Luxury Vacation Rentals
Luxury means more than just high-end finishes—it’s about space, comfort, and unforgettable moments. At Hilton Head Properties Realty & Rentals, our collection of luxury vacation homes delivers the kind of elevated experience today’s travelers expect.
Whether you're planning a milestone celebration, a multi-family trip, or a well-earned escape, our luxury properties offer the privacy, convenience, and refined details that turn a great vacation into something truly special. Enjoy easy access to Hilton Head’s best beaches, golf, dining, and bike paths—while returning each day to a home that’s anything but ordinary.
34 properties available
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
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
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
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
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, 2028 (Dates Subject to Change)Welcome to 113 Sea Cloisters—an oceanfront villa where comfort, convenience, and coastal beauty come together seamlessly.Perch
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
Stunning Second-Row Family Oasis in Palmetto Dunes6 Bedrooms | 6.5 BathroomsThis stunning new 2020 beach home is perfect for families looking for a memorable vacation. With six spacious bedrooms and top-of-the-line amenities, this home is sure to exceed your expectations. Featuring three master suites, it's ideal for multi-generational getaways
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
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
Villa with Panoramic Ocean Views at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | OceanfrontATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to Sea Cloisters Unit 206, a newly renovated vacation villa with stunning panoramic views of the ocean and the beach. Th
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
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
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