A coastal town with a lighthouse, marina, and golf course.

Hilton Head Island Holiday Rentals

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Our top choices for Hilton Head Island holiday rentals

Marriott's SurfWatch

Marriott's SurfWatch
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (199 reviews)
"Great resort, great room "
United States
Crista
The price is NZ$1,340
includes taxes & fees
22 Aug - 23 Aug
Marriott's SurfWatch

Marriott's Harbour Club

Marriott's Harbour Club
3.5 star property
Sea Pines
9.0 out of 10, Wonderful, (63 reviews)
"Clean and spacious. Very convenient location. "
United States
CLAUDIA
The price is NZ$872
includes taxes & fees
10 Aug - 11 Aug
Marriott's Harbour Club

Disney's Hilton Head Island Resort

Disney's Hilton Head Island Resort
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (131 reviews)
"The room and property were incredible! Already booking my next stay"
United States
Melissa
Disney's Hilton Head Island Resort

Montage Palmetto Bluff Residences

Montage Palmetto Bluff Residences
5.0 star property
Palmetto Bluff
10.0 out of 10, Exceptional, (2 reviews)
"Very family friendly. Parking was a problem Check in was not one minute early. House was beautiful and very clean. Pool was wonderful Prices were high but we knew that ahead of time"
United States
john j
The price is NZ$2,858
includes taxes & fees
27 July - 28 July
Montage Palmetto Bluff Residences

Pool Time & Island Vibes! Hilton Head Getaway

Pool Time & Island Vibes! Hilton Head Getaway
3.0 star property
Mid Island
The price is NZ$704
includes taxes & fees
5 Aug - 6 Aug
Pool Time & Island Vibes! Hilton Head Getaway

Marriott's Grande Ocean

Marriott's Grande Ocean
3.5 star property
South End
9.4 out of 10, Exceptional, (175 reviews)
"Great beach. Many pools. Very spacious bedrooms, living room and full kitchen. Large bathrooms. Lots of activities. Would have liked a restaurant on property for breakfast. Marriott needs to spend a few more bucks on toilet paper (not a joke)."
United States
Susan
The price is NZ$1,365
includes taxes & fees
21 Aug - 22 Aug
Marriott's Grande Ocean

Marriott's Heritage Club

Marriott's Heritage Club
3.5 star property
Sea Pines
9.4 out of 10, Exceptional, (69 reviews)
"Great Villa! Very roomy and excellent location close to everything!"
United States
Christine
The price is NZ$738
includes taxes & fees
23 Aug - 24 Aug
Marriott's Heritage Club

Beachfront Condo w/ Pool Access in Hilton Head!

Beachfront Condo w/ Pool Access in Hilton Head!
4.0 star property
South End
9.0 out of 10, Wonderful, (2 reviews)
"Poor sofa searing. Sits very low and to very soft."
United States
Roger
The price is NZ$666
includes taxes & fees
26 July - 27 July
Beachfront Condo w/ Pool Access in Hilton Head!

Marriott's Monarch at Sea Pines

Marriott's Monarch at Sea Pines
3.0 star property
Sea Pines
9.2 out of 10, Wonderful, (132 reviews)
"Loved this property "
United States
Sharon
The price is NZ$1,320
includes taxes & fees
25 Aug - 26 Aug
Marriott's Monarch at Sea Pines

Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Marriott's Harbour Point and Sunset Pointe at Shelter Cove
3.5 star property
Mid Island
9.2 out of 10, Wonderful, (154 reviews)
"Very nice place to stay "
United States
Alejandro
The price is NZ$659
includes taxes & fees
23 Aug - 24 Aug
Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Marriott's Barony Beach Club

Marriott's Barony Beach Club
3.5 star property
Mid Island
9.4 out of 10, Exceptional, (251 reviews)
"Family orientated hotel with great pools, walk on beach access, wonderful BBQ options for self catering. Rooms are large and family orientated. Fab stay! "
Australia
Pauline
The price is NZ$1,236
includes taxes & fees
23 Aug - 24 Aug
Marriott's Barony Beach Club

Private Beach Access: Hilton Head Island Condo!

Private Beach Access: Hilton Head Island Condo!
3.0 star property
Mid Island
10.0 out of 10, Exceptional, (3 reviews)
"The condo was cute, clean and cozy. Lots of amenities in the complex, didn't have to leave the property all day! There was even.live music "
United States
Elizabeth
The price is NZ$549
includes taxes & fees
29 July - 30 July
Private Beach Access: Hilton Head Island Condo!

Oceanfront Hilton Head Island Condo w/ Pool!

