Come to Hilton Head for the Holiday Season

Santa's been spotted at the beach

This holiday season, unwrap the gift of togetherness on the shores of Hilton Head Island. Create unforgettable memories with loved ones surrounded by sun, sand, and southern charm.

Your home away from home awaits in our cozy vacation rentals, perfect for large family gatherings.

We are now offering a 3-night minimum 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


Properties Available 138 properties available
Modern comforts meet the classic styling of this traditional beach home. If you are looking for a house that has the look and feel of the beach house from your childhood memories, look no further. The home has gone through a complete renovation to restore it to its original beauty. The home offers five bedrooms and four bathrooms, just three rows
4 Quail Street
House -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 4.8 (8)
Vacation Homes In Sea Pines Close to Harbour Town and just a short bike ride to the beach, these three homes are located on a serene street in Sea Pines and only a few steps apart. Each home has a bedroom on the main level for guests unable to handle stairs, and each has a private pool. There are a total of eight king/queen bedro
Family Reunion for up to 28 Guests - 3 Units Icone Collection Icon
Bedrooms 3 - 5 bedrooms
Bathrooms 2 - 6 baths
Guests 8 - 12 guests
Rating 4.9 (26)
Please be advised that from September 2023 to April 2024, an infrastructure project will happen on Mooring Buoy. There may be limited or no access to your driveway and/or mailbox at certain times during the project. This fantastic 2nd row of the ocean is nestled in the palms of the Palmetto Dunes resort. With 6 bedrooms and 6.5 baths, this low-cou
Hot HOT 56
3 Iron Clad
House -
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 12 guests
Rating 4.7 (7)
32 Bradley Beach Road is a gorgeous beach house located a short walk to the beach, sleeping 9 guests in 3 bedrooms, 3 bathrooms, and a bonus room. This lovely home is exceptionally well maintained and has ample room to spread out in the living room, which has a sofa that converts into a queen bed. The kitchen is equipped with stainless steel applia
Hot HOT 68
32 Bradley Beach Road
House - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 5 (2)
This newly renovated 3-bedroom, 3-bath townhome features quartz countertops, soft-close cabinets, glass tile backsplash, LVP flooring, smooth ceilings, stunning tile showers, all new lighting, and new stainless steel appliances in the fully stocked gourmet kitchen. The open-concept family room features an oversized sectional couch and two plush ar
283 Turnberry Villas Fairway Collection Icon
Villa -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (7)
This 3 bedroom, 3 bathroom, two story private condo is spacious and tastefully decorated. On the first floor there is a large living area with a 60" TV and entertainment center which looks out to a large sliding glass door and the private deck. The fully equipped kitchen including a Keurig coffee maker, has plenty of counter space and cabinets, and
52 Ocean Breeze
Villa -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (3)
This gorgeous Sea Pines villa has been recently renovated and features golf and lagoon views. Walk into an open-concept kitchen, dining room, and living room. Relax on either of the comfortable couches in the living room and watch your favorite programs on the large flat-screen cable TV, or relax in the Carolina room at the rear of the villa, featu
Hot HOT 54
3 Lighthouse Road Villa Fairway Collection Icon
Villa - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
Welcome to 5 Jessamine Place, only a 10-minute walk to the best beach on Hilton Head Island! This ranch-style cottage home is newly renovated and beautifully furnished. It offers four bedrooms and four bathrooms to comfortably host up to 13 guests. Nestled on a quiet street with a big yard and private heated pool plus spa, this home is perfect fo
Hot HOT 65
5 Jessamine Place
House -
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating 5 (10)
Villamare will have a full pool and deck renovation, including the addition of a new adult-only serenity pool and hot tub, with an expected completion date of April 30, 2024. The indoor pool and hot tub will be available throughout the renovation process. Welcome and be greeted by fantastic ocean views at 1204 Villamare. This 2-bedroom villa has
Oceanfront Oceanfront
Oceanfront
1204 Villamare Icone Collection Icon
Villa -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (12)
Please be advised that the Dune House Project is set to be updated between December 2023 and January 2024 and last up to 90 days. Dune House Lane and the parking lot will be reconfigured and repaved during this project to improve pedestrian safety and allow for a better flow of traffic. Moorings guests will have access to their respective parking a
23 The Moorings
Villa -
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (8)
Penthouse 3-bed villa overlooking the world-famous Harbour Town Yacht Basin, just steps away from Harbourtown A great room with dual sofas facing a large flat-screen TV A set of sliders gives entrance to a whimsically tiled patio with a postcard-perfect view of Harbour Town, perfect for relaxing and enjoying the salt air. Those harbor views also
953 Cutter Court
Villa -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (4)
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
Hot HOT 152
1 Sandy Beach Trail Icone Collection Icon
House
Bedrooms 6 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 15 guests

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