Hilton Head Vacation Rentals
Our curated Collection of Hilton Head vacation rentals includes carefully selected homes and villas that are among the finest properties on the island. We offer luxury rentals in Hilton Head Island's most popular locations including Sea Pines, Palmetto Dunes, North Forest Beach, South Forest Beach, and Shelter Cove. Choose from an impressive selection of oceanfront rentals, private homes, and pet friendly rentals. We offer rentals with private pools as well as properties with access to heated pools in addition to many other sought-after amenities including keyless entry, wifi internet, updated furnishings, expansive porches, fireplaces, garage access, and more. Our vacation rentals are handpicked to help create a memorable experience during your Hilton Head vacation.
138 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
2 bedroom, 3 bathroom Moorings villa close to the beach (650 feet from beach access; less than a two-minute walk) and the pool (located right outside the villa) in the sought-after Palmetto Dunes Oceanfront Resort on Hilton Head Island This Palmetto Dunes vil
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This property now offers an exciting new amenity with a free pickleball and tennis pass in Palmetto Dunes, which includes two free hours of court time every day of your stay!
Find tranquility in this cozy two-bedroom, two-and-a-half-bath Palmetto Dunes villa
8103 Wendover Dunes
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Enjoy the amazing ocean views from this lovely 2-bedroom, 2-bathroom renovated Windsor II villa. The dining table offers seating for 6, and the adjacent breakfast bar offers bar stool seating for 3.
Enjoy the spacious living room with a brand new sleeper sof
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
4 Junket sits 2nd row in Palmetto Dunes with Gorgeous Updates, Private Pool, Screened porch and Lowcountry luxury living
This second-row oceanfront, pet-friendly home is the epitome of Lowcountry luxury living on the beach. You are invited to this gorgeous m
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
253 Captain\'s Quarters, where amazing sunrises greet you in this contemporary one-bedroom villa. Coming this fall the kitchen will be renovated with new cabinets, counter tops and fixtures.
The villa is designed to offer a perfect blend of modern ameniti
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.
For a limited time, this property is offering complimentary pool heat for all new stays booked in October and November, making it even easier to enjoy the pool throughout your fall getaway.
32 Bradley Beach Road is a gorgeous beach house located a short walk
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Welcome to this spacious and beautifully designed beach retreat located in the highly sought after Singleton Beach community, known for its stunning custom homes and unbeatable proximity to the shoreline. With multiple living spaces, private balconies, elevat
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
You\'re going to love this Captain\'s Walk villa for one of the best panoramic ocean views on Hilton Head Island, for being centrally located within mid-island on new paved pathways, for having a golf course on the property, and for having conveniently locate
450 Captains Walk
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Brand New Construction 3rd row home in Palmetto Dunes!
130 Mooring Buoy is a beautiful 5-bedroom, 4.5-bath luxury home nestled in the beautiful Palmetto Dunes Oceanfront Resort. Just three rows from the beach, this home is meticulously designed for your perf
130 Mooring Buoy
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Can you just imagine hearing the birds chirping and the wildlife rustling in the greenery as you watch the herons wading in the lagoon? Can you hear the ping of the golfer\'s tee shot? Is the contact between the driver and the golf ball making the sweetest so
42 Stoney Creek
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
Tell us what you're looking for and someone will contact you with available options.