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 142 properties available
For a group that enjoys golf, a stay at the high-end Stoney Creek house cannot be topped! This single-level home is adjacent to the Heron Point Golf Course, and the expansive back deck offers an impressive view of the 10th fairway. Plus, you\'ll have fun making a splash in the private spa and pool, complete with a basketball hoop. Slip through on
60 Stoney Creek Road Fairway Collection Icon
House -
$258.00 - $1,459.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 11 guests
Rating 4.9 (17)
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
28 Corine Lane
House - Pet Friendly
$214.00 - $813.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 15 guests
Rating 4.8 (12)
This magnificently remodeled North Shore Place villa features two bedrooms. Walking into an open-concept floor plan. The master bedroom has a beautiful king bed and private ensuite bath. The ensuite bathroom features a walk-in shower. The guest bedroom has a queen bed. The guest bathroom has a shower and tub combination. A rooftop pool and hot t
103 North Shore Place
Villa -
$135.00 - $426.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (11)
You\'re going to love this Barrington Arms villa, completely renovated in 2021. This pristine 3rd floor (end unit) villa is wonderfully furnished and overlooks the landscaped gardens and pool out to the Atlantic Ocean! The well-appointed kitchen is fully equipped and has been renovated with granite countertops, brand new cabinets, and appliances,
Hot HOT 100
301 Barrington Arms Icone Collection Icon
Villa -
$179.00 - $654.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (24)
Welcome to 2519 Windsor. This gorgeous oceanfront 3-bedroom, 3-bathroom villa is perfect for your next getaway. Experience the ultimate beachfront retreat in this stunning 3-bedroom villa on Hilton Head Island. Located on the top floor, you\'ll enjoy breathtaking ocean views and the soothing sounds of the tides. The villa features two pools for
2519 Windsor II
Villa -
$239.00 - $788.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (12)
Located in Palmetto Dunes and only a few minutes walk to the beach, this four bedroom home has all you need for the perfect stay on the island. 3 Cartgate offers four bedrooms and four and a half bathrooms, large spacious rooms, an open kitchen and private pool! As you walk into the home, the first floor features a spacious living room that connec
3 Cartgate
House -
$270.00 - $892.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 5 (2)
3 bedroom remodeled villa in Palmetto Dunes, with an extra-large deck overlooking the 2nd hole of Robert Trent Jones Oceanfront Golf Course and lush views of the lagoon. This two-story villa has all new furniture and renovated kitchens and bathrooms. The primary bedroom on the first floor has a king bed and a large en-suite bathroom with a designe
756 Queens Grant Fairway Collection Icon
Villa -
$125.00 - $366.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 7 guests
Rating 5 (3)
This spacious home embodies beach cottage vibes with its open layout and tastefully decorated interior! Soaring ceilings and lots of windows provide the great room with plenty of natural sunlight. In the living room, you will find plenty of plush seating around the brick fireplace (not for guest use), a flat-screen TV, and an array of board games t
31 Sand Dollar Road
House - Pet Friendly
$184.00 - $846.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 4.8 (8)
512 Shorewood is a spectacular 3-bedroom, 3-bathroom oceanfront villa with beach views! This stunning beach condo sleeps 8 and is on the 5th floor with elevator access, featuring all new furniture and décor with an incredible ocean view from every room, a community pool, beach access, and more! Upon entering, you are met with views from the kitc
Oceanfront Oceanfront
Oceanfront
512 Shorewood Place Icone Collection Icon
Villa -
$329.00 - $1,279.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (10)
2390 Lighthouse Tennis Villa invites you to experience the Sea Pines Community on Hilton Head Island. In addition to its premier location surrounded by beautiful scenery, this well-appointed villa is an exceptional getaway retreat. From Harbour Town Marina to South Beach, 2390 Lighthouse Villa has something for anyone wanting to come enjoy the sand
2390 Lighthouse Tennis
Villa - Pet Friendly
$115.00 - $337.00 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Rating 4.7 (9)
3 Bedroom Villa in Harbour Town Area, Newly Renovated, and Golf View Gorgeous renovations in 2020 make this villa the right choice for you. As you enter, you are greeted with a two-story, open, and airy space. This open-concept living, dining, and kitchen area is perfect for entertaining or relaxing with all the family. With windows all along the
2371 Racquet Club Fairway Collection Icon
Villa -
$218.00 - $699.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (8)
Indulge in the tranquil charm of a beach vacation at 25 Singleton Beach, a grand and luxurious 7-bedroom retreat designed for unforgettable seaside getaways. This stunning brand-new home boasts large glass doors and windows that flood the interior with natural light and frame breathtaking views of Hilton Head’s pristine coastline. Each room is thou
25 Singleton Beach Icone Collection Icon
House
$1,099.00 - $3,353.00 / per night
Bedrooms 7 bedrooms
Bathrooms 7 baths
Half Bathrooms 1 half bath
Guests 17 guests

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