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.
118 properties available
Pet-Friendly Beach Villa in Stones Throw2 Bedrooms | 1 Bathroom | Sleeps 7 | Pet FriendlyWelcome to this beautiful beach-oriented villa in Hilton Head Island! Recently renovated to exceptional standards, this villa is sure to capture your heart. This 2-bedroom, 1-bath villa is the perfect vacation retreat, ready to provide you with an unforgettable
Beautiful Pet Friendly Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet FriendlyWelcome to this beautifully remodeled vacation home in Hilton Head Island! This newly remodeled villa awaits you in the esteemed St. Andrews Common community within the world-famous Palmetto Dunes resort. This second-floor villa is a true 2 bedroom-2 ful
Pet Friendly Tennismaster Villa Perfect For a Getaway2 Bedrooms | 2 Bathrooms | 1 Half Bathroom | Sleeps 6Discover the perfect blend of coastal elegance, resort-style amenities, and low-country charm. Located in the highly sought-after Shipyard Plantation on Hilton Head Island, this newly upgraded, two-story Tennismaster Villa offers everything you
Elegant Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to your luxurious vacation home in Hilton Head Island! Each villa in Sea Cloisters is thoughtfully decorated to provide a
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Coastal-Themed Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean ViewsATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to your dream vacation home in Hilton Head Island! Located in the beautiful Sea Cloisters building, this two-bedroom, tw
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Serene Huntington Villa in Palmetto Dunes4 Bedrooms | 4 Bathrooms | Sleeps 14 | Lagoon ViewsWelcome to our two-story, fully furnished Huntington villa located in the fantastic Palmetto Dunes Resort, just a short walk to the beach and pool.This villa offers 4 king bedrooms, each with an ensuite bathroom. The new mattresses and TV in each bedroom wil
Cozy Inverness Villa in Palmetto Dunes3 Bedrooms | 3 Bathrooms | Sleeps 8 | Pickleball/Tennis Play PackageLocated in Inverness at Palmetto Dunes, 902 Inverness offers a relaxed Hilton Head Island stay with convenient access to beaches, golf, and the resort’s extensive bike path and lagoon system. This three-bedroom villa p
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.
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
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
Spacious Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to your spacious vacation home in Hilton Head Island, situated right on the oceanfront! This villa offers a prime location jus
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Spacious Family Home on Singleton BeachNew Home Construction Next Door7 Bedrooms | 7.5 Bathrooms | Sleeps 18 | Ocean ViewsWelcome to your dream vacation home at Singleton Beach! This 7-bedroom, 7 ½-bathroom home is located in Hilton Head Island's newest and most exclusive community. As soon as you enter the home, you'll be greeted wi
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.
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.
