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

Perfect Treehouse Escape at 2031 Deer Island in Sea Pines

Perfect Treehouse Escape at 2031 Deer Island in Sea Pines

Hilton Head Island
With a stay at this vacation home in Hilton Head Island (Sea Pines), you'll be within a 15-minute drive of Coligny Beach and Coligny Plaza.
Perfect Treehouse Escape at 2031 Deer Island in Sea Pines
Private Pool 4 Bedroom 2 Bathroom South Forest Beach Home! 2023 Remodel!

Private Pool 4 Bedroom 2 Bathroom South Forest Beach Home! 2023 Remodel!

Hilton Head Island
Located in Hilton Head Island (South End), this vacation home is steps from Coligny Beach and a 3-minute drive from Coligny Plaza.
Private Pool 4 Bedroom 2 Bathroom South Forest Beach Home! 2023 Remodel!
2 Master Suites, Water Views, bikes, kayaks, game room & short walk to beach

2 Master Suites, Water Views, bikes, kayaks, game room & short walk to beach

Hilton Head Island
With a stay at this vacation home in Hilton Head Island (South End), you'll be within a 15-minute drive of Coligny Beach and Coligny Plaza.
2 Master Suites, Water Views, bikes, kayaks, game room & short walk to beach
Save an average of 15% on thousands of hotels when you're signed in
Cozy coastal pet friendly home located in downtown Bluffton!

Cozy coastal pet friendly home located in downtown Bluffton!

Bluffton
With a stay at this vacation home in Bluffton, you'll be within a 5-minute drive of Farmers Market of Bluffton and Heyward House Historic Center.
Cozy coastal pet friendly home located in downtown Bluffton!
Recently Updated, Family-Friendly Beach Home w/ a Private Pool & Pool Spa

Recently Updated, Family-Friendly Beach Home w/ a Private Pool & Pool Spa

Hilton Head
With a stay at this vacation home in Hilton Head Island (Mid Island), you'll be a 1-minute drive from Coligny Beach and 10 minutes from Coligny Plaza.
Recently Updated, Family-Friendly Beach Home w/ a Private Pool & Pool Spa
22 Dove Street - Fantastic Updated 2nd Row Home with Ocean Views!

22 Dove Street - Fantastic Updated 2nd Row Home with Ocean Views!

Hilton Head Island
With a stay at this vacation home in Hilton Head Island (South End), you'll be steps from Coligny Beach and 8 minutes by foot from Coligny Plaza.
22 Dove Street - Fantastic Updated 2nd Row Home with Ocean Views!
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
With a stay at this vacation home in Hilton Head Island (Sea Pines), you'll be within a 15-minute drive of Coligny Plaza and Harbour Town Lighthouse.
Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown
Waterfront “State of Mind” vintage home.

Waterfront “State of Mind” vintage home.

Bluffton
When you stay at this vacation home in Bluffton, you'll be on the waterfront, within a 5-minute drive of Farmers Market of Bluffton and Heyward House Historic ...
Waterfront “State of Mind” vintage home.
Sea Pines Home on 18th Hole of Atlantic Dunes w/Private Pool & New Deck-2 DogsOK

Sea Pines Home on 18th Hole of Atlantic Dunes w/Private Pool & New Deck-2 DogsOK

Hilton Head
With a stay at this vacation home in Hilton Head Island (Sea Pines), you'll be a 3-minute drive from Coligny Beach and 6 minutes from Coligny Plaza.
Sea Pines Home on 18th Hole of Atlantic Dunes w/Private Pool & New Deck-2 DogsOK
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
2583 Holiday Homes
Lowest Price
AU$256
Highest Price
AU$306
Popular accommodation
Perfect Treehouse Escape at 2031 Deer Island in Sea Pines, Private Pool 4 Bedroom 2 Bathroom South Forest Beach Home! 2023 Remodel!, 2 Master Suites, Water Views, bikes, kayaks, game room & short walk to beach, Cozy coastal pet friendly home located in downtown Bluffton!, Recently Updated, Family-Friendly Beach Home w/ a Private Pool & Pool Spa, 22 Dove Street - Fantastic Updated 2nd Row Home with Ocean Views!, Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown, Waterfront “State of Mind” vintage home. , Sea Pines Home on 18th Hole of Atlantic Dunes w/Private Pool & New Deck-2 DogsOK

Top trending hotels in Hilton Head Island

Beach House Resort Hilton Head

Beach House Resort Hilton Head

3 out of 5
1 South Forest Beach Drive, Hilton Head Island, SC
Fully refundableReserve now, pay when you stay
The price is AU$256 per night from 19 Nov to 20 Nov
AU$256
includes taxes & fees
19 Nov - 20 Nov
With a stay at Beach House Resort Hilton Head in Hilton Head Island (South End), you'll be a 5-minute walk from Coligny Beach and 6 minutes by foot from Coligny ...
Beach House Resort Hilton Head
Hilton Beachfront Resort & Spa Hilton Head Island

Hilton Beachfront Resort & Spa Hilton Head Island

4.5 out of 5
1 Hotel Circle, Hilton Head Island, SC
Fully refundableReserve now, pay when you stay
The price is AU$306 per night from 1 Dec to 2 Dec
AU$306
includes taxes & fees
1 Dec - 2 Dec
With a stay at Hilton Beachfront Resort & Spa Hilton Head Island in Hilton Head Island (Mid Island), you'll be a 2-minute drive from Coligny Beach and 9 minutes ...
Hilton Beachfront Resort & Spa Hilton Head Island
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 AU$292 per night from 20 Nov to 21 Nov
AU$292
includes taxes & fees
20 Nov - 21 Nov
With a stay at Sonesta Resort Hilton Head Island in Hilton Head Island (South End), you'll be within a 15-minute drive of Coligny Plaza and Coligny Beach.
Sonesta Resort Hilton Head Island
Save an average of 15% on thousands of hotels when you're signed in
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 AU$306 per night from 17 Nov to 18 Nov
AU$306
includes taxes & fees
17 Nov - 18 Nov
Located in Hilton Head Island (Mid Island), The Westin Hilton Head Island Resort & Spa is within a 10-minute drive of Coastal Discovery Museum and Shelter Cove ...
The Westin Hilton Head Island Resort & Spa
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.