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
The Crab Cottage – Moon River Retreat with a private dock3-Bedroom River View Cottage on Daufuskie IslandLocated at Moon River on Daufuskie Island, Crab Cottage offers elevated water views across marsh and river landscapes toward Savannah. This three-bedroom home provides a slightly set-back position while still maintaining strong v
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 Windsor Place II Villa in Palmetto Dunes3 Bedrooms | 3 Bathrooms | Sleeps 8 | OceanfrontATTENTION: Elevator inoperable during the time period of Nov. 1, 2026 until March 20, 2027, due to the elevator being replaced (Dates Subject to Change)Located just steps from the sand in the heart of Palmetto Dunes, 2117 Windsor Place 2 offers
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Beautiful Lagoon View Villa in Palmetto Dunes3 Bedrooms | 4 Bathrooms | Sleeps 11 | Lagoon ViewsWelcome to Sweet Perfection, a beautifully furnished villa located in the heart of the sought-after Palmetto Dunes Resort. This townhome features three oversized bedrooms and four full baths, perfect for accommodating your entire crew! The villa boasts b
Your Beachside Oasis in Folly Field4 Bedrooms | 4 Bathrooms | Sleeps 14 | Private Pool & SpaWelcome to your dream getaway—a stunning, purpose-designed 4-bedroom beachside home in the heart of Hilton Head Island's beloved Folly Field neighborhood. Just steps from the pristine sands of a serene beach, this home promises a perfect b
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!
Coastal-Style Oceanfront Villa at Sea Cloisters3 Bedrooms | 2 Bathrooms | Sleeps 8 | OceanfrontWelcome to your own piece of paradise at Sea Cloisters! This three-bedroom villa has been designed with your comfort and convenience in mind. All three bedrooms are on the same level, making it easy to access and perfect for families or groups of friends.
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Cozy Stones Throw Villa Ideal for Family Getaways3 Bedrooms | 2 Bathrooms | 1 Half Bathroom | Sleeps 8Welcome to this wonderful 3-bedroom, 2.5-bathroom villa in Hilton Head Island, offering the perfect setting for an unforgettable beach vacation. Situated just a short stroll away from the Atlantic Ocean and miles of pristine beach, this villa provi
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
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Luxury Oceanfront Villa in Palmetto Dunes3 Bedrooms | 3 Bathrooms | Sleeps 8 | Luxury GetawayYou'll immediately notice the fresh, new feeling as you enter the villa, with brand new living room furniture, appliances, mattresses, and flooring in the bedrooms. We've also installed Mesh WI-FI to ensure strong WI-FI performance throughout the en
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.
Garden View Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | Sleeps 4 | Garden ViewsWelcome to 1679 St. Andrews Commons, a comfortable two-bedroom villa located within Palmetto Dunes on Hilton Head Island. Surrounded by mature landscaping and peaceful garden views, this villa offers a relaxing retreat for families, couples, and small groups lookin
New Property
New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
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.
Stunning Vacation Oasis on North Forest Beach7 Bedrooms | 5.5 Bathrooms | Sleeps 22 | Stunning BackyardLooking for a vacation home with a spectacular outdoor space? Look no further than 16 Mallard St in North Forest Beach! This stunning 7-bedroom, 5.5-bathroom home boasts the best backyard on the island, including a huge private pool and
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.
