Book Holiday Homes in Hilton Head Island

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Hilton Head Island

Marriott's Harbour Club

Marriott's Harbour Club

3.5 out of 5
144 Lighthouse Rd, Hilton Head Island, SC
Stay at this 3.5-star eco-certified vacation home in Hilton Head Island. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Coligny ...
Marriott's Harbour Club
Marriott's Heritage Club

Marriott's Heritage Club

3.5 out of 5
12 Lighthouse Lane, Hilton Head Island, SC
The price is NZ$923 per night from 12 Apr to 13 Apr
NZ$923
includes taxes & fees
12 Apr - 13 Apr
Stay at this 3.5-star eco-certified vacation home in Hilton Head Island. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Coligny ...
Marriott's Heritage Club
Guest Favorite ~FREE Heated Pool~Walk to Beach~BBQ

Guest Favorite ~FREE Heated Pool~Walk to Beach~BBQ

Hilton Head Island
Book a stay at this family-friendly vacation home in Hilton Head Island. Enjoy free WiFi, private pools, and a garden. Popular attractions Palmetto Dunes Club ...
Guest Favorite ~FREE Heated Pool~Walk to Beach~BBQ
Save an average of 15% on thousands of hotels when you're signed in
NEW LISTING ~ Luxe 6BR Marsh Retreat w/ Pool & Stunning Views ~ 31 Hearthwood Dr

NEW LISTING ~ Luxe 6BR Marsh Retreat w/ Pool & Stunning Views ~ 31 Hearthwood Dr

Hilton Head Island
Book a stay at this family-friendly vacation home in Hilton Head Island. Enjoy free WiFi, private pools, and patios. Popular attractions Coligny Plaza and Coligny ...
NEW LISTING ~ Luxe 6BR Marsh Retreat w/ Pool & Stunning Views ~ 31 Hearthwood Dr
Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown

Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown

Hilton Head Island
The price is NZ$684 per night from 24 Apr to 25 Apr
NZ$684
includes taxes & fees
24 Apr - 25 Apr
Book a stay at this beach vacation home in Hilton Head Island. Enjoy free WiFi, a beach locale, and patios. Popular attractions Coligny Plaza and Coligny Beach ...
Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown
FREE Heated Pool, Walk To Beach, Theater, Elevator

FREE Heated Pool, Walk To Beach, Theater, Elevator

Hilton Head Island
Book a stay at this family-friendly vacation home in Hilton Head Island. Enjoy free WiFi, private pools, and a garden. Popular attractions Palmetto Dunes Club ...
FREE Heated Pool, Walk To Beach, Theater, Elevator
2-Min Walk to Beach, Private Pool & Spa, Family & Dog-Friendly, Sleeps 17, Kids' Loft

2-Min Walk to Beach, Private Pool & Spa, Family & Dog-Friendly, Sleeps 17, Kids' Loft

Hilton Head Island
Book a stay at this family-friendly vacation home in Hilton Head Island. Enjoy private pools, an in-room coffeemaker, and air conditioning. Popular attractions ...
2-Min Walk to Beach, Private Pool & Spa, Family & Dog-Friendly, Sleeps 17, Kids' Loft
Ocean View, 3-Patio, 6BR, 6300sf Home w/Pool; 50 Steps to Beach, Coligny Circle!

Ocean View, 3-Patio, 6BR, 6300sf Home w/Pool; 50 Steps to Beach, Coligny Circle!

Hilton Head Isalnd
Stay at this vacation home in Hilton Head Island. Enjoy free WiFi, private pools, and tennis courts. Popular attractions Coligny Plaza and Coligny Beach are ...
Ocean View, 3-Patio, 6BR, 6300sf Home w/Pool; 50 Steps to Beach, Coligny Circle!
Hilton Head Lookout | Ocean Views| Free Heated Pool | Walk to Beach | Dog Friendly

Hilton Head Lookout | Ocean Views| Free Heated Pool | Walk to Beach | Dog Friendly

Hilton Head Island
Stay at this vacation home in Hilton Head Island. Enjoy free WiFi, private pools, and patios. Popular attractions Palmetto Dunes Club and Fish Haul Beach Park ...
Hilton Head Lookout | Ocean Views| Free Heated Pool | Walk to Beach | Dog Friendly
Don't see what you're looking for?
See all available properties in Hilton Head Island
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hilton Head Island Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Hilton Head Island vacation homes are the perfect way for you to wing it.

Holiday houses in Hilton Head Island let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Hilton Head Island in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Hilton Head Island adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Hilton Head Island with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Hilton Head Island vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Hilton Head Island Holiday Homes essential information

Accommodation
3142 Holiday Homes
Lowest Price
NZ$550
Highest Price
NZ$923
Popular accommodation
Marriott's Harbour Club, Marriott's Heritage Club, Guest Favorite ~FREE Heated Pool~Walk to Beach~BBQ, NEW LISTING ~ Luxe 6BR Marsh Retreat w/ Pool & Stunning Views ~ 31 Hearthwood Dr, Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown, FREE Heated Pool, Walk To Beach, Theater, Elevator, 2-Min Walk to Beach, Private Pool & Spa, Family & Dog-Friendly, Sleeps 17, Kids' Loft, Ocean View, 3-Patio, 6BR, 6300sf Home w/Pool; 50 Steps to Beach, Coligny Circle!, Hilton Head Lookout | Ocean Views| Free Heated Pool | Walk to Beach | Dog Friendly

Top trending hotels in Hilton Head Island

Beach House Resort Hilton Head

Beach House Resort Hilton Head

4 out of 5
1 South Forest Beach Drive, Hilton Head Island, SC
Fully refundableReserve now, pay when you stay
The price is NZ$551 per night from 21 Apr to 22 Apr
NZ$551
includes taxes & fees
21 Apr - 22 Apr
Stay at this 4-star beach hotel in Hilton Head Island. Enjoy free WiFi, a beach locale, and 2 bars/lounges. Our guests praise the restaurant and the bar in our ...
Beach House Resort Hilton Head
The Westin Hilton Head Island Resort & Spa

The Westin Hilton Head Island Resort & Spa

4 out of 5
2 Grasslawn Ave, Hilton Head Island, SC
Fully refundableReserve now, pay when you stay
The price is NZ$572 per night from 27 Apr to 28 Apr
NZ$572
includes taxes & fees
27 Apr - 28 Apr
Book a stay at this beach hotel in Hilton Head Island. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful ...
The Westin Hilton Head Island Resort & Spa
Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive, Hilton Head Island, SC
Fully refundableReserve now, pay when you stay
The price is NZ$550 per night from 22 Apr to 23 Apr
NZ$550
includes taxes & fees
22 Apr - 23 Apr
Stay at this 4-star beach hotel in Hilton Head Island. Enjoy a full-service spa, a beach locale, and breakfast (surcharge). Our guests praise the pool and the ...
Sonesta Resort Hilton Head Island
Save an average of 15% on thousands of hotels when you're signed in
Omni Hilton Head Oceanfront Resort

Omni Hilton Head Oceanfront Resort

4 out of 5
23 Ocean Lane, Hilton Head Island, SC
Fully refundableReserve now, pay when you stay
The price is NZ$657 per night from 11 May to 12 May
NZ$657
includes taxes & fees
11 May - 12 May
Stay at this 4-star beach resort in Hilton Head Island. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the bar in our reviews. ...
Omni Hilton Head Oceanfront Resort
Don't see what you're looking for?
See all available properties in Hilton Head Island
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.