Five Bedroom Rentals
12 properties available
Breathtaking ocean views from almost every room in the house with grand architectural interiors greet you at 27 Duck Hawk - a true oceanfront retreat and one of our guests' favorite Hilton Head SC beach house rentals! This five-bedroom, five-and-a-half-bath home has many upgraded features that will make every ounce of preplanning well worth it! T
*More photos to come by June 1, 2026!Governors Lane 38, perfectly positioned just minutes from the Sea Pіnes front gate, is the epitome of luxury and comfort, designed for those seeking a memorable escape. This tri-level, custom-built home accommodates up to nine guests with five beautifully appointed bedrooms and three and half bathrooms, ensuring
Welcome to the definition of South Carolina Lowcountry living! This 5 bedroom, 3 bath Shipyard home is the perfect place for your next group getaway on Hilton Head Island! Just beyond the foyer is an open recreation room with a pool table and two plush leather chairs. The kitchen offers an island, granite countertops, a bay window, and stainless st
This 5 bedroom, 5.5 bath, single-family Singleton Beach home will be an island oasis that you won't want to leave! This well-equipped home features a private pool, designer decor, and state-of-the-art appliances, as well as double garages and a wide driveway.The first-floor pool level features a cozy sitting room decorated with a tropical motif. **
ACROSS THE STREET FROM THE ENTRANCE TO FOLLY FIELD BEACH BOARDWALK sits a charming ‘Old Hilton Head Island’ Beach House. COMPLETELY REMODELED in 2024 this 1950’s beach house was a two that now provides an UPPER LEVEL 3 BR/2 BA house complete with a large primary (king) suite and 2 bedrooms, one queen and one with bunk beds (full and single) and a s
2 Lookout in Hilton Head's Palmetto Dunes Resort area will be your family's next premier vacation destination. The owners of this home completed an extensive renovation and redecorating in the Spring of 2023. This home offers a spectacular outdoor space, unparalleled amenities and is located just a 3-5 minute walk to the beach! This spacious and b
32 Crabline Court is an exquisitely decorated 5 bedroom, 4 bathroom home located in Hilton Head’s Singleton Beach rentals area. It offers a short walk, or bike ride, to Singleton Beach as well as quick access to the beautiful Chaplin Park, shops, restaurants and Hilton Head attractions and activities.Approximately 10 steps up lead to the porch, a g
Welcome to 4 Gunnery Lane, a quintessential Sea Pines home! This beautifully outfitted five bedroom, five and half bathroom home offers the comfort and space you deserve for your next family vacation. With multiple living spaces, bedrooms spanning multiple levels and a perfectly private pool area, this home will soon become your go-to Hilton Head g
Bring your family, your pet, some friends, and still find plenty of room for rest and relaxation in this 3,100 square foot 5 bedroom, 4.5 bath raised single home. Crabline 39 is a pet-friendly vacation rental in a prime location in Singleton Beach, Hilton Head Island. This Singleton Beach home on Hilton Head Island allows you to easily enjoy the gr
112 Oceanwood, is an elevated, free-standing home in North Forest Beach and just 200 yards from the Atlantic Ocean! An oversized deck wraps halfway around the home, including a sitting area and outdoor dining area with a gas grill. Stairs from the back deck offer easy access to the Oceanwood complex pool and beach path.Ascend the exterior stairs to
Your Perfect Family Getaway!With spacious rooms, elegant furnishings, and an exceptional outdoor space, 26 Gloucester is the ideal retreat for your next family vacation.The open-concept living area offers plenty of seating, a large wall-mounted Smart TV, and sliding doors that open to an elevated deck. The deck showcases stunning views of the pool,
Welcome to 1 Cedar Waxwing, a quintessential, luxurious Hilton Head vacation home. This 5-bedroom, 5.5-bathroom, 4th row home is located on a corner lot in Sea Pines, offering guests premier accommodations with ample space and privacy. The elevated main level features an open-concept floor plan. The living area is comfortably furnished with a couch
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