Snowbird & Extended Stays
Looking to Stay a Little Longer?
Hilton Head is even better when you have time to settle in.
If you're planning a longer winter stay, our Vacation Planners can help you find the right property for your time on the island. Give us a call or send us an email to explore availability and options for extended stays.
Stay longer. Settle in. Make Hilton Head feel a little more like home.
123 properties available
Third Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to your dream beach getaway at 304 Sea Cloisters! Perched on the 3rd floor with sweeping views of the Atlantic, this fully remodeled 2-bedroom, 2-bath villa offers direct oceanfront bliss and modern coastal luxury—no expense spared. Step onto
Pristine Courtside Villa in Forest Beach2 Bedrooms | 2 Bathrooms | Sleeps 7 | Private PatioEmbark on an unforgettable journey to 118 Courtside Villa, a pristine 2-bedroom, 2-bathroom haven nestled in the heart of Hilton Head's Forest Beach area. This exquisite ground-floor unit, spanning 1200 sq. ft., offers a seamless blend of comfort and
Stunning Fazio Villa in Palmetto Dunes2 Bedrooms | 2.5 Bathrooms | Sleeps 6 | Scenic Lagoon ViewsEscape to the beautiful Palmetto Dunes Resort and stay in this stunning 2BR/2 BA vacation home. With a walking score that s off the charts, you ll be just minutes away from everything including the beach, golf courses, tennis courts, general store, outf
Garden View Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | Sleeps 4 | Garden ViewsWelcome to 1679 St. Andrews Commons, a comfortable two-bedroom villa located within Palmetto Dunes on Hilton Head Island. Surrounded by mature landscaping and peaceful garden views, this villa offers a relaxing retreat for families, couples, and small groups lookin
Your Beachside Oasis in Folly Field4 Bedrooms | 4 Bathrooms | Sleeps 14 | Private Pool & SpaWelcome to your dream getaway—a stunning, purpose-designed 4-bedroom beachside home in the heart of Hilton Head Island's beloved Folly Field neighborhood. Just steps from the pristine sands of a serene beach, this home promises a perfect b
Coastal Fourth Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Panoramic Ocean ViewsIndulge in the ultimate tropical getaway at this professionally decorated vacation home in Hilton Head Island. Located on the fourth floor, this condo offers a luxurious and inviting atmosphere.As you step inside, you'll be captivate
Pet-Friendly Villa at St. Andrews Commons2 Bedrooms | 2 Bathrooms | Sleeps 6Welcome to our St. Andrews Commons vacation home, located in the renowned Palmetto Dunes Resort on Hilton Head Island. This second-floor villa offers a comfortable and inviting atmosphere for your stay. As you step inside, you'll find a fully equipped kitchen with full-
Oceanfront Paradise Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsEscape to your own oceanfront paradise in this stunning vacation home located in Hilton Head Island. With its breathtaking views and convenient amenities, this two-bedroom, two-bathroom villa is the perfect destination for your beach getaway.As you enter the
Beach-Themed Third Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to your perfect beach getaway in Hilton Head Island! This tastefully decorated oceanfront villa offers stunning views of the ocean and provides a delightful ambiance. With two bedrooms and two bathrooms, this villa is the ideal vacatio
Upgraded Lagoon Villa by South Beach in Sea Pines3 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet FriendlyWelcome to 1587 Lagoon Villa—an upgraded 3-bedroom, single-level retreat in the heart of Sea Pines, just a short stroll to the beach, Salty Dog Marina, and pickleball courts. Recently remodeled from top to bottom with high-end finishes, this vil
Cozy Coastal Wendover Dunes Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | 1 Half Bathroom | Sleeps 6Welcome to Wendover Dunes, the newest ocean-side complex in Palmetto Dunes on Hilton Head Island! This vacation home offers a fantastic location overlooking the maritime forest and is just a quick 3-minute walk to the beautiful beaches.Situated o
Oceanfront Luxury Home on North Forest BeachUNDER REMODEL - August 2026 – December 2027 5 Bedrooms | 3.5 Bathrooms | 13 Sleepers | Breathtaking Ocean ViewsWelcome to 19 Dune Lane, the perfect oceanfront vacation home for those seeking the ultimate island experience.Nestled in the heart of the North Forest Beach area, our oceanfront
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