Hilton Head, SC 5+ Bedroom Vacation Rentals

Summary:Holloman Trace 23 Flip Flop PhilosophyThe Space:This newly constructed, North Forest Beach ocean home is ready to host all of your favorite people! Located in North Forest Beach, this home features all of the luxuries you crave; a private...

True Southern Living at its best! This elegant Sea Pines home with an open floor plan, ideal indoor/outdoor living, tons of natural sunlight, and steps to the world-famed sandy beaches of Hilton Head, this home is a true gem! The sun filled living...

This roomy 4th row Palmetto Dunes home is the ideal place for a sizable family hideaway or golf trip! The beach path is directly across from the home and the multiple indoor and outdoor living spaces, this home makes for an ideal getaway for any...

This property is now under new ownership and the owners are keen to make this already handsome and roomy home lighter and brighter with a goal of blowing away all guests expectations! 4 Surf Watch Way is a striking 6-bedroom, 5.5-bathroom, pet...

Summary:High Water 9The Space:Set within the esteemed Palmetto Dunes community, High Water 9 is an broad single-level luxury home designed for comfort, space, and effortless coastal living. Featuring seven elegantly furnished bedrooms, this private...

Summary:Curlew 8The Space:Curlew 8 is a opulent second-row private home featuring ocean vistas and chic, coastal décor. This modren private home in North Forest Beach is roomy and gorgeous - it was newly modernized and everything has been brought...

Summary:Piping Plover 12The Space:Piping Plover 12 is an immaculate and impressive 2nd row home located near South Beach in beloved Sea Pines Plantation. Enter this pretty home into the open and inviting entry. You are immediately greeted with the...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This striking 5-bedroom, 5.5-bathroom oceanfront home is located in the heart of North Forest Beach, offering an memorable coastal experience with sweeping...

Welcome to the BESTNEST at 60 Lawton Road in Sea Pines! Here's the skinny - just buzz us for more details: Our advertised prices are our very best rates and calendar shows real time availability. We encourage you to book online! • Charmingly...

Located right on the Atlantic in the Sea Pines Plantation, 22 Black Skimmer Rd is frequently praised as a dreamy, family-friendly escape — the kind of place where you make lifelong memories. Guests consistently highlight its fantastic location...

2 Collier Beach, Hilton Head Island. Feel luxury living at its best in this grand oceanfront 5-bedroom, 5.5-bathroom home boasting an oceanfront pool and one of the only pet friendly homes on Singleton Beach. Each bedroom comes with its own private...

Vacation in luxury in this beautiful home! This 4500 square foot home is designed ideally for multiple families. Just a 3-5 min. walk to the beach, this home has everything you could ask for! With 7 bedrooms, 7 and 2 1/2 baths, 3 living rooms and...

13 Moonshell Rd, Hilton Head is a ideal getaway for a coastal escape. With its five bedrooms and three bathrooms, it offers ample space for guests to relax and relax. The roomy fenced backyard with a private pool and outdoor bar provides a...

Tucked away just four rows from the ocean and directly across from a beach access path, this roomy 5 bedroom, 4 bathroom home offers the ideal blend of comfort, privacy, and unbeatable location.As you enter, you’re greeted by an open floor plan...

Summary:Royal RetreatThe Space:Escape to this luxury estate boasting two separate poolside structures and generous seating areas inside and out - ideal for entertaining. The roomy and handsome property is under new ownership and has been...

2nd Row Ocean! 5 Bedrooms, 4 Full baths, 2,500sq.ft. Next to Sea Pines Ocean gate.You will definitely fall in adore with this beautiful South Forest Beach home! The property is located right outside the Sea Pines ocean gate and is second row to the...

Close to fishing, the sea, and more, this smoke-complimentary vacation home brings it all within reach. Your feet will make short work of the 5-min. walk to Adventure Cove or the 13-min. walk to Burkes Beach. This 5-bedroom, 3-bathroom rental...

Summary:Summer HouseThe Space:With a fireplace, a pool, roomy common areas, and plenty of beds to lay your head down at nighttime, this bright home is the ideal place for your next hideaway. If you’re looking for a family-friendly hideaway with...