Hilton Head Vacation Rentals
Welcome to Hilton Head Island, where relaxation meets luxury, and unforgettable memories are waiting to be made. As your premier vacation rental company on this breathtaking island paradise, we invite you to experience the ultimate getaway in one of our exquisite properties.
Nestled amidst pristine beaches, lush greenery, and world-class amenities, our hand selected collection of vacation homes promises an unparalleled escape from the ordinary. From intimate beachfront villas to spacious oceanfront homes, each of our properties is meticulously designed to cater to your every need and desire.
Beyond the confines of your vacation home, Hilton Head Island beckons with a plethora of activities and attractions to delight every traveler. Tee off at world-renowned golf courses, embark on a thrilling dolphin cruise, or simply lounge by the pool and soak up the sun. With miles of pristine beaches, scenic nature trails, and vibrant cultural experiences awaiting you, there's never a dull moment on Hilton Head Island.
We are committed to providing unparalleled service and unforgettable experiences for our guests. From seamless booking processes to our signature Luxury Concierge services, we strive to exceed your expectations at every turn. So why wait? Book your stay with us today and discover the magic of Hilton Head Island in style. Your perfect getaway awaits.
136 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This villa has been fully remodelled in a light coastal design, creating an inviting and serene retreat. This charming space is the perfect spot for a peaceful island getaway, combining modern comfort with classic coastal elegance.
As you step inside, you\'l
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
2517 Windsor Place is a beautifully appointed three-bedroom, three-bathroom oceanfront villa that blends spacious design with effortless coastal elegance. Ideal for golf getaways, family vacations, or couples traveling together, this villa offers a thoughtful
2517 Windsor II
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Exciting updates have just been completed at this property! A brand-new 5th bedroom is now finished and fully furnished with a queen-size bed and an ensuite jack-and-jill style bathroom. Updated photos have been completed as of January 2026.
Elegance is unde
51 Haul Away | Haul Away Haven
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This waterfront villa in Sea Pines offers a blend of coastal charm and relaxed sophistication, with sweeping views of the Calibogue Sound from nearly every angle. Designed to host family and friends, the stunning villa features three bedrooms, two and a half
1922 South Beach Club
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Now Complete, Stunning Outdoor Upgrades!
The beautiful new saltwater heated plunge pool and spacious back deck are now finished and ready for its first guests to enjoy. Updated professional photos of the new outdoor space are on the way so you can soon see th
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This oceanfront home sits in the prestigious Palmetto Dunes Resort and offers panoramic ocean views from every angle.
The great room, kitchen, and dining area make up the great room of the home; the extremely open floor plan allows for an easy flow and plent
10 Ketch
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
There is no need to look any further than oceanfront Beachside Bliss for your next family reunion or friends\' getaway, as this one-of-a-kind, 8,000-square-foot luxury home will spoil everyone lucky enough to come along! As soon as the sun comes up, your days
43 South Beach Lagoon
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This 2 bedroom, 2-bath Beachside Tennis villa has panoramic views of Calibogue Sound. Located in the South Beach area of Sea Pines on the first floor of a five-story building, just steps to the pool and beach,
When entering the villa, you will find the mast
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Please Note: Exterior improvement work will be taking place at Lighthouse Road Villas beginning the week of 4/20/2026. Work will include tree removal, driveway resurfacing, new sidewalk installation, electrical updates, and landscaping. Tree removal will begi
3 Lighthouse Road Villa
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunning, brand-new property was just completed in June 2025 and is ready to welcome its very first guests!
The heart of the home lies upstairs, where the main living room impresses with vaulted ceilings and a wall of windows that flood the space with n
10 Cassina Lane
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This villa has plenty of space to move around. Walk into the first floor, where you have the kitchen, dining room, and living room leading out to a small patio equipped with a new gas grill. The living room has a small desk space, perfect for any last-minute
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This property will be undergoing construction and unavailable for rental during 2026. If you have any questions, please reach out to us at or call
This beautifully upgraded vacation home combines sophisticated design, high-end finishes, and abundant natur
Tell us what you're looking for and someone will contact you with available options.