Long Stay 2025 | 2026
Stay a while in Hilton Head at one of our 10 Most Popular Properties
Hilton Head offers a perfect blend of relaxation and activity. The island's mild climate, especially in the fall and winter, is ideal for outdoor pursuits like golfing, biking, pickleball, tennis, and beachcombing. With diverse dining, shopping, and cultural attractions, there's always something to explore.
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10 properties available
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.
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.
This pet-friendly Sea Pines home has an extremely open floor plan with soaring ceilings to create a charming environment perfect for your next vacation. Three bedrooms and three bathrooms offer enough space to host up to 10 guests comfortably. Multiple living
36 Red Oak
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
1506 Villamare, Luxury 5th Floor, Closest to the Beach, Views All Around
Nestled in the private oceanfront complex of Palmetto Dunes is a 3-bedroom, 3-bathroom home with perfect access to the beach and pool. The property features a complex pool, indoors and
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Beautifully updated 3-bedroom villa in Shelter Cove. Come in, take a seat, and relax in the living room. The living room, kitchen, and dining room have an open layout. The kitchen has granite countertops, new stainless steel appliances, and smooth ceilings.
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This 2 Bedroom 2 Bathroom villa is located in Palmetto Dunes in the tranquil Queens Grant neighborhood. This open plan villa is the perfect place for a peaceful Island escape. With it\'s open plan, and coastal blues interior, you\'ll find everything you need
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This charming two-bedroom, two-story townhouse is located in the highrise building at the oceanfront Island Club, featuring a lagoon view from the private deck. Walk right out to the grounds from the deck or spend your evening cooking dinner with the family i
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.
This beautifully updated 5-bedroom, 4-bath home with a 2-car garage, elevator, and private pool is located at Singleton By The Beach. This home is located by the beautiful Chaplin Park, which offers free tennis, pickleball, basketball courts, and walking trai
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
2211 Seacrest has new LVT floors with walk-in showers, a garden tub, double vanities, and more!
This is a wonderful 2-bedroom, 2-bathroom villa located on the second floor of Building 2. Walk-in to the open-concept living space, perfect to spread out and rel
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