Winter on Hilton Head 2027 -Stay Longer and Save
Special Offer Ends: Sunday, November 01, 2026
Valid for Stays Between: Friday, January 01, 2027 and Sunday, February 28, 2027
Promo Code: HHIWinter27
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Trade the winter weather for a little more time on Hilton Head Island!
Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.
Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.
*To qualify, your reservation must be created on or after Tuesday, September 08, 2026. This offer does not apply to reservations made prior to this promotion.
*Offer expires 11/01/2026 and you must book your vacation between 01/01/2027 and 02/28/2027.
*Offer expires 11/01/2026 and you must book your vacation between 01/01/2027 and 02/28/2027.
379 properties available
Located in the desirable Shipyard Plantation, 102 Beachwalk offers the perfect combination of comfort, style, and location. Just a short 5-minute walk to Hilton Head\'s beautiful beaches, this charming 1-bedroom, 2-bath villa is the ideal choice for a relaxing island escape.
This villa features an open, airy layout with a bright and inviting livin
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Trade the winter weather for a little more time on Hilton Head Island!
Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.
Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.
Within earshot of the rolling surf, this 1-bed, 2-bath is a lovely villa across from the Sonesta Resort. This 2nd-floor villa is a hop, skip, and jump to the beach! Shipyard\'s location is optimum for filling your time with all the best things Hilton Head Island offers nearby.
Town of HHI STR Permit #45896
HIGHLIGHTS
- Golf course Community
- L
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Trade the winter weather for a little more time on Hilton Head Island!
Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.
Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.
This charming oceanfront 1-bedroom villa offers the perfect retreat for couples or small family getaways. Recently renovated and upgraded, this villa combines modern comforts with coastal charm. The fully updated kitchen provides all the essentials for preparing delicious meals, while the bathroom features a sleek walk-in shower, offering a spa-lik
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Trade the winter weather for a little more time on Hilton Head Island!
Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.
Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.
Enjoy a fabulous vacation in this luxuriously appointed Barrington Villa. This 1-bedroom, 1.5-bath offers phenomenal ocean views and is the perfect spot to enjoy coffee or a cocktail. Enjoy a large community heated* pool, spa, and a beachside pavilion surrounded by landscaped grounds with meandering lagoons. A boardwalk leads from the pool deck to
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Trade the winter weather for a little more time on Hilton Head Island!
Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.
Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.
**Beachfront Bliss Awaits at This Charming 1-Bedroom Villa**
Park the car, kick back, and forget about life for a while! This fully renovated beautiful 1-bedroom, 1-bath oceanfront villa offers the best location on Hilton Head Island—just steps from the beach and the vibrant Coligny Plaza. Whether you\'re seeking a relaxing getaway or an adventure
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Trade the winter weather for a little more time on Hilton Head Island!
Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.
Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.
**Maintenance Project**
-The baby pool in front of Building 3 is closed until further notice. All other onsite amenities are open.
Escape to a stunning, newly updated 1-bedroom, 2-bath villa at the renowned SeaCrest Oceanfront Resort, located in the heart of Hilton Head Island\'s Coligny Beach area. Situated on the third floor of building two,
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Trade the winter weather for a little more time on Hilton Head Island!
Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.
Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.
**Maintenance Project**
-The baby pool in front of Building 3 is closed until further notice. All other onsite amenities are open.
**Luxurious 1-Bedroom, 1.5-Bath Villa at SeaCrest Resort – North Forest Beach, Hilton Head Island**
Escape to the ultimate beachfront retreat in this stunning 1-bedroom, 1.5-bath villa located at SeaCrest Resort, ju
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Trade the winter weather for a little more time on Hilton Head Island!
Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.
Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.
One of the finest oceanfront accommodations. It is located in the heart of Palmetto Dunes Resort. This 3rd-floor 1-bedroom, 2-bath oceanfront villa offers some of the best views of the Atlantic Ocean. Windsor Place offers two large oceanfront pools and a hot tub as well as a large sundeck, poolside restrooms, showers, and a covered pavilion with a
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Trade the winter weather for a little more time on Hilton Head Island!
Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.
Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.
**Maintenance Project**
-The baby pool in front of Building 3 is closed until further notice. All other onsite amenities are open.
**1-Bedroom, 1.5-Bath Oceanfront Villa at SeaCrest Resort – Hilton Head Island**
Escape to this beautiful 1-bedroom, 1.5-bath villa at the SeaCrest Oceanfront Resort, perfectly situated on the fourth floor of build
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Trade the winter weather for a little more time on Hilton Head Island!
Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.
Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.
**Maintenance Project**
-The baby pool in front of Building 3 is closed until further notice. All other onsite amenities are open.
**Charming 1-Bedroom, 1.5-Bath Oceanfront Villa at Sea Crest Resort**
Discover the perfect beach retreat at this delightful 1-bedroom, 1.5-bath villa located on the fourth floor of building two at the prestigious Se
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Trade the winter weather for a little more time on Hilton Head Island!
Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.
Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.
Tucked within the prestigious oceanfront Windsor Place complex in Palmetto Dunes, 305 Windsor Place is a beautifully 1-bedroom, 2-bath villa that\'s perfect for a romantic escape or a peaceful solo retreat. Step onto your private balcony and take in serene views of lush landscaping and peeks of the Atlantic just beyond. Inside, you\'ll find an open
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Trade the winter weather for a little more time on Hilton Head Island!
Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.
Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.
Welcome to 306 Barrington Arms, a stunning new vacation rental in the prestigious Palmetto Dunes Resort on Hilton Head Island. This beautifully updated 1-bedroom, 1-and-a-half-bathroom oceanfront villa offers breathtaking views, upscale amenities, and a prime location—perfect for your next island getaway. Here you will enjoy a spacious open-concept
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Trade the winter weather for a little more time on Hilton Head Island!
Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.
Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.
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