Luxurious Hilton Head Vacation Rentals
Elevate your next island getaway with our exclusive collection of Hilton Head luxury vacation rentals. These handpicked homes and villas offer upscale amenities like oceanfront views, private pools, designer interiors, and chef-ready kitchens. Located in prestigious communities such as Sea Pines, Palmetto Dunes, and Forest Beach, our luxury rentals are perfect for special occasions, group travel, or simply treating yourself to the best Hilton Head Island has to offer. Enjoy exceptional service from Hilton Head Properties R&R, where every detail is managed to perfection. Start planning your five-star Hilton Head Island vacation today.
34 properties available
Exquisite Third Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean ViewsWelcome to our beautiful vacation home in Hilton Head, SC! This exquisite two-bedroom, two-bathroom condominium is the ideal destination for your next family vacation. Step inside and be greeted by fresh, coastal decorations that create a relaxin
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
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
Coastal Getaway in Palmetto Dunes3 Bedrooms | 2.5 Bathrooms | Dog FriendlyWelcome to our beautifully remodeled villa, the perfect vacation home for families, golf groups, corporate retreats, or anyone looking for a peaceful getaway. This 3BR/2.5BA villa sleeps 8 guests and is located on the first floor of a two-story villa complex in Palmetto
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
Villa with Panoramic Ocean Views at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | OceanfrontWelcome to Sea Cloisters Unit 206, a newly renovated vacation villa with stunning panoramic views of the ocean and the beach. The unit has a prime location on the second floor, with breathtaking views of the wide sandy beach and the ocean, and is so clo
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
The Grouper Cottage – Moon River with a Private Dock3 Bedrooms | 3 Bathrooms | Sleeps 6 |Waterfront | Private DockRiverfront Cottage located within the Moon River compound on Daufuskie Island, Grouper Cottage offers direct waterfront views and a layout designed for relaxed, coastal living. This three-bedroom home provides a comforta
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
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
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
Stunning Lagoon-View Home in Palmetto Dunes7 Bedrooms | 6.5 Bathrooms | Sleeps 18 | Private Pool | Golf SimulatorLooking for a vacation home that offers something for everyone in the family? Look no further than 25 Starboard Tack in Palmetto Dunes.This stunning home boasts spacious living areas and multiple bedroom wings, perfect for families or mu
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