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
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138 properties available
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
4303 Island Club
Villa -
$129.00 - $450.00 / per night
2
bedrooms
2
baths
6
guests
5
(16)
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](/images/layout/fairway-collection-logo.jpg)
House -
$259.00 - $1,249.00 / per night
3
bedrooms
3
baths
8
guests
5
(9)
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
1584 Lagoon Villas
Villa -
$159.00 - $434.00 / per night
2
bedrooms
2
baths
6
guests
5
(4)
Welcome to 13 Sea Lane! This stunning Palmetto Dunes beach home has recently undergone a full renovation, boasting 5 bedrooms and offering a short stroll to both the beach and the Robert Trent Jones Golf Course. The highlight of this retreat is the brand new private pool, perfect for unwinding and soaking up the Hilton Head Island sunshine.
Step i
13 Sea Lane
![Fairway Collection Icon](/images/layout/fairway-collection-logo.jpg)
House -
$329.00 - $1,358.00 / per night
5
bedrooms
5
baths
1
half bath
16
guests
5
(5)
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
89 The Moorings
Villa -
$119.00 - $423.00 / per night
2
bedrooms
3
baths
8
guests
4.8
(14)
This stunningly decorated 2-bedroom villa is just steps away from Harbourtown. The open-concept living space offers breathtaking views of the Calibogue Sound. Walking in on the first level, you are met with a spacious living room with comfy couches. Open to the living room is the dining area, which has an adjacent bar cart and seats six comfortably
729 Schooner Court
Villa -
$159.00 - $556.00 / per night
2
bedrooms
2
baths
1
half bath
4
guests
4.8
(10)
Welcome to the 11 Red Oak! This Sea Pines home is nestled on a quiet street and places you only minutes away from Harbour Town and the sandy beaches!
Upon entry, you walk into the sitting room, which has plenty of comfortable seating around the cozy brick fireplace (not for guest use). Soaring ceilings and many large windows produce a light and ai
11 Red Oak
House -
$329.00 - $679.00 / per night
3
bedrooms
2
baths
1
half bath
8
guests
4.8
(16)
Brand New Construction 3rd row home in Palmetto Dunes!
130 Mooring Buoy is a beautiful 5-bedroom, 4.5-bath luxury home nestled in the beautiful Palmetto Dunes Oceanfront Resort. Just three rows from the beach, this home is meticulously designed for your perfect vacation.
With an open first-floor layout, the entire family can spread out without mi
130 Mooring Buoy
![Icone Collection Icon](/images/layout/icone-collection-icon.png)
House -
$599.00 - $1,973.00 / per night
5
bedrooms
4
baths
1
half bath
14
guests
5
(8)
Welcome to 26 Bradley Circle!
Views, views, and more views! What better way to start your day than listening to the surf, enjoying the beautiful scenery of the marsh with active wildlife, and the ocean just beyond while sipping your coffee on the deck? An expansive, gorgeous beach is just a 1-minute walk away! 26 Bradley is the perfect location o
26 Bradley Circle
House -
$333.00 - $1,473.00 / per night
5
bedrooms
5
baths
16
guests
5
(6)
Welcome to 36 Red Oak! This pet-friendly Sea Pines home has an extremely open floor plan with soaring ceilings to create a charming environment perfect for your next vacation. Three bedrooms and three bathrooms offer enough space to host up to 10 guests comfortably. Multiple living and sitting spaces with brand new flatscreen TVs offer plenty of sp
36 Red Oak
![Fairway Collection Icon](/images/layout/fairway-collection-logo.jpg)
House -
$239.00 - $1,219.00 / per night
3
bedrooms
3
baths
12
guests
5
(9)
Beautiful 3-bedroom villa with 3 full baths So close to the truly spectacular beaches of Palmetto Dunes Remodeled kitchen and baths Oversized covered deck overlooking the community pool.
Overlooking the Fazio Golf Course in Palmetto Dunes, this spacious, newly updated townhouse is ready to be your next home-away-from-home for your vacation to Hilt
57 Fazio Villas
![Fairway Collection Icon](/images/layout/fairway-collection-logo.jpg)
Villa -
$117.00 - $410.00 / per night
3
bedrooms
3
baths
7
guests
4.8
(9)
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! 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 the large windows and slid
6 East Garrison
House -
$249.00 - $680.00 / per night
3
bedrooms
2
baths
8
guests
5
(13)
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