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
Magnificent Luxury Retreat on North Forest Beach7 Bedrooms | 6.5 Bathrooms | Sleeps 14 | Beach GetawayEscape to the North Forest Beach area of Hilton Head Island and experience the ultimate beach vacation in this magnificent 7 bedroom, 6.5 bath home just 50 yards from the Atlantic Ocean. This custom-built retreat boasts 4500 square feet of lux
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
Oceanfront Beach Oasis in Sea Pines5 Bedrooms | 4 Bathrooms | Sleeps 14 | Ocean Views | Backyard OasisWelcome to 33 Ruddy Turnstone, an exceptional oceanfront vacation home located in the prestigious Sea Pines resort of Hilton Head Island. This stunning 5-bedroom, 4 full bath, and 2 half bath beach house offers the perfect blend of modern eleg
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
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
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 comfort
Stunning Waterfront Abbington Villa in Palmetto Dunes3 Bedrooms | 3 Bathrooms | Sleeps 8Welcome to our stunning waterfront villa in Palmetto Dunes, Hilton Head! This spacious villa is the perfect vacation home, with incredible water views and beach access. With the famous Palmetto Dunes' 11-mile river-lagoon off your back deck and the private b
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
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
The Turtle Cottage – Moon River Retreat with a private dock3-Bedroom Riverfront Cottage on Daufuskie IslandLocated at Moon River on Daufuskie Island, Turtle Cottage offers direct waterfront positioning with long views across the New River toward Savannah. This three-bedroom home delivers a front-row coastal setting designed for gues
Updated Oceanfront Windsor Place Villa in Palmetto Dunes2Bedrooms | 2 Bathrooms | Sleeps 7 | Ocean ViewsATTENTION: Elevator inoperable during the time period of Nov. 1, 2026 until March 20, 2027, due to the elevator being replaced (Dates Subject to Change)Welcome to the spacious 2-bedroom, 2-bathroom condo located on the fourth floor of
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,
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