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 137 properties available
2517 Windsor Place is a beautifully decorated villa with 3 bedrooms and 3 baths! Perfect for a golf getaway, family vacations, and couple retreats! This villa offers bedroom separation from the living and dining areas, allowing peaceful rest for those who retire early in the evening while others have a nightcap or enjoy the views in the living area
Hot HOT 53
2517 Windsor II Icone Collection Icon
Villa -
$279.00 - $733.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4 (1)
Welcome to 1765 Bluff Villas! 1765 Bluff Villas is a stunning 3rd-floor villa in the South Beach area of Sea Pines. This completely renovated 2022 villa features comfortable furnishings in the living and dining areas. Come in to relax and take in the views. The private balcony is furnished with a table and chairs and offers scenic views of Braddoc
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Water View
1765 Bluff Villas
Villa -
$111.00 - $236.00 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Rating 5 (7)
Be Our Guest Beach Villa is proud to unveil a top-to-bottom remodel that makes it a showpiece of the Queens Grant Neighborhood. This end-unit villa offers an abundance of windows and sliding glass doors, allowing natural sunlight to flow in with views of the 11-mile lagoon system, a large stained wood deck, and a large, beautiful landscaped area n
672 Queens Grant
Villa - Pet Friendly
$165.00 - $457.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 11 guests
Rating 5 (1)
This beautiful 2-bedroom, 2-bath villa has amazing views of the ocean. The large balcony has a table, chairs, and sun loungers to soak up the view. The balcony can be accessed through the living room sliding doors and one of the bedrooms. The first bedroom has a king bed and an en suite bathroom featuring a walk-in shower and tub. Located off of t
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New Property
5303 Hampton Place
Villa -
$185.00 - $508.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 (1)
From the moment you walk through the front door, natural light comes flooding in from the windows. The living room is the perfect place to relax with its comfortable furnishings, large screen TV, and access to the balcony through a glass sliding door located by the dining table. Main level is the living area, dining room, and kitchen. Up three st
7484 Anchorage Villa
Villa -
$109.00 - $226.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)
With a scenic spot on the 11th hole, a private pool and spa to spend the day in, and spectacular views of the lagoon and golf course, this South Carolina home is the perfect vacation spot. Vaulted ceilings make this property feel comfortably spacious, which becomes even more immense when you open the sliding doors to the large deck with views of
38 Stoney Creek Road | Carolina Getaway Fairway Collection Icon
House -
$215.00 - $1,249.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (7)
Welcome to 15 Sea Lane! This Palmetto Dunes beach home features 4 bedrooms and is only a short walk to the beach—that is, if you ever want to leave this gem! 15 Sea Lane features a spacious open floor plan and plenty of natural sunlight! Unwind in the living room as you watch TV on the flatscreen or read one of your favorite novels. Plenty of seat
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New Pictures
15 Sea Lane Fairway Collection Icon
House -
$275.00 - $668.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 (11)
This spacious 3-bedroom, 2-bathroom top-floor Bluff villa is perfect for a larger family, with an open floorplan and one of the largest living spaces found in any Sea Pines villa. With six beds and room for up to two children on the sleeper sofa, this unit has everything you need for a wonderful Sea Pines vacation. The unit has a large, fully stock
1690 Bluff Villas
Villa -
$109.00 - $399.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (9)
This wonderful 3-bedroom, 3.5-bath townhouse, nicknamed "Beach Tower", is located at the entrance to Harbour Town Marina, the heart of Sea Pines Plantation. The living space has an open floor plan that includes two full-length couches and two additional chairs. The large dining table seats six, with an island seating an additional four. The kitche
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255 Stoney Creek | Beach Tower
Villa - Pet Friendly
$110.00 - $629.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 5 (8)
435 Captain\'s Walk overlooks the pool out to the ocean! Lots of recent updates! 435 Captain’s Walk is a second-floor, 3-bedroom, 3-bathroom end unit that overlooks the pool and out to the ocean. A beautiful, updated villa with great views—you couldn\'t ask for more. The new owners have added great touches and updates to make this the perfect ocea
Oceanfront Oceanfront
Oceanfront
435 Captains Walk
Villa -
$212.00 - $711.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 (16)
Welcome to 2334 Racquet Club! This renovated villa has 2 bedrooms and 2.5 baths and is located close to Harbour Town. This cozy villa has two spacious bedrooms and large closets. When you first walk in, the kitchen is open to the dining area and living room. The living room offers plenty of seating to relax after a day out in the sun. Heading upst
2334 Racquet Club
Villa -
$120.00 - $529.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 5 guests
Rating 5 (11)
Welcome to 7 Rum Row! This Palmetto Dunes home highlights coastal elegance with plenty of room for the whole family to spread out while all being together. The living room, dining area, and kitchen all make up the main great room, and the extremely open floor plan makes it easy for everyone to be together without feeling crowded! The living room i
Hot HOT 69
7 Rum Row Fairway Collection Icon
House -
$265.00 - $616.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 5 (14)

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