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
Peaceful Coastal Living Near the Beach in Sea Pines 3 Bedrooms | 2 Bathrooms | Sleeps 6 | Community Pool | Pet Friendly Tucked among the pines and just a quick walk from the beach, 66 Night Heron offers relaxed island living in one of Sea Pines’ most convenient locations. This freestanding home blends privacy with easy acc
Pet-Friendly Queens Grant Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | Sleeps 4 | Pet FriendlyWelcome to your perfect vacation destination at 597 Queens Grant, a 2-bedroom villa located in Palmetto Dunes. With its convenient location, this villa offers easy access to everything that Palmetto Dunes has to offer, including a 7-minute walk to the
Oceanfront Penthouse Villa with Loft at Sea Cloisters3 Bedrooms | 3 Bathrooms | Sleeps 8 | Ocean ViewsWelcome to our stunning two-story villa located in the beautiful Hilton Head Island. This spacious vacation home features a unique lofted sleeping space, adding an extra touch of charm and versatility to your stay.As you enter, you'll find two
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-
Charming Evian Villa in Shipyard2 Bedrooms | 2 Bathrooms | Sleeps 8 | Golf ViewsWelcome to117 Evian Villa, your perfect seaside getaway in Hilton Head Island's exclusive Shipyard community! This charming 2-bedroom, 2.5-bath villa offers a unique blend of comfort and convenience, providing an idyllic retreat for families and vacationers alike.&n
Spacious Dog Friendly Home Located in Sea Pines4 Bedrooms | 3.5 Bathrooms | Sleeps 10 | Private Pool & SpaLooking for a prime location for your next vacation? Look no further than 16 Duck Hawk, located in the heart of Sea Pines on Hilton Head Island.Upon entering the home, you'll be greeted with an expansive living room that transitio
Elegant Oceanfront Penthouse Villa at Sea Cloisters3 Bedrooms | 3 Bathrooms | Sleeps 8 | Stunning Ocean ViewsWelcome to our elegant penthouse villa located in Hilton Head Island's renowned Sea Cloisters. This tastefully decorated vacation home offers breathtaking views of both the ocean and the Sea Cloisters pool. As you step inside, you&#
Exquisite Third Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean ViewsWelcome to our beautiful vacation home in Hilton Head, SC! This exquisite two-bedroom, two-bathroom condominium is the ideal destination for your next family vacation. Step inside and be greeted by fresh, coastal decorations that create a relaxin
Tastefully Decorated Fourth Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to your tastefully decorated vacation home in Hilton Head Island. This two-bedroom, two-bathroom villa is the perfect destination for your beach retreat. With its well-equipped kitchen, spacious living and dining areas, and st
Golf Inverness Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | Sleeps 6Welcome to our newly remodeled Palmetto Dunes vacation home, a 2 bedroom, 2 bathroom villa that overlooks the beautiful fairway of the famous George Fazio Golf Course and lagoon. Step out onto the deck and take in the stunning views while relaxing on the comfortable patio furn
Family Friendly Villa in Palmetto Dunes4 Bedrooms | 3 Bathrooms | Sleeps 10Escape to your dream vacation home in Palmetto Dunes Resort, where luxury, comfort, and endless fun meet.This beautifully furnished, two-story townhouse at 975 Inverness Village Villas offers three bedrooms, three baths, and a loft that sleeps ten, making it perfect for
Stunning Lagoon-View Home in Palmetto Dunes7 Bedrooms | 6.5 Bathrooms | Sleeps 18 | Private Pool | Golf SimulatorLooking for a vacation home that offers something for everyone in the family? Look no further than 25 Starboard Tack in Palmetto Dunes.This stunning home boasts spacious living areas and multiple bedroom wings, perfect for families or mu
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