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
Tastefully Decorated Fourth Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to your tastefully decorated vacation home in Hilton Head Island. This two-bedroom, two-bathroom villa is the perfect destination for your beach retreat. With its well-equipped kitchen, spacious living and dining areas, and st
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Pet-Friendly Queens Grant Villa in Palmetto Dunes3 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet FriendlyEscape to Hilton Head Island and experience the perfect family vacation or weekend getaway in this true three bedroom vacation home! With spacious living areas, big bedrooms, and a huge patio off the back of the villa, you'll love the space and lo
Light, Bright, and Beautiful Pet Friendly Stones Throw Villa2 Bedrooms | 1 Bathrooms | 1 Half Bathroom | Sleeps 7Welcome to this light, bright, and beautiful two-bedroom vacation home in Hilton Head Island, just a Stones Throw to the beach! The location of this home is truly incredible, offering you the opportunity to enjoy one of the most stunning
Stunning Golf-View Oasis in Palmetto Dunes4 Bedrooms | 4 Bathrooms | Sleeps 12 | Family Fun Game RoomExperience the ultimate beach vacation at this 4-bedroom getaway with an open layout and stunning golf course views.Just a few minutes bike or walk via bike pathways to the beautiful beaches in Palmetto Dunes. Recently upgraded with gorgeous fu
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.
Charming Pet-Friendly Villa at The Cottages2 Bedrooms | 2 Bathrooms | 1 Half Bathroom | Pet FriendlyWelcome to 35 The Cottages, an idyllic vacation townhome is located in a beach community with beach club and surrounded by 50 miles of scenic bicycle paths in Hilton Head Island. Whether you're planning a family vacation, a golf group outing, or
Charming Lagoon-View Retreat in Sea Pines3 Bedrooms | 2 Bathrooms | Sleeps 6 | Dog FriendlyWelcome to your own private oasis in Sea Pines, Hilton Head Island. This charming 3-bedroom vacation home is nestled in a serene wooded setting, just inside the Sea Pines Ocean Gate. Offering a perfect blend of privacy and convenience, this home provides an i
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.
Cozy Cutter Court Villa in Sea Pines2 Bedrooms | 2 Bathrooms | Sleeps 5 | Serene RetreatWelcome to 911 Cutter Court, a second-floor villa that puts you right in the heart of Harbour Town. Overlooking the Harbour Town Golf Links Clubhouse, this two-bedroom, two-bathroom retreat offers a front-row seat to one of Hilton Head’s most iconic settin
HOT118
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
Top Floor Oceanfront Penthouse with Loft at Sea Cloisters3 Bedrooms | 3 Bathrooms | Sleeps 10 | Panoramic Ocean ViewsWelcome to Sea Cloisters 509, a magnificent oceanfront penthouse villa located on the top floor (5th floor) of the building. This three-bedroom, three-bathroom villa offers unparalleled ocean views from the vaulted living room,
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.
Elegant Beachside Getaway Villa in Forest Beach2 Bedrooms | 2.5 Bathrooms | Sleeps 6 | Stunning ViewsWelcome to this beautiful Beachside Getaway, located in the perfect spot to enjoy all that Hilton Head Island has to offer! With all remodeled bathrooms, solid surface flooring, granite countertops throughout, smooth ceilings, and beautiful fur
Luxurious Willow Oak Home in Sea Pines4 Bedrooms | 4.5 Bathrooms | Sleeps 12 | Private Pool & SpaWelcome to your luxurious vacation retreat nestled in prestigious Sea Pines. This exquisite vacation home offers the perfect blend of elegance, comfort, and convenience for your getaway. As you enter the home, you'll be greeted by an inviti
Oceanfront Paradise Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsEscape to your own oceanfront paradise in this stunning vacation home located in Hilton Head Island. With its breathtaking views and convenient amenities, this two-bedroom, two-bathroom villa is the perfect destination for your beach getaway.As you enter the
HOT251
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
