Come to Hilton Head for the Holiday Season
Santa's been spotted at the beach
This holiday season, unwrap the gift of togetherness on the shores of Hilton Head Island. Create unforgettable memories with loved ones surrounded by sun, sand, and southern charm.
Your home away from home awaits in our cozy vacation rentals, perfect for large family gatherings.
We are now offering a 3-night minimum over the holidays
We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown
146 properties available
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.
1206 Sea Crest is a spacious 2nd-floor corner villa in the Sea Crest complex where you can enjoy direct oceanfront views.
As you enter the front door into a small foyer, you will notice the very nice plank-style flooring. To the left is a guest bedroom with
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This expansive property features five bedrooms and two separate entrances, providing ample space and privacy for larger groups. This property boasts multiple living areas, ensuring plenty of room for everyone to spread out and relax.
This amazing villa featu
1013 Seacrest
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This completely renovated Palmetto Dunes villa is sure to make you feel right at home! Welcome to 89 The Moorings, featuring 2 bedrooms and 3 bathrooms with enough room to host up to 8 guests very comfortably. Guests can enjoy the feel of brand new flooring,
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.
This beautifully remodeled 3-bedroom home is very stylish, with a coastal cottage vibe throughout. The property features an open living, dining, and kitchen area that is fully equipped with top-of-the-line furnishings to provide all you need for a relaxing su
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This renovated 3-bedroom, 3-bath townhome features quartz countertops, soft-close cabinets, glass tile backsplash, LVP flooring, smooth ceilings, stunning tile showers, all new lighting, and new stainless steel appliances in the fully stocked gourmet kitchen.
283 Turnberry Villas
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunning rental home offers a picturesque and convenient location, perfect for creating unforgettable vacation memories. This two-story retreat is designed for groups, with a private pool, a huge outdoor dining table, and five bedrooms with multiple bunk
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This charming Sea Pines home is 4th row from the beach and features 5 bedrooms along with 5 bathrooms and 2 half bathrooms to host 14 guests very comfortably.
The first floor features a very open floor plan that offers easy access between the multiple living
2 Royal Tern
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Located in Palmetto Dunes and only a few minutes walk to the beach, this four bedroom home has all you need for the perfect stay on the island. 3 Cartgate offers four bedrooms and four and a half bathrooms, large spacious rooms, an open kitchen and private po
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Lots of natural light shines throughout this 2-bedroom, 2-bathroom villa, just steps away from the Salty Dog.
You’ll love the recently renovated kitchen, which is located just off the foyer. All overlooking the open-concept living and dining room and out to
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This amazing island getaway is nestled among the pines beside a lagoon on 1.9 acres in the heart of Sea Pines.
This beach home offers beautiful high-end finishes in the huge eat-in kitchen and throughout, including the spacious dining room, living room, and
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