Hilton Head is an iconic destination year-round, and it's a great place to enjoy the more simple aspects of life. If you're looking for a place to get away from the daily hustle and bustle, the cold weather, or the everyday stressors of living in a city, why not spend an extended vacation on Hilton Head Island? Our Hilton Head vacation rentals are the perfect home away from home for a long-term stay, offering full kitchens, spaces for work and play, in-unit laundry, high-speed internet, and more.
Winter isn't for everyone, and if you're dreading the days of snow-covered ground, Hilton Head is a great destination for snowbirds. Book Hilton Head snowbird rentals to trade snow for sand and enjoy a slow-paced winter that allows you to simply unwind without crowds. Come for a few days or stay for a few months! Hilton Head Island is perfect for retirees, families, and young professionals alike.
Plan Your Winter Escape to Hilton Head Island
Learn and Work Remotely
Learning and working remotely is common these days, and the biggest benefit to that shift is that you can be remote anywhere. If you're looking for an extended stay to learn and work virtually, Hilton Head Island is a great option. From the pristine nature preserves where kids can learn about the great outdoors to the historic sites and cultural attractions, Hilton Head offers a unique perspective to learn hands-on.
Just searching for a place to work remotely? Our Hilton Head rentals are spacious and comfortable so you can set up your space to be productive when you're working and cozy when it's time to relax. We even offer pet-friendly accommodations so you don't have to leave Fido behind. Secure a home with a private pool, an oceanfront rental so you can wake up to the sound of the crashing waves, or a place in one of our popular resort communities with tons of amenities at your fingertips.
Eat in the Comfort of Your Rental Without the Effort
Low Country Grocery Runner offers grocery delivery right to your home before you arrive so you'll be set from the moment you get there. The Low Country Grocery Runner will shop at large chains like Kroger, Publix, or Whole Foods, as well as local spots like Fresh Market.
If it's the prepping and cooking part that you'd really like to do without, you can hire Chef Lynn Michelle to cook for you and your family.
Many local grocery stores are also offering curbside pickup if you place an order online, and some restaurants that are open are offering pick-up.
Things to Do in Hilton Head in the Winter
During the winter months, Hilton Head Island has mild temperatures so you can enjoy the outdoors during the day and cuddle up by a fire at night. Bring some layers and prepare for temperatures in the low- to mid-60s throughout the afternoons. This weather is absolutely perfect for outdoor adventures. Unlike the summer when it's busy, hot, humid, and thunderstorms are common, winter weather on Hilton Head is best enjoyed outside.
Kayaking is a fun way to get out on the water without getting into the water. You can rent equipment from local providers or go on a tour to discover the flora and fauna of the low country.
If you'd rather stay on land, biking is the perfect way to explore Hilton Head and get a bit of exercise. Hilton Head Island is one of the most bike-friendly communities in the country with 60 miles of bike paths and 100 miles of protected public pathways. You can bike to the beach, through forests, along marshland, and more on Hilton Head.
Hilton Head golf courses, but the winter temperatures make the experience all the better. Hilton Head Island is home to some of the country's best courses, including courses designed by famed architects like Jack Nicklaus, Robert Trent Jones Sr., and Pete Dye. A stay at Palmetto Dunes Resort and you'll have access to three world-class courses. Whether you're looking to have a casual game or you're an experienced golfer searching for a championship course, Hilton Head is the perfect golf destination.
Hilton Head Winter & Snowbird Rentals
Any great vacation or extended stay on Hilton Head starts with finding the perfect vacation home to call basecamp. At Vacation Homes of Hilton Head, we offer a great selection of rentals that you can call home for a week or for many weeks. Our luxury rentals are the perfect place to escape the cold and snowbirds for the winter. Our homes are located in the most desirable communities on the island, such as Palmetto Dunes Resort, Singleton Beach, and Burkes Beach. Secure your stay on Hilton Head with us today, or contact our team for more information.