Your Perfect Hilton Head Island Getaway Starts Here
Hilton Head Properties Realty & Rentals offers a diverse selection of Hilton Head vacation rentals to suit every type of traveler. From 1-bedroom villas for a quiet coastal escape to 7-bedroom vacation homes built for family reunions and group retreats, each property is thoughtfully furnished and ready for your stay. Guests can enjoy luxurious vacation amenities such as private pools, ocean views, and easy beach access in sought-after communities like Palmetto Dunes, Sea Pines, Forest Beach, and Folly Field.
These vacation homes and villas place you close to everything that makes Hilton Head Island special—championship golf courses, scenic bike paths, local dining, and Lowcountry charm around every corner. Each rental is backed by our experienced property management team, committed to delivering a seamless vacation experience from booking to check-out.
Spend your days relaxing by the pool, exploring the island, or enjoying the comforts of a professionally managed Hilton Head vacation home. With flexible options, top-rated amenities, and personalized service, Hilton Head Properties Realty & Rentals makes it easy to plan a stress-free Hilton Head Island vacation.
Start your search today and discover vacation rentals that bring comfort, style, and convenience together in one unforgettable island stay.
123 properties available
Spacious Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to your spacious vacation home in Hilton Head Island, situated right on the oceanfront! This villa offers a prime location just steps away from the beach, allowing you to easily access the mesmerizing ocean. Whether you're whipping up a quick
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Newly Remodeled Villa Near Harbour Town at Stoney Creek1 Bedroom | 1 Bathroom | Sleeps 6Class, comfort, and a touch of prestige await at this beautifully remodeled one-bedroom, one-and-a-half-bath townhome in the sought-after Stoney Creek neighborhood of Sea Pines. This charming loft-style retreat features soaring cathedral ceilings, oversized wind
New Property
New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
Pristine Courtside Villa in Forest Beach2 Bedrooms | 2 Bathrooms | Sleeps 7 | Private PatioEmbark on an unforgettable journey to 118 Courtside Villa, a pristine 2-bedroom, 2-bathroom haven nestled in the heart of Hilton Head's Forest Beach area. This exquisite ground-floor unit, spanning 1200 sq. ft., offers a seamless blend of comfort and
Moon River at Daufuskie – 8, 9 & 10 Daufuskie Bluff Lane 3 Coastal Cottages | 9 Bedrooms Total | Riverfront Retreat with Private Dock Located on Daufuskie Island, Moon River is a private three-home compound designed for group stays, family gatherings, and special occasions. The property includes three individual cottages—e
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
New Property
New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
Fourth Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean and Pool ViewsWelcome to your perfect vacation home in Hilton Head Island! This stunning villa offers a picturesque view of the beach and pool, ensuring you have the best of both worlds. As you enter, you'll notice the ceiling fans gently circulating
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Elegant Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to your luxurious vacation home in Hilton Head Island! Each villa in Sea Cloisters is thoughtfully decorated to provide a tasteful and elegant atmosphere.As you step into your villa, you'll be greeted by spacious, open living and dining areas
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Dog Friendly Home with Golf Course Views3 Bedrooms | 2 Bathrooms | Sleeps 5Introducing 51 Wood Duck! This beautiful one level home overlooks the 14th Club Course Fairway. With the impressive fully stocked granite kitchen with breakfast table plus breakfast bar, it is ready for the chefs creations! The large deck spans the entire ba
Magnificent Luxury Retreat on North Forest Beach7 Bedrooms | 6.5 Bathrooms | Sleeps 14 | Beach GetawayEscape to the North Forest Beach area of Hilton Head Island and experience the ultimate beach vacation in this magnificent 7 bedroom, 6.5 bath home just 50 yards from the Atlantic Ocean. This custom-built retreat boasts 4500 square feet of lux
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Golf Course Retreat in the Heart of Sea Pines3 Bedrooms | 2.5 Bathrooms | Sleeps 6 | Golf Course View | One-Level HomeWelcome to 78 Governors Road, a beautifully renovated, single-level home located on the Sea Pines Country Club golf course with views overlooking the 17th tee. Set in one of Sea Pines’ most desirable areas, this home offe
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
New Property
New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
Oceanfront Luxury Home on North Forest BeachUNDER REMODEL - August 2026 – December 2027 5 Bedrooms | 3.5 Bathrooms | 13 Sleepers | Breathtaking Ocean ViewsWelcome to 19 Dune Lane, the perfect oceanfront vacation home for those seeking the ultimate island experience.Nestled in the heart of the North Forest Beach area, our oceanfront
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Updated Oceanfront Windsor Place Villa in Palmetto Dunes2Bedrooms | 2 Bathrooms | Sleeps 7 | Ocean ViewsATTENTION: Elevator inoperable during the time period of Nov. 1, 2026 until March 20, 2027, due to the elevator being replaced (Dates Subject to Change)Welcome to the spacious 2-bedroom, 2-bathroom condo located on the fourth floor of
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Exceptional Oceanfront Penthouse Villa at Sea Cloisters3 Bedrooms | 2 Bathrooms | Sleeps 8Welcome to the luxurious vacation home of Villa 501 at Sea Cloisters in Hilton Head Island. This stunning penthouse villa offers a truly remarkable oceanfront experience with breathtaking views from every room. With its three bedrooms and two baths, this spaci
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
