park

Welcome to Beach City @ Freedom Park This gorgeous new build comes fully stocked with everything you could possibly need for your best beach vacay ever! 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 or amount of amenities: grills, bikes are self service unless purchased butler service, clutter, paper products, washcloths

Bluffton Retreat, Pets Welcome.

Located in a quiet neighborhood, minutes walk from Old Town Bluffton. You can find unique shops, art galleries, and several great restaurants. In short 10 minute drive you will be in Hilton Head Island, where there is so much to do and explore! Savannah, GA is about 30 minutes away. Our home offers keyless entry, a great outdoor kitchen, and a king size bed . All this and more, come spend a special time with your loved ones and pets here in Bluffton!

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.

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

Only 200 Yards From The Beach ! Ocean View !

Within 200yds of Beach, renters will have the pleasure of staying in a Beautiful Home. Daufuskie Island is unique in that it does not have a bridge. Visitors, renters and owners travel from Hilton Head or from Savannah by Ferry to the Island. We will help. There is something about a charming beach cottage that is irresistible.