Hilton Head, SC 5+ Bedroom Vacation Rentals

16 Singleton Shores Manor, Hilton Head Island. Savor marsh and ocean vistas from every level of this home. Step into the open and bright living area, complete with a wet bar, pool table, and access to your private pool deck. Upstairs, an refreshed...

Sound Villas 1458Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'It's hard to top this striking and enormous island condo, offering beautiful vistas of the...

One of the very best located properties in Hilton Head. November and December are great for beach activities: golf, tennis, pickleball. Savor our private heated pool and spa.Book Christmas week and week before now while still available. Both...

You're going to be happy you chose this huge home with plenty of room for your family to spread out! The kitchen is very nice with dark wood cabinets, stainless steel appliances, granite countertops and bar seating for five. Adjacent to the...

44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 15 and has a enormous 16' x 32' pool, and features an outdoor fire pit ideal for a nighttime hosting around the pool or a cool day in the fall! There is plenty of seating...

Welcome to 10 Iron Clad, a beautiful multi-level, ocean front home in the award-winning Palmetto Dunes Resort. With breath taking ocean vistas from nearly every room, your family is sure to appreciate their beach vacation. A one million dollar...

This exceptional near ocean home in the heart of Palmetto Dunes is brand new to the rental market for summer 2024! With only a 5 min. walk to the beach, private pool, private dock, and a fantastic layout for families, this is sure to be a new...

Dune Lane 105Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'If you’ve been planning a group hideaway to Hilton Head but haven’t yet found the ideal...

This new, 5 bedroom, 5 ½ bath, home is a ideal fit for extended families, or as a multi-family vacation residence. Feel absolute luxury and convenience in this elegant professionally decorated coastal beach home. As a guest at Serenity Now you...

Welcome to 12 Whelk Street, Hilton Head Island's premier vacation destination, where beachside luxury meets unmatched convenience. Just 145 feet from the pristine sands of Bradley Beach, this freshly remodeled four-story property offers gorgeous...

Welcome to your dream vacation home located in the heart of Palmetto Dunes Oceanfront Resort. This elegantly appointed 5-bedroom, 4.5-bath offers the ideal blend of coastal appeal, modern comfort, and outdoor serenity ideal for creating memorable...

Summer HouseOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'With a fireplace, a pool, cavernous common areas, and plenty of beds to lay your head down at...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This impressive 5-bedroom, 5.5-bathroom home is located in the heart of North Forest Beach. Ideally located, it features direct access to the pristine sandy...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This handsome, nine-bedroom Beachcomber home sports a private pool and spa and provides broad living spaces, as well as amazing vistas of the beach and the...

Surf ScoterOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Surf Scoter offers luxury vacation rental at its best! This striking multi-level home, located just...

This home is designed to fit your next family vacation! The kitchen comes entirely equipped to meet your family's cooking needs with stainless steel appliances and bespoke cabinetry, including two ovens and microwave. The enormous kitchen island has...

This huge six bedroom seven bathroom oceanfront home has everything you've ever wanted in a vacation! As you enter the home you're greeted by a cavernous ceiling with sizable modern chandelier. On your left is the formal dining room, which...

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 cavernous fenced backyard with a private pool and outdoor bar provides a...