Oceanfront Hilton Head Island Condo w/ Pool!
3.0 star property
South End
9.0 out of 10, Wonderful, (4 reviews)
"Nice!! Location great, easy instructions on entry access, nice side view of the ocean from the balcony, the host Meagan was so very nice and accommodating, very close to restaurants and stores, would love to stay here again, Thanks a million!!!! ;)"
United States
Beverly
The price is NZ$649
includes taxes & fees
30 July - 31 July
Oceanfront Hilton Head Island Condo w/ Pool!

Walk to Hilton Head Island Beach: Villa w/ Balcony

Walk to Hilton Head Island Beach: Villa w/ Balcony
3.5 star property
South End
6.0 out of 10, (1 review)
"Enjoyed myself "
United States
Leviticus
Walk to Hilton Head Island Beach: Villa w/ Balcony

Walk to Bars & Shops: Resort Condo in Hilton Head!

Walk to Bars & Shops: Resort Condo in Hilton Head!
3.5 star property
South End
The price is NZ$617
includes taxes & fees
29 July - 30 July
Walk to Bars & Shops: Resort Condo in Hilton Head!

Walk to Beach: Hilton Head Condo w/ Pool Access

Walk to Beach: Hilton Head Condo w/ Pool Access
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (5 reviews)
"Very clean and easy access to the beach "
United States
LUMINITA
The price is NZ$669
includes taxes & fees
12 Aug - 13 Aug
Walk to Beach: Hilton Head Condo w/ Pool Access

Palmetto Dunes Golf Getaway: Pool + Beach Access!

Palmetto Dunes Golf Getaway: Pool + Beach Access!
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (1 review)
"Communication with owner is excellent and villa is located in great location "
United States
minoshka
The price is NZ$643
includes taxes & fees
11 Aug - 12 Aug
Palmetto Dunes Golf Getaway: Pool + Beach Access!

Pools, Beach Access: South Carolina Retreat!

Pools, Beach Access: South Carolina Retreat!
3.0 star property
Mid Island
8.0 out of 10, Very good, (7 reviews)
"Absolutely loved and enjoyed staying here. Was a clean and very enjoyable experience. Just as described. Will definitely recommend and would love to be back. Thank you "
United States
Laura
The price is NZ$589
includes taxes & fees
5 Aug - 6 Aug
Pools, Beach Access: South Carolina Retreat!

Oceanfront Condo! Breakers 210 w/ Sunrise Views

Oceanfront Condo! Breakers 210 w/ Sunrise Views
4.0 star property
South End
The price is NZ$810
includes taxes & fees
27 July - 28 July
Oceanfront Condo! Breakers 210 w/ Sunrise Views

Pool & Folly Field Beach Access! HHI Resort Condo

Pool & Folly Field Beach Access! HHI Resort Condo
3.0 star property
Mid Island
The price is NZ$607
includes taxes & fees
10 Aug - 11 Aug
Pool & Folly Field Beach Access! HHI Resort Condo
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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Top Hilton Head Island Hotel Reviews

Find out more about Hilton Head Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Hilton Head Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Hilton Head Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Hilton Head Island. Seeing all the best attractions is bound to make you fall in love with Hilton Head Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Hilton Head Island short-term rentals, that won’t be hard to do.

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Frequently asked questions

Are there holiday rentals in Hilton Head Island?

Yes, there are holiday rentals in Hilton Head Island close to Arts Center of Coastal Carolina, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the scenic seaside and waterfront in Hilton Head Island. Make sure you have time to check out the golf courses while you're in the area.

What are some of the best holiday rentals that Hilton Head Island has to offer?

Beautiful Palmetto Dunes Vacation Home with Private Pool & Outdoor Living, 5 Min To Beach: This highly rated holiday home rental in Hilton Head Island offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books. Other favourite homes for rent in Hilton Head Island are Spacious Upscale Home with Direct Private Access to the Beach and Heated Pool! and Backyard pickleball. Private Pool. Large family home! Custom Outdoor kitchen..

How many holiday rentals are there in Hilton Head Island?

With 989 Expedia holiday rentals, you're guaranteed to find just the right place for your Hilton Head Island stay.

What’s there to see and do in Hilton Head Island?

Cultural attractions include Arts Center of Coastal Carolina and Coastal Discovery Museum, whereas Coligny Beach and Sea Pines Forest Preserve are a couple of picturesque spots to enjoy the outdoors. Tybee Island Beach and Marine Corps Recruit Depot Parris Island are other popular places to visit in the area.

What’s a holiday rental in Hilton Head Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hilton Head Island. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.