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 5-night minimum for homes and a 4-night minimum for 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 135 properties available
Welcome to 101 Seacrest. This beautiful oceanfront property features three spacious bedrooms, providing ample space for a relaxing and enjoyable stay. A gorgeous foyer with a spiral staircase ascends to a massive open floor plan with open living, dining, and kitchen areas with high-end finishes and appliances. The living area is designed to be spa
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 5-night minimum for homes and a 4-night minimum for 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



101 Seacrest Icone Collection Icon
Villa -
$280.00 - $1,249.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 5 (11)
Take in the ocean views at this wonderful 1-bedroom villa. The open kitchen and living area are well-appointed to accommodate all your needs. The kitchen has been recently renovated. The dining table seats 2. The living room has a queen sleeper sofa. The primary bedroom has a queen-sized bed, and the bathroom has a walk-in shower. This villa off
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 5-night minimum for homes and a 4-night minimum for 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



212 Breakers
Villa -
$115.00 - $315.00 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Rating 5 (9)
Welcome to 253 Captain\'s Quarters, where amazing sunrises greet you in this contemporary one-bedroom villa. Coming this fall the kitchen will be renovated with new cabinets, counter tops and fixtures. The villa is designed to offer a perfect blend of modern amenities and a serene waterfront atmosphere. As you step inside, you\'re greeted by a sp
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 5-night minimum for homes and a 4-night minimum for 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



253 Captains Quarters
Villa -
$99.00 - $293.00 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Rating 4.8 (9)
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
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 5-night minimum for homes and a 4-night minimum for 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



4303 Island Club
Villa -
$119.00 - $377.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (17)
Welcome to 591 Queens Grant! This 3-bedroom, 3-bathroom villa is an end unit located in the quiet Queens Grant neighborhood in the world-class Palmetto Dunes Resort. As you enter, you are met with a fully-stocked kitchen to your right that conveniently flows into the great room of the house, consisting of the formal dining table and living area. 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 5-night minimum for homes and a 4-night minimum for 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



591 Queens Grant
Villa -
$99.00 - $278.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 4.7 (8)
1206 Sea Crest is a spacious 2nd-floor corner villa in the Sea Crest complex where you can enjoy direct oceanfront views. As you enter the front door into a small foyer, you will notice the very nice plank-style flooring. To the left is a guest bedroom with two double beds, a bench seat, and an accent chair. The sliding doors open to a private cov
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 5-night minimum for homes and a 4-night minimum for 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



1206 Seacrest
Villa -
$205.00 - $826.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 (8)
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
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 5-night minimum for homes and a 4-night minimum for 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



255 Stoney Creek | Beach Tower
Villa - Pet Friendly
$101.00 - $629.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 5 (9)
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
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 5-night minimum for homes and a 4-night minimum for 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



11 Red Oak
House -
$305.00 - $679.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 4.8 (16)
A South Forest Beach classic, this beautiful 5th row ocean home is ready to be your next relaxing beach vacation destination! Nicely appointed with many updates throughout, we know you\'ll love this very comfortable Hilton Head Island house situated just a minute or two\'s walk from beach access at the end of the street. The outdoor enthusiast wil
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 5-night minimum for homes and a 4-night minimum for 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



1 Bayberry Lane
House -
$256.00 - $1,148.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 18 guests
Rating 4.9 (13)
Welcome to this spacious and relaxing 3-bedroom home in the charming, gated community of Sea Pines. Open the door to experience a serene view of a private lagoon shaded by palm trees and live oaks dripping with Spanish moss. An abundance of natural sunlight streams in through the floor-to-ceiling windows. You will know you have arrived in the seren
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 5-night minimum for homes and a 4-night minimum for 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



35 Shell Ring
House -
$139.00 - $499.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 5 (4)
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
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 5-night minimum for homes and a 4-night minimum for 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



3 Lighthouse Road Villa Fairway Collection Icon
Villa - Pet Friendly
$96.00 - $389.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (10)
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,
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 5-night minimum for homes and a 4-night minimum for 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



301 Barrington Arms Icone Collection Icon
Villa -
$179.00 - $527.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (22)

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