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 3-night minimum for homes and 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




Properties Available 128 properties available
Welcome to 233 Turnberry. This spectacular villa has been renovated with new flooring, painting, and furniture. Walking into the villa welcomes you to an open-concept living area featuring high ceilings and large windows that bathe the space in natural light. The living room is elegantly furnished, creating a comfortable yet sophisticated ambianc
Specials Tag Special
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 3-night minimum for homes and 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



233 Turnberry Villas Fairway Collection Icon
Villa -
$118.00 - $354.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (2)
This 7,500-square-foot beachfront home features a private, in-ground pool with a spa and a patio overlooking the Atlantic Ocean. With private beach access, this home is perfect for those long beach days! The kitchen is equipped with stainless steel appliances, a split, two-sink granite island set, and ample countertop space, so there\'s plenty of r
Specials Tag Special
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 3-night minimum for homes and 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



23 Black Skimmer Icone Collection Icon
House -
$1,199.00 - $6,404.00 / per night
Bedrooms 8 bedrooms
Bathrooms 9 baths
Half Bathrooms 1 half bath
Guests 26 guests
Rating 5 (7)
9 Armada is a gorgeous second row home directly on the beach path in Palmetto Dunes Resort. This spacious 6,800 square foot home is perfect for entertaining, dining, reading, or relaxing! The kitchen features granite counters, two sinks, two dishwashers, a warming drawer, a wine cooler, and bar seating. The kitchen opens to the dining area and gre
Specials Tag Special
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 3-night minimum for homes and 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



9 Armada Icone Collection Icon
House -
$754.00 - $2,984.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half Bathrooms 1 half bath
Guests 19 guests
Rating 5 (3)
Welcome to 40 Hickory Cove. Located in Palmetto Dunes, it is just steps away from the community pool and a short walk to the beach. The villa features two bedrooms and three bathrooms, providing ample space. Upon entering, you find yourself in a bright and open living room, characterized by large windows that allow ample natural light to fill the
Specials Tag Special
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 3-night minimum for homes and 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



40 Hickory Cove
Villa - Pet Friendly
$135.00 - $301.00 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (6)
This amazing island getaway is nestled among the pines beside a lagoon on 1.9 acres in the heart of Sea Pines. This beach home offers beautiful high-end finishes in the huge eat-in kitchen and throughout, including the spacious dining room, living room, and first-floor master suite. The media room, bedrooms, and bathrooms are luxurious and comfort
Specials Tag Special
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 3-night minimum for homes and 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



5 Calibogue Cay
House - Pet Friendly
$236.00 - $1,150.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 10 guests
Rating 5 (3)
Welcome to 6 Grey Widgeon! This breath-taking 4th-row home is one of a kind and has everything you need and more for your next Hilton Head vacation. The great room is spacious and is sure to keep guests feeling right at home with its stylish but cozy furnishings! Soaring ceilings and huge windows allow plenty of natural sunlight to shine through
Specials Tag Special
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 3-night minimum for homes and 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



6 Grey Widgeon Icone Collection Icon
House -
$409.00 - $1,827.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 16 guests
Rating 4.9 (12)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 510 Mainsail is a gorgeous two-bedroom, two-and-a-half-bath, top-floor villa with breathtaking panoramic views of Shelter Cove Harbour. Designer-decorated, this property is perfect for a Hilton Head vacation and comfortably accommodates up to four people. Th
Specials Tag Special
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 3-night minimum for homes and 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



510 Mainsail
Villa -
$164.00 - $503.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 6 guests
Rating 5 (7)
This exquisite 4-bedroom, 4-bathroom vacation home is a new addition to the market, located in the prestigious Palmetto Dunes, acclaimed for its natural beauty and diverse amenities on Hilton Head Island, South Carolina. Freshly renovated with meticulous attention to detail, this house reflects a seamless blend of modern comfort and lowcountry cha
Specials Tag Special
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 3-night minimum for homes and 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



27 Starboard Tack
House -
$282.00 - $1,112.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 5 (6)
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 3-minute walk away! 26 Bradley is the perfect location o
Specials Tag Special
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 3-night minimum for homes and 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



26 Bradley Circle
House - Pet Friendly
$336.00 - $1,527.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 16 guests
Rating 5 (6)
The beach is calling at 62 Mooring Buoy! This sun-filled home is located in beautiful Palmetto Dunes, just a one-minute walk to the beach for toes in the sand. No crossing of streets, located on the beach path! Featuring 4 bedrooms and 4 baths, there is plenty of room for the entire family. Relax in the light-filled, open-concept kitchen or great
Specials Tag Special
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 3-night minimum for homes and 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



62 Mooring Buoy
House -
$389.00 - $1,385.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.9 (34)
Welcome to 12 Cassina Lane! This oceanfront stunner is located in South Forest Beach to offer panoramic ocean views and places you only minutes away from fun at Coligny Plaza. Upon entry, you walk into the first-floor great room of the home, which consists of a living room, kitchenette, and dining area. The living room has plenty of seating around
Specials Tag Special
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 3-night minimum for homes and 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



12 Cassina Lane Icone Collection Icon
House -
$629.00 - $2,729.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 12 guests
Rating 4.8 (12)
This charming Palmetto Dunes home offers expansive golf course views and features multiple living spaces to host large groups with ease. On the main level, the living room offers comfortable seating around the flatscreen TV and fireplace, as well as direct views of and access to the private pool and deck. An open floor plan allows an easy flow to
Specials Tag Special
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 3-night minimum for homes and 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



176 Mooring Buoy Fairway Collection Icon
House -
$310.00 - $1,518.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 2 half baths
Guests 12 guests
Rating 4.8 (17)

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