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
Golf Course Retreat in the Heart of Sea Pines3 Bedrooms | 2.5 Bathrooms | Sleeps 6 | Golf Course View | One-Level HomeWelcome to 78 Governors Road, a beautifully renovated, single-level home located on the Sea Pines Country Club golf course with views overlooking the 17th tee. Set in one of Sea Pines’ most desirable areas, this home offe
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,
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
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
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
Spacious Dog Friendly Home Located in Sea Pines4 Bedrooms | 3.5 Bathrooms | Sleeps 10 | Private Pool & SpaLooking for a prime location for your next vacation? Look no further than 16 Duck Hawk, located in the heart of Sea Pines on Hilton Head Island.Upon entering the home, you'll be greeted with an expansive living room that transitio
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
Upgraded Lagoon Villa by South Beach in Sea Pines3 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet FriendlyWelcome to 1587 Lagoon Villa—an upgraded 3-bedroom, single-level retreat in the heart of Sea Pines, just a short stroll to the beach, Salty Dog Marina, and pickleball courts. Recently remodeled from top to bottom with high-end finishes, this vil
Oceanfront Penthouse Villa with Loft at Sea Cloisters3 Bedrooms | 3 Bathrooms | Sleeps 8 | Ocean ViewsWelcome to our stunning two-story villa located in the beautiful Hilton Head Island. This spacious vacation home features a unique lofted sleeping space, adding an extra touch of charm and versatility to your stay.As you enter, you'll find two
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
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.The villa boasts a range of upgrades, including new granite countertops, crown moldings, baseboards, and fresh paint on walls and ceilin
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