Cottage holiday rentals in Hilton Head

4.99 out of 5 average rating, 172 reviews

A private screened-in dock features a swing bed adorned with decorative pillows, offering a cozy resting space. Ambient Edison lights create a warm glow, while views of the marshland are visible through wooden frames and open spaces.

Cottage in Tybee Island

FREE Golf Cart/Dock/Kayaks/Bikes, Couples Retreat

Welcome to Siren & Seafarer Cottage! Immerse yourself in all that Tybee Island offers with your own FREE GOLF CART, BIKES, & KAYAKS. Pamper yourself with this luxurious getaway & nature-lovers paradise. Relax on your PRIVATE DOCK on 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!

The exterior of the carriage home is visible, showcasing a two-story structure with white siding and a metal roof. Stairs lead up to a covered entrance, and outdoor string lights are strung along the eaves, creating a welcoming ambiance. Surrounding greenery adds a peaceful natural backdrop.

4.97 out of 5 average rating, 153 reviews

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

4.86 out of 5 average rating, 403 reviews

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.

The front exterior of the cottage features a small covered porch with comfortable seating and a welcome sign. A well-maintained lawn is visible, providing a green contrast to the gravel driveway. Surrounding foliage adds a touch of natural beauty to the entrance.

4.82 out of 5 average rating, 157 reviews

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

Cottage in Saint Helena Island

The living area features a comfortable sectional sofa, accented by decorative pillows. A wooden dining table is set nearby, surrounded by tasteful artwork on the walls. Exposed wooden beams enhance the ceiling, and natural light filters through multiple windows.

5 out of 5 average rating, 256 reviews

Harbor River Cottage

Romantic cottage on three-acres surrounded by gorgeous South Carolina waterways with endless views on all sides! Cottage is dog-friendly, has a fully-fenced front yard and screened-in porch. Full kitchen, private parking, washer & dryer, 55" TV with DirecTV. A short 10 minute drive from Hunting Island State Park, and 20 minutes to Downtown Beaufort and all the major attractions. Cottage is beautifully furnished with custom pieces to make this your ultimate low country luxury getaway!

The exterior of the cottage is depicted, showcasing a two-story design with light-colored siding, surrounded by landscaped shrubs and greenery. A pathway leads to the entrance, flanked by a wooden railing, inviting access to the home.

4.92 out of 5 average rating, 125 reviews

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.

A two-story house is shown with a yellow exterior and a wide deck featuring two red umbrellas. The space underneath the deck is open, with parking for vehicles visible on a concrete driveway surrounded by green grass and landscaped areas.

4.97 out of 5 average rating, 108 reviews

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.

A new two-story house features a blue exterior with white trim, complemented by a spacious driveway. Lush green grass surrounds the home, with low shrubs and trees providing shade and privacy. The garage doors are visible, adding to the house's functional appeal.

4.93 out of 5 average rating, 103 reviews

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

4.94 out of 5 average rating, 371 reviews

A bright living area features a light-colored sofa and armchair adorned with decorative pillows. A white coffee table sits in the center, with a blue decorative object on top. Natural light fills the space through the window, and a ceiling fan adds to the airy feel.

Cottage in Tybee Island

Blue Star Beach Shack

Located mid-island, convenient to everything. Less than 5 minute walk to the Beach! This is an iconic 1940 "Tybee Island Beach House" built in an elevated style that is a typical architectural vernacular to Tybee. Original detailing abounds throughout with a perfect mix of old and new to create a super cozy, beachy vibe. Bright, light, and airy cottage with crisp white and navy accents throughout create a chic Low Country vibe while retaining the essence of a typical beach shack.

A charming two-story house is set against a backdrop of trees, featuring large windows that allow natural light to fill the interior. A welcoming front porch is highlighted by white rocking chairs, and a fenced yard offers a sense of privacy. Additional structures are visible in the background.

4.83 out of 5 average rating, 291 reviews

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!

4.97 out of 5 average rating, 114 reviews

A spacious living area features a blue sectional sofa positioned on a soft area rug. Bright artwork decorates the walls, complemented by natural light streaming through large windows. A coffee table sits in front of the sofa, with a television mounted on the wall, and a dining area visible in the background.

Cottage in Tybee Island

Whimsical, 1940s Cottage 4 blocks to the Ocean!

Kick back and relax in this calm, stylish space. Peaceful setting and super quiet neighborhood. Enjoy my amazing slice of heaven! Private, whimsical, side patio with charcoal grill, great front porch, and super quiet area. Yet, only 4 blocks to the beach & back river for incredible sunsets and 8 blocks to the downtown district and peir. This is a house split in half, so locked doors between you but noise consideration is appreciated!

An inviting open living space features exposed pine walls and floors, accentuated by a centrally placed sofa with decorative cushions. A cozy armchair and a circular metallic coffee table complement the layout. Sunlight filters through the shuttered windows, highlighting the warm tones of the room.