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
Coastal Windsor Place II Villa with Breathtaking Ocean Views2 Bedrooms | 2 Bathrooms | Sleeps 8 | OceanfrontATTENTION: 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 this professionally decorated vacation home located on the fifth fl
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
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
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 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
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
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
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
Charming Secluded Oasis in Sea Pines3 Bedrooms | 2 Bathrooms | Sleeps 8 | Dog FriendlyWelcome to our beautiful ocean-oriented vacation home, perfectly situated just inside the Sea Pines Ocean Gate on Hilton Head Island. This delightful 3-bedroom home, including a loft, offers a serene and tranquil setting surrounded by lush greenery. Immerse yourse
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
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
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
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