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.
121 properties available
Coastal Queens Grant Villa in Palmetto Dunes3 Bedrooms | 2.5 Bathrooms | Sleeps 9 | Pet FriendlyEscape to the beautiful Hilton Head Island and experience the perfect vacation in this spacious and charming 3-bedroom villa. With big bedrooms, living areas, and a huge deck off the back, this villa provides ample space for your family or group. You wil
Oceanfront First Floor Villa at Sea Cloisters3 Bedrooms | 2 Bathrooms | Sleeps 8 | OceanfrontATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2027 (Dates Subject to Change)Welcome to 113 Sea Cloisters—an oceanfront villa where comfort, convenience, and coastal beauty come together seamlessly.Perch
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.
Stunning Evian Golf Villa in Shipyard3 Bedrooms | 3 Bathrooms | Sleeps 8 | Beautiful Golf ViewsWelcome to this beautiful Villa located in the gated Shipyard community of Hilton Head Island! Spend your next vacation at this 2 -level condo overlooking the 7th fairway of the Brigantine golf course.The well-equipped kitchen has stainless steel ap
Renovated Fazio Golf Villa in Palmetto Dunes3 Bedrooms | 2 Bathrooms | Sleeps 7 | Pet FriendlyWelcome to Fazio Villa 2. This is the perfect family vacation, golf group outing or weekend getaway.A big back deck overlooks 18th green of Fazio Golf course. Remodeled baths, huge great room with connected dining area, new appliances and flat screen
Dog Friendly Huntington Villa in Palmetto Dunes3 Bedrooms | 3 Bathrooms | Sleeps 8 | Lagoon ViewsThis lovely Huntington villa has the "feel of a home". Nature lover? Enjoy the tranquil views of the 11 mile lagoon and the wildlife on the lagoon.Beach lover-you're only a 3-5 minute walk across the quiet street to the beach! Spacious ope
Cozy Coastal Wendover Dunes Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | 1 Half Bathroom | Sleeps 6Welcome to Wendover Dunes, the newest ocean-side complex in Palmetto Dunes on Hilton Head Island! This vacation home offers a fantastic location overlooking the maritime forest and is just a quick 3-minute walk to the beautiful beaches.Situated o
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 Fazio Villa in Palmetto Dunes2 Bedrooms | 2.5 Bathrooms | Sleeps 6 | Scenic Lagoon ViewsEscape to the beautiful Palmetto Dunes Resort and stay in this stunning 2BR/2 BA vacation home. With a walking score that s off the charts, you ll be just minutes away from everything including the beach, golf courses, tennis courts, general store, outf
Extensive Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to our newly renovated villa, where no expense has been spared to provide you with the very best beach experience.ATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2027 (Dates Subject to Change)The villa b
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.
Newly Renovated Pet-Friendly Villa Near Harbour Town at Stoney Creek1 Bedroom | 1 Bathroom | Sleeps 4Welcome to Stoney Creek Villa 249, your ultimate relaxing and comfortable getaway located in the heart of Harbourtown on Hilton Head Island. This newly renovated one-bedroom villa boasts modern and upscale furnishings, providing a stylish and inviti
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.
Fourth Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean and Pool ViewsATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2027 (Dates Subject to Change)Welcome to your perfect vacation home in Hilton Head Island! This stunning villa offers a picturesque view of the beach a
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Refined Coastal Living in Sea Pines4 Bedrooms | 4 Bathrooms | Sleeps 12 | Backyard Oasis with Private PoolWelcome to a truly exceptional vacation home in Sea Pines—a rare blend of timeless elegance and modern comfort, now part of the Hilton Head Properties R & R rental collection. This single-level residence has been exquisitely reim
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.
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.
