Book Holiday Homes in Hilton Head Island

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Featured Holiday Homes in Hilton Head Island

One-level home, screened porch, close to beach/bike paths, dining and shopping

One-level home, screened porch, close to beach/bike paths, dining and shopping

Hilton Head Island
With a stay at this vacation home in Hilton Head Island (Sea Pines), you'll be within a 10-minute drive of Coligny Plaza and Atlantic Dunes by Davis Love ...
One-level home, screened porch, close to beach/bike paths, dining and shopping
Marriott's Heritage Club

Marriott's Heritage Club

3.5 out of 5
12 Lighthouse Lane, Hilton Head Island, SC
The price is AU$624 per night from 17 Mar to 18 Mar
AU$624
includes taxes & fees
17 Mar - 18 Mar
With a stay at Marriott's Heritage Club in Hilton Head Island (Sea Pines), you'll be within a 10-minute drive of Coligny Beach and Coligny Plaza.
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
The price is AU$1,312 per night from 24 Mar to 25 Mar
AU$1,312
includes taxes & fees
24 Mar - 25 Mar
With a stay at this vacation home in Hilton Head Island (Mid Island), you'll be within a 15-minute drive of Palmetto Dunes Club and Coligny Plaza.
Guest Favorite ~FREE Heated Pool~Walk to Beach~BBQ
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NEW: Sleeps 16+, 3rd Row, Pool, Hot Tub, Climbing Wall, Gym, Game Rm.

NEW: Sleeps 16+, 3rd Row, Pool, Hot Tub, Climbing Wall, Gym, Game Rm.

Hilton Head Island
The price is AU$2,724 per night from 30 Mar to 31 Mar
AU$2,724
includes taxes & fees
30 Mar - 31 Mar
With a stay at this vacation home in Hilton Head Island (Sea Pines), you'll be within a 5-minute drive of Coligny Beach and Coligny Plaza.
NEW: Sleeps 16+, 3rd Row, Pool, Hot Tub, Climbing Wall, Gym, Game Rm.
Sea Pines 3br-2ba - SF Home - close to everything

Sea Pines 3br-2ba - SF Home - close to everything

Hilton Head Island
Located in Hilton Head Island (Sea Pines), this vacation home is within a 10-minute drive of Coligny Beach and Coligny Plaza.
Sea Pines 3br-2ba - SF Home - close to everything
Marriott's Harbour Club

Marriott's Harbour Club

3.5 out of 5
144 Lighthouse Rd, Hilton Head Island, SC
The price is AU$624 per night from 18 Mar to 19 Mar
AU$624
includes taxes & fees
18 Mar - 19 Mar
With a stay at Marriott's Harbour Club in Hilton Head Island (Sea Pines), you'll be within a 15-minute drive of Coligny Beach and Coligny Plaza.
Marriott's Harbour Club
Shipyard Hilton Head Island

Shipyard Hilton Head Island

Hilton Head Island
With a stay at this vacation home in Hilton Head Island (South End), you'll be a 3-minute drive from Coligny Plaza and 6 minutes from Coligny Beach.
Shipyard Hilton Head Island
Sea Pines! Total renovation completed in 2022! Just a bike ride from the beach!

Sea Pines! Total renovation completed in 2022! Just a bike ride from the beach!

Hilton Head Island
With a stay at this vacation home in Hilton Head Island (Sea Pines), you'll be within a 10-minute drive of Coligny Beach and Coligny Plaza.
Sea Pines! Total renovation completed in 2022! Just a bike ride from the beach!
Charming Bluffton Home w/ Yard ~ 3 Mi to Beaches!

Charming Bluffton Home w/ Yard ~ 3 Mi to Beaches!

Bluffton
When you stay at this vacation home in Bluffton, you'll be by the sea, within a 5-minute drive of Farmers Market of Bluffton and Heyward House Historic ...
Charming Bluffton Home w/ Yard ~ 3 Mi to Beaches!
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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
2646 Holiday Homes
Lowest Price
AU$385
Highest Price
AU$2,724
Popular accommodation
One-level home, screened porch, close to beach/bike paths, dining and shopping, Marriott's Heritage Club, Guest Favorite ~FREE Heated Pool~Walk to Beach~BBQ, NEW: Sleeps 16+, 3rd Row, Pool, Hot Tub, Climbing Wall, Gym, Game Rm., Sea Pines 3br-2ba - SF Home - close to everything, Marriott's Harbour Club, Shipyard Hilton Head Island, Sea Pines! Total renovation completed in 2022! Just a bike ride from the beach!, Charming Bluffton Home w/ Yard ~ 3 Mi to Beaches!

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 AU$385 per night from 23 Mar to 24 Mar
AU$385
includes taxes & fees
23 Mar - 24 Mar
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
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 AU$681 per night from 16 Mar to 17 Mar
AU$681
includes taxes & fees
16 Mar - 17 Mar
With a stay at Omni Hilton Head Oceanfront Resort in Hilton Head Island (Mid Island), you'll be a 4-minute drive from The Golf Courses of Palmetto Dunes and ...
Omni Hilton Head Oceanfront Resort
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$401 per night from 31 Mar to 1 Apr
AU$401
includes taxes & fees
31 Mar - 1 Apr
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
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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$514 per night from 20 Mar to 21 Mar
AU$514
includes taxes & fees
20 Mar - 21 Mar
With a stay at Sonesta Resort Hilton Head Island in Hilton Head Island (South End), you'll be a 1-minute drive from Coligny Beach and 7 minutes from Coligny ...
Sonesta Resort Hilton Head Island
Don't see what you're looking for?
See all available properties in Hilton Head Island
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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.

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^Subject to availability and chosen travel dates.