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

Hilton Head Island Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Hilton Head Island holiday rentals

1. 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, (156 reviews)
"Very nice place to stay "
United States
Alejandro
The price is NZ$540
includes taxes & fees
22 Sept - 23 Sept
Marriott's Harbour Point and Sunset Pointe at Shelter Cove

2. SerenityByTheSea-Couples Retreat-King,Bikes,Chairs

SerenityByTheSea-Couples Retreat-King,Bikes,Chairs
South End
10.0 out of 10, Exceptional, (181 reviews)
"Wonderful time close to everything easy walk to the beach"
United States
charles g.
The price is NZ$496
includes taxes & fees
12 Oct - 13 Oct
SerenityByTheSea-Couples Retreat-King,Bikes,Chairs

3. Seabatical-Beautiful ocean view! w/new bikes & Chairs

Seabatical-Beautiful ocean view! w/new bikes & Chairs
South End
10.0 out of 10, Exceptional, (92 reviews)
"The room was perfect myself and my cousin. We loved how the room was right on the beach. We also enjoyed the bikes, beach chairs, toys and how close it was to Coligny beach park. Would definitely stay here again."
United States
Raven
Seabatical-Beautiful ocean view! w/new bikes & Chairs

4. 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$660
includes taxes & fees
16 Sept - 17 Sept
Beachfront Condo w/ Pool Access in Hilton Head!

5. 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

6. Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view

Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view
South End
9.6 out of 10, Exceptional, (155 reviews)
"Great location, unit was smaller than we expected it worked fine for 2 nights -right on beach perfect check in and hosts "
United States
Elizabeth
The price is NZ$450
includes taxes & fees
16 Sept - 17 Sept
Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view

7. SeaClusion-Oceanview, Mini split AC, Beach Chairs

SeaClusion-Oceanview, Mini split AC, Beach Chairs
South End
9.8 out of 10, Exceptional, (79 reviews)
"Great area location property and beach to enjoy a small getaway"
United States
Nicholas P.
The price is NZ$468
includes taxes & fees
12 Sept - 13 Sept
SeaClusion-Oceanview, Mini split AC, Beach Chairs

8. Luxury Penthouse near Beach, Tiki Hut, Coligny

Luxury Penthouse near Beach, Tiki Hut, Coligny
South End
10.0 out of 10, Exceptional, (119 reviews)
"Had a great stay. Definitely recommend."
United States
Thomas K.
The price is NZ$715
includes taxes & fees
23 Sept - 24 Sept
Luxury Penthouse near Beach, Tiki Hut, Coligny

9. 13 Forest Beach Villa/Sleeps 8/Walkable to Coligny Beach/Pool

13 Forest Beach Villa/Sleeps 8/Walkable to Coligny Beach/Pool
South End
9.6 out of 10, Exceptional, (63 reviews)
"This place is in an excellent location. Not far from Sea Pines, restaurants, and the main highway. It was clean and stocked very well with essentials. Loved staying here. "
United States
Brittanie J.
The price is NZ$544
includes taxes & fees
12 Sept - 13 Sept
13 Forest Beach Villa/Sleeps 8/Walkable to Coligny Beach/Pool

10. Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views
South End
9.4 out of 10, Exceptional, (85 reviews)
"Perfect location, check in was very easy. The condo was clean and everything exactly as it was described. Would definitely stay here again."
United States
Shane W.
Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

11. Marriott's Grande Ocean

Marriott's Grande Ocean
3.5 star property
South End
9.4 out of 10, Exceptional, (178 reviews)
"On the ocean. Family friendly."
United States
Richard
The price is NZ$961
includes taxes & fees
22 Sept - 23 Sept
Marriott's Grande Ocean

12. Coastal Calm Couples Paradise + KING Bed+ Bikes-#131

Coastal Calm Couples Paradise + KING Bed+ Bikes-#131
South End
10.0 out of 10, Exceptional, (19 reviews)
"Within steps of the ocean, great location to bike and walking trail, close to shops and dining. "
United States
Dee W.
The price is NZ$586
includes taxes & fees
17 Sept - 18 Sept
Coastal Calm Couples Paradise + KING Bed+ Bikes-#131

13. Marriott's Heritage Club

Marriott's Heritage Club
3.5 star property
Sea Pines
9.4 out of 10, Exceptional, (71 reviews)
"Great Villa! Very roomy and excellent location close to everything!"
United States
Christine
The price is NZ$589
includes taxes & fees
17 Sept - 18 Sept
Marriott's Heritage Club

14. 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$584
includes taxes & fees
13 Sept - 14 Sept
Walk to Bars & Shops: Resort Condo in Hilton Head!

15. Beachfront Condo w/ Pool Access in Hilton Head!

Beachfront Condo w/ Pool Access in Hilton Head!
South End
9.2 out of 10, Wonderful, (93 reviews)
"Ocean view was great! The pool was well maintained, warm and with a good amount of chairs. Super close to Coligny beach and shops! Loved our time there and will be back! "
United States
Gary B.
Beachfront Condo w/ Pool Access in Hilton Head!

16. Beauty at the Beach! Oceanview King bed free bikes

Beauty at the Beach! Oceanview King bed free bikes
South End
9.8 out of 10, Exceptional, (61 reviews)
"Excellent stay - the room was clean, the host was easy to communicate with and provided most everything we needed. It had a nice beach view and provided beach chairs and bikes. We would stay again."
United States
Debra B.
The price is NZ$508
includes taxes & fees
13 Sept - 14 Sept
Beauty at the Beach! Oceanview King bed free bikes

17. Oceanfront with easy beach access, large pool, and tiki bar/restaurant!

Oceanfront with easy beach access, large pool, and tiki bar/restaurant!
Mid Island
9.6 out of 10, Exceptional, (113 reviews)
"Great location, clean and host was very quick to respond."
United States
Candace D.
The price is NZ$576
includes taxes & fees
25 Sept - 26 Sept
Oceanfront with easy beach access, large pool, and tiki bar/restaurant!

18. Coastal Nest - Oceanviews! Near Coligny

Coastal Nest - Oceanviews! Near Coligny
South End
9.2 out of 10, Wonderful, (19 reviews)
"We loved how close it is to the beach! "
United States
Andrea R.
The price is NZ$453
includes taxes & fees
6 Oct - 7 Oct
Coastal Nest - Oceanviews! Near Coligny

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

Walk to Bars & Shops: Resort Condo in Hilton Head!
South End
8.8 out of 10, Excellent, (83 reviews)
"Great time, would stay again"
United States
Anonymous traveller
The price is NZ$587
includes taxes & fees
13 Sept - 14 Sept
Walk to Bars & Shops: Resort Condo in Hilton Head!

20. Beach. View. Suite. 1 br. 1 ba. Sleeps 5

Beach. View. Suite. 1 br. 1 ba. Sleeps 5
Mid Island
9.6 out of 10, Exceptional, (120 reviews)
"Would stay again!"
United States
Shandