Sleeps up to 6
Ideal vacation properties for couples, families & small groups!
Discover the perfect getaway with our vacation rentals on Hilton Head Island that comfortably sleep up to 6 guests. Ideal for couples, families or small groups, these rentals offer spacious living areas, fully-equipped kitchens, and cozy bedrooms. Enjoy easy access to Hilton Head's premier beaches, world-class golf courses, and vibrant local attractions. Our rental properties provide modern amenities, including high-speed Wi-Fi, flat-screen TVs, and private outdoor spaces.
Book your Hilton Head Island vacation rental today for an unforgettable stay in this beautiful coastal paradise, where comfort and convenience meet. Experience the ultimate blend of relaxation and adventure with us!
33 properties available
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!
Indulge in the tranquility of coastal living with this exquisite 3-bedroom, 3-bathr
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Enjoy endless coastline views from this corner villa on the fifth-floor face of the Windsor Court South building in Palmetto Dunes. Take in breathtaking panoramic views from the screened porch or one of the many balconies that can be found off the living room
3507 Windsor Court South
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
From the moment you walk through the front door, natural light comes flooding in from the windows. The living room is the perfect place to relax with its comfortable furnishings, large screen TV, and access to the balcony through a glass sliding door located
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Penthouse 3-bed villa overlooking the world-famous Harbour Town Yacht Basin, just steps away from Harbourtown
A great room with dual sofas facing a large flat-screen TV A set of sliders gives entrance to a whimsically tiled patio with a postcard-perfect view
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This completely renovated (2024) 2 bedroom, 2 bathroom property is perfectly located within steps of South Beach Marina, a short five minute walk to South Beach, and a three minute walk to tennis, pickleball, The Salty Dog Café, restaurants, and shopping.
T
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
4 Ocean Club offers you the perfect beachfront getaway in South Forest Beach! With direct beach access and a private, heated pool, this villa offers the best of Hilton Head Island vacationing.
Step into the inviting first floor, where you\'ll find a fully-eq
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This 3rd-floor villa is recently updated and places you just minutes outside of the world-famous Harbour Town. With 2 bedrooms and 2 bathrooms, this Sea Pines villa can sleep up to 4 people comfortably. The living room is illuminated with natural light and ha
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Take in the ocean views at this wonderful 1-bedroom villa. The open kitchen and living area are well-appointed to accommodate all your needs. The kitchen has been recently renovated. The dining table seats 2. The living room has a queen sleeper sofa. The prim
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.
2538 Gleneagle Green is a pet-friendly Harbour Town villa with stunning views of Harbour Town Golf Course and is located just a short 5-minute walk to the shops and dining at Sea Pines Center, as well as the famed Harbour Town Marina!
The open-concept floor
2538 Gleneagle Green
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
510 Mainsail is a gorgeous two-bedroom, two-and-a-half-bath, top-floor villa with breathtaking panoramic views of Shelter Cove Harbour. Designer-decorated, this property is perfect for a Hilton Head vacation and comfortably accommodates up to four people. Th
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
103 Seacrest is beautifully decorated and fully renovated for your comfort and convenience. Here, you will experience only the best. This charming property features two bedrooms, creating a cozy and inviting atmosphere for your stay. Allow me to paint a pictu
103 Seacrest
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