Hilton Head, SC 5+ Bedroom Vacation Rentals

You'll appreciate this six bedroom oceanfront home located in esteemed Palmetto Dunes Oceanfront Resort. Boasting multiple huge windows facing the oceanfront, this home provides oceanfront vistas from nearly every room! As you enter, you are first...

Vacation in luxury in this handsome 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...

Black SkimmerOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This property in the Sea Pines development sits among the natural beauty of Hilton Head Island's...

9 Sandy Beach Trail, Hilton Head Island. Welcome to your bespoke-constructed vacation home! This gorgeous property features an open-concept layout with the kitchen, living, and dining areas facing the pool, creating a seamless indoor-outdoor...

2 Collier Beach, Hilton Head Island. Feel luxury living at its best in this lavish 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...

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 enormous modern chandelier. On your left is the formal dining room, which...

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 exceptional...

This fourth floor penthouse in Captain's Walk is the ideal setting for your next vacation. Upon entering the unit, guests will savor expansive vistas of the Atlantic. The living room has two enormous couches, game table, and TV. The dining room has...

Royal RetreatOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to this luxury estate boasting two separate poolside structures and generous seating areas...

You can practically feel the sand between your toes! This Palmetto Dunes island beauty is at the end of the beach path, so you’re just a few flip-flops or barefoot steps to the ocean and fun in the sun. The first-floor living area has a handsome...

19 Sand Dollar, Hilton Head Island. Welcome to this impressive second-row ocean home blending traditional coastal Carolina styling with high-end details for a memorable beach vacation! Located directly across from a semi private beach, appreciate...

This cavernous 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...

Located at the end of the street with direct beach path access from the pool, just 2 mins. from the impressive beaches of Palmetto Dunes, this home offers a great space for your next hideaway! Savor countless sunny days by the pool and calming...

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

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 pretty professionally decorated coastal beach home. As a guest at Serenity Now you are...

4 Cockle Ct. is a Sensational Coastal Chic Home just a 5 min. walk to the beach!Upon entering this open concept home you will immediately notice the striking architectural details of the archways and the high vaulted ceilings. When walking through...

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...

16 Singleton Shores Manor, Hilton Head Island. Appreciate 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...