House holiday rentals in Hilton Head Island

Bluffton Farm Cottage: Come for Summer Vacation

(STR21-00116) Located in the Old Town Bluffton Historic District, our charming cottage is a short walk from art galleries, boutiques, gift shops, restaurants, parks, historic houses, and the May River. Hilton Head Island beaches and bike trails, dozens of golf courses, two National Wildlife Refuges, a variety of coastal/ocean opportunities, and many outdoor activities are nearby. Only 35 minutes from Savannah, the cottage is ideal place for couples trips, friends getaways, or family vacations.

Sea Pines hut, 5-min walk to beach, dog friendly!

Location; location; location! Awaken your senses in this cottage surrounded by natural beauty of pines, pond, and blue herons. 5 min walk to Sea Pines pristine beach. 2-mile bike to the beach club and Nature Reserve full of wildlife. Luxurious interior and cozy outdoor porch, plush king bed, queen sofa bed sleep 4. cathedral ceiling, dog friendly, free bikes, beach chairs and cart, perfect for couples, solo travelers, or small families looking to create a luxurious Hilton Head Island experience.

Modern Beach Escape | Private Pool~Steps to Beach

Welcome to your private slice of Hilton Head paradise—completely rebuilt and just steps from the sand. This 4BR, 3.5BA showstopper sits on a corner lot, 30ft from a private beach path. Enjoy the tropical pool area, fire pit, outdoor shower, and a massive balcony overlooking this beachside oasis. Inside: two stylish living areas, Smart TVs in every room, & luxe finishes throughout. Sleeps 11 & dog friendly. Minutes from top-tier golf, dining, & endless island adventures—book your dream stay now!

“Sea La Vie” 3BR, Sea Pines, Walk to Dining, Shops

Privately-owned 2000 SF one-level home sits on a wooded corner lot conveniently located inside the entrance of Sea Pines Resort. This 3 BR, 2BA home was extensively renovated in August 2020, with inviting French-inspired coastal decor for a relaxing cozy feel. "Sea La Vie" chalet is within walking distance to grocery stores, shops, and restaurants. A short drive or bike ride takes you to the private Beach Club, housing oceanfront dining and bar, upscale facilities, and wide beaches. Bienvenue!

Sleep 20, Walk to Beach, Free Heated Pool, Elev

Enjoy a Carefree Casual Getaway experience in this Beautifully appointed Hilton Head Island home away from home! Mid Island where you can walk/bike and take the trolly to the best beaches, restaurants and shopping on the island. Sleeps 20 - Spacious Beach House has 6 Comfortable bedrooms w/ TV's. Master bedroom has a romantic electric fireplace! FREE Heated Saltwater Pool with propane grill and dining/ comfortable seating. Fully stocked kitchen. Linens/towels/soap and shampoo all provided!

Resort-Style Pool, Cute House 88 Steps to Sand

Experience the best of island life in a resort-style setting. Recently renovated, this classic home offers comfortable living by a MAGNIFICENT beach for a memorable family-friends getaway. 1st floor features a screened in porch; open living-dining area; a well-stocked kitchen; three bedrooms (3rd bedroom with separate hallway) and two bathrooms. The new private pool space is where you can expect additional relaxation around pool, cabana with dining area, KitchenAid grill and outdoor seating.

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Offered by owner /manager. Master bath w/ walk in shower, spacious bright open concept LR, DR, kitchen, w/ private cozy courtyard. Designer inspired coastal chic for the beachy atmosphere. Sit and relax in the courtyard, lounge in the sun while having an afternoon drink and BBQ. Watch golfers at the driving range or Trent golf course just a short walk from the villa. Go for a swim in 1 of 5 community pools. Under 10 minute walk to Palmetto Dunes beach or call seasonal dune buggy for a ride.

Old Town Bluffton Home + Golf Cart No Cleaning Fee

This is Bluffton Living at its finest! This luxurious southern coastal home is located in the heart of Old Town Bluffton just a couple blocks from the Promenade & includes a new Golf Cart at no additional charge. Master is on the main floor. Walking distance to wonderful local hot spots including the coffee shops, wine bar, high end/casual restaurants, and charming boutiques. Our home has it all w/ a full kitchen w/ stainless steel appliances, Traeger grill, dishwasher, washer/dryer, & More!

HHI Escape - Beach Access, Golf Course, Pickleball

Escape to our cozy 2BR/2.5BA condo in Shipyard Plantation, the heart of Hilton Head's south end. Enjoy golf course views, a spacious living area perfect for family gatherings, and a fully equipped kitchen. Relax on the patio, stroll through the picturesque lagoon, or challenge friends to tennis or pickleball. Just minutes from pristine beach access and vibrant Coligny Plaza, our home offers easy access to island adventures. Create unforgettable memories with your family on Hilton Head Island!

Lovely 3BR in Palmetto Dunes w/ new pool & spa

Lovely 3 BR home on #2 tee of the Fazio golf course in Palmetto Dunes Resort. Near tennis/pickleball center, general store, & restaurants. Newer pool and spa. Quartz countertops. Two King BRs, 3rd BR with 2 Queens. Flat screen TVs, cable, ROKU in all BRs. Doorbell cam at front door porch with recording capability for host/guest safety. Beach access @ Omni resort and the Dunes House is a 5-10 min ride by bike and a 15 min walk. Beach towels/umbrellas/chairs not provided. Pool/spa not heated.

Enjoy time with Family and Friends

Home sleeps up to 22 guests (14 Beds) depending on sleeping arrangements.. We are located in a gated community a short walk to the beach on pathways and sidewalk. This home offers a heated screened pool keeping pesky bugs away and elevator. The main floor is open concept perfect for large families or groups to enjoy and socialize. Rear yard has BBQ, and firepit and is fully fenced. 6 Person Golf Cart available for discounted rental rate. Dill Dinkers indoor pickleball close by.

Walk to beach - 2BD/2BA retreat

Relaxing getaway for family and friends. Brigantine Quarters, located in Shipyard Plantation is one of the most picturesque properties on Hilton Head. With golf, shopping, dining, biking, and the beautiful beach nearby, BQ is your ideal vacation resort destination. 7 min walk to beach Pickleball/Tennis courts Grilling stations 2 outdoor pools 24 hr security guard Call Palmetto Bikes to reserve bikes in advance and your bikes will be in front of your condo when you arrive.