Escape to Hilton Head Island for the Perfect Holiday Getaway!
It's not too early to start planning! Escape the winter chill and bask in the warmth of Hilton Head Island this holiday season. Known for its pristine beaches, world-class golf courses, and stunning natural beauty, Hilton Head Island promises unforgettable memories and festive cheer for everyone.
We are now offering a 5-night minimum for homes and a 4-night minimum for villas over the holidays.
We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown
134 properties available
1506 Villamare, Luxury 5th Floor, Closest to the Beach, Views All Around
Nestled in the private oceanfront complex of Palmetto Dunes is a 3-bedroom, 3-bathroom home with perfect access to the beach and pool. The property features a complex pool, indoors and out! You will also have access to the complex elevator, hot tub, gym, and Palmetto Dunes Bu
Welcome to 9 Flamingo Street in the charming town of Hilton Head! This stunning rental home offers a picturesque and convenient location, perfect for creating unforgettable vacation memories. This two-story retreat is designed for groups, with a private pool, a huge outdoor dining table, and five bedrooms with multiple bunk options. Spread out betw
Welcome to 867 Ketch Court! This 2-story Sea Pines villa has been recently renovated and places you only steps away from Harbour Town and a short bike ride to the Sea Pines Beach Club!
On the first floor, find the living room, kitchen, and dining area. The living room features comfortable seating , sofa bed, as well as a large flatscreen TV and cl
Fabulous two-story second row home The balconies and decks overlook the incredible pool. Take the secret path through the canopy and reach the beach in a 1-minute walk. This 6-bedroom, 5.5-bath home with 2 living rooms sleeps 15 and promises unforgettable family vacations in a spacious and elegant setting.
The first floor has a wide open floor pla
1 Man O War
504 Barrington Arms is a lovely three-bedroom, three-bathroom direct oceanfront condo on the fifth floor. Enjoy panoramic ocean views and updated furnishings and décor throughout. The dining area is adjacent to both the living room and the well-equipped kitchen.
The primary bedroom is off the dining area to the right. It has a king bed and privat
Welcome to 1584 Lagoon, the Blue Heron Villa! This completely renovated (2024) 2 bedroom, 2 bathroom property is perfectly located within steps of South Beach Marina, a short five minute walk to South Beach, and a three minute walk to tennis, pickleball, The Salty Dog Café, restaurants, and shopping.
The property includes two reserved parking spa
Welcome to 2 Royal Tern! This charming Sea Pines home is 4th row from the beach and features 5 bedrooms along with 5 bathrooms and 2 half bathrooms to host 14 guests very comfortably.
The first floor features a very open floor plan that offers easy access between the multiple living spaces, kitchen and wet bar, and dining room. Guests can enjoy pl
2 Royal Tern
Nestled in the charming Burke\'s Beach on Hilton Head Island, this remarkable 6-bedroom, 5 1/2-bathroom home is a coastal paradise that offers a luxurious and comfortable lifestyle. As you step inside, you\'ll be greeted by a spacious and well-designed interior that seamlessly blends modern amenities with beachside elegance.
The open-concept livi
1 Sandy Beach Trail
Welcome to 4303 Island Club! This two-bedroom, two-bath ocean view condo features expansive ocean views from the patio, a variety of shared pools, and nearby beach access for the perfect island vacation.
Walk into your oasis and find the kitchen, dining room, and living room with an open layout leading to your private balcony patio. Right from the
Lots of natural light shines throughout this 2-bedroom, 2-bathroom villa, just steps away from the Salty Dog.
You’ll love the recently renovated kitchen, which is located just off the foyer. All overlooking the open-concept living and dining room and out to the Calibogue Sound.
The master bedroom consists of a king bed, a walk-in closet, and an
This beautifully updated 5-bedroom, 4-bath home with a 2-car garage, elevator, and private pool is located at Singleton By The Beach. This home is located by the beautiful Chaplin Park, which offers free tennis, pickleball, basketball courts, and walking trails!
The coastal chic décor offers modern elegance that is perfect for a relaxing beach vac
Single-level home with 3 bedrooms and a short walk to the beach! Enjoy close access to the beach in this fully renovated coastal chic ranch home with a hot tub and private outdoor shower! All-new kitchens, baths, furniture, and more ensure a comfortable and relaxing vacation. Experience true Sea Pines living that pulls the outdoor vistas in through
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