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A Guide to Vacation Homes on Hilton Head Island

By Hilton Head Insider

Teeing off on a championship golf course. Strolling along miles of white-sand beach. Perfecting your serve on the tennis court. Exploring on two wheels. There are as many ways to enjoy a visit to America’s Favorite Island® as there are unique, exciting, and memorable places to stay while you’re here with us. In fact, the Lowcountry boasts a truly incredible selection of vacation rental options, from cozy condos and charming townhouses to sprawling oceanfront homes overlooking the beach.

Read on to explore some of our favorite vacation rental options on Hilton Head Island, from family vacations to romantic rendezvous — and everything in between.

A Getaway With the Gang

From schedules to spouses, childcare to careers, the demands of everyday life can sometimes mean that time with friends falls by the wayside. So if you’re fortunate enough to find time for a Lowcountry getaway with your favorite people, you’re going to want to make the most of every minute together. And what better way to do just that than by booking a vacation home with room for the whole gang?

Gather your closest pals together for the ultimate catch-up at 52 Ocean Breeze. Offered through Island Time Hilton Head, this charming, two-story condo is located in the heart of the action, just a short stroll from Coligny Plaza and Celebration Park. An inviting living space furnished with a plush sectional sofa leads out to a beautiful open-air balcony, perfect for spending quality time together. And with three generously sized bedrooms (each with its own private bathroom), your whole group can enjoy ample space to unwind at the end of each fun-filled day.

For larger groups looking to take advantage of the incredible amenities Palmetto Dunes Oceanfront Resort has to offer, the five-bedroom oceanfront vacation home at 17 Brigantine is just the thing. Break bread together in the spacious, airy dining room, or soak up the sun on the deck of your private pool while savoring cool sea breezes and drinking in spectacular views of the Atlantic Ocean. Plus, as guests of a resort-managed vacation rental, your group can enjoy complimentary court time at Palmetto Dunes’ Tennis & Pickleball Center, special rates, and exclusive discounts on tee times, water sports, bike rentals, and more.

An Extended Workcation

Over the past few years, many people have elected to eschew the office in favor of the unmatched flexibility of a work-from-home lifestyle. But if you’ve ditched your hectic morning commute only to find yourself dogged by Zoom fatigue, it may be a sign that it’s time to shake things up with an extended “workcation” right here on Hilton Head Island.

Experience the Lowcountry like a local when you book a monthly stay at one of the incredible vacation homes, villas, or condos available through Beach Properties of Hilton Head. Perfectly appointed with luxurious furnishings, charming coastal décor, and a host of thoughtful touches, their curated selection of comfortable rentals offer the enticing change of scenery you’ve been yearning for.

Digital nomads will delight in an extended stay at 6 Cottage Court. Located within the Palmetto Dunes resort community, this four-bedroom, three-bathroom hideaway offers an abundance of plush armchairs, comfortable work desks, and secluded spaces perfect for taking your next Zoom call — in between dips in the private courtyard pool, that is. Enjoy all the comforts and conveniences of home with the fully equipped kitchen, in-unit laundry, and wireless internet. Plus, the dedicated games room equipped with a ping pong table offers plenty of opportunities to mix business with pleasure during your stay.

A Romantic Retreat

With bountiful dining options, year-round sunshine, and a seemingly endless expanse of beachfront to stroll, Hilton Head Island is the postcard-perfect setting for an intimate couple’s escape. And while a hotel room may feel like the classic choice for a getaway for two, you won’t want to sleep on the benefits of choosing a condo or villa for your next romantic retreat.

Whisk that special someone away to your own personal love nest when you book a beachside condo amid the coastal splendor of Sea Pines Resort. Spacious living and dining areas, an open-air balcony, and sweeping views of Calibogue Sound set the scene for an unforgettable experience, while practical touches like the fully equipped kitchen afford you the opportunity to spoil your better half with a thoughtful home-cooked dinner or surprise breakfast in bed.

Sea Pines also lets you enjoy the best of both worlds, combining the unmatched privacy and seclusion of a vacation rental with the convenience and unparalleled service of a resort stay. Take advantage of all this expansive resort community has to offer, including two complimentary hours of tennis for each day of your stay, along with preferred rates at championship golf courses like Harbour Town Golf Links and Heron Point by Pete Dye. As the old adage goes — the couple that plays together, stays together.

A Family Affair

It’s no secret that planning a family vacation can be a juggling act. From coordinating schedules and childcare to planning meals and activities that the whole crew will enjoy, pulling off that seemingly effortless getaway can turn out to be quite a bit of effort — especially when young kids are involved. Thankfully, Hilton Head Island boasts a wide array of vacation homes and villas designed to take the hassle out of family travel.

Families come in all shapes and sizes — and thankfully, so do our vacation rentals. Book a bright and airy three-bedroom townhouse in sought-after South Forest Beach through Island Getaway Rentals. Located a short stroll from the waterfront and the shops and restaurants of Coligny Plaza, this ocean-oriented property boasts shiplap walls, hardwood floors, and abundant natural light to bring the outdoors in. A generously sized primary suite creates a restful retreat for grown-ups, complete with a luxurious king-sized bed and private en-suite bathroom.

Looking for something to accommodate a larger brood or a multi-generational family vacation? Find your Lowcountry home-away-from-home at Island Getaway Rentals’ spectacular 20 Sea Oak Lane. This extraordinary oceanfront home contains nine bedrooms and ten bathrooms, and can comfortably accommodate a whopping 24 guests. A stunning chef’s kitchen with gas range and oversized harvest dining table are perfect for sharing family meals. And the private swimming pool, games room, and 65” outdoor cabana TV ensure endless fun and amusement, both for kids and kids-at-heart.

Excited about a family adventure but hesitant to leave Fido at home? Browse Hilton Head Island’s wide array of pet-friendly accommodations and vacation homes. Just be sure to stay mindful of seasonal restrictions and leashing requirements that help keep our island a welcoming place for all creatures, great and small.

A Once-in-a-Lifetime Experience 

From long-overdue reunions and milestone birthdays to anniversaries and wedding celebrations, there are certain special moments in life that call for a setting to match. A setting with room enough to comfortably gather together your nearest and dearest; one that not only showcases the natural beauty of our Lowcountry surroundings, but also reflects the significance of this once-in-a-lifetime moment. A setting like 47 South Beach Lagoon. 

Available through Vacation Company, this magnificent six-bedroom, seven-and-a-half-bathroom oceanfront home exudes a stately seaside elegance. Nestled along the beachfront of Sea Pines Resort’s famed Gold Coast, this luxurious oceanfront manor was designed as a place to bring people together, with a grand entryway, expansive main-floor gathering spaces, and covered open-air patio overlooking a private pool. Raise a glass to the ones you love most in the spacious gourmet kitchen, then take advantage of the property’s direct beach access to immortalize the moment with a group snapshot you’re sure to treasure for years to come. 

Your Home-Away-From-Home Awaits

Whether you’re planning a romantic retreat with the one you love, a fun-filled getaway with the girls, or an epic adventure with your entire extended family in tow, you’ll find the perfect home-away-from-home among Hilton Head Island’s incredible array of vacation rentals. Start exploring our selection of villas, condos, and breathtaking oceanfront homes, and find all the inspiration you need to plan a Lowcountry getaway you’ll be reminiscing about for years to come.

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