Hilton Head, SC 5+ Bedroom Vacation Rentals

This fourth floor penthouse in Captain's Walk is the ideal setting for your next vacation. Upon entering the unit, guests will appreciate expansive vistas from the living room with two enormous couches and a huge flat screen TV. The dining room off...

44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 15 and has a sizable 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...

Sea PointeOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This handsome five-bedroom home is just steps away from Singleton Beach and the shared community...

This 5 bedroom, 5.5 bath, single-family Singleton Beach home will be an island getaway 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...

Lookout 1Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please read our important pool heat information to help you have the best vacation possible!*This...

Amore Beach House Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'The Amore Beach House is a brief two-min. walk to the beach on a peaceful street in North...

This lagoon front Hilton Head Island home is located directly across the street from the beach access point and sits on one of the biggest tons in Palmetto Dunes Oceanfront Resort. The back deck is the ideal spot to appreciate the coastal breeze and...

32 Corrine Lane is a gorgeously decorated 6-bedroom, 6-bath open concept home that is really a extravagant getaway for families or sizable groups. The presence of three primary king bedroom suites, private balconies and a private pool ensure that...

Don't miss out on this Awesome Oceanfront home with many amenities the island of Hilton Head that has great all year-round weather and known for its sizable, charming beaches where early morning walks and bicycle rides is the thinks to do to start...

Stunning second row 5 Bedroom home that has been completely refreshed and has a private pool. The floor plan is unique, and offers tremendous flexibility providing both privacy and great common areas that are ideal for two families. Private & gated...

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...

Gunnery 10 Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Step into your island getaway and make the best memories with friends and family in no time here at...

Appreciate sweeping expansive vistas of multiple greens of the Robert Trent Jones Golf Course and a enormous part of the 11 mile lagoon system! See the sunrise over the iconic 10th hole of Robert Trent Jones every morning! There are amazing vistas...

*New Construction Update(Spring 2025): Updated Kitchen, Updated Master Bathrooms, Updated Half Bathroom, (Jack n Jill Bathrooms to be refreshed winter 2025), New Washer and Dryer sets*9 Singleton Beach, Hilton Head Island. This oceanfront gem is a...

18 Sand Dollar, Hilton Head Island. Your search for the ideal vacation rental ends here! With 7 bedrooms, 7 bathrooms, and an open-concept floor plan, this property is sure to impress. The upsized chef's kitchen is ideal for cooking up delicious...

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...

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...

Piping Plover 12Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Piping Plover 12 is an immaculate and striking 2nd row home located near South Beach in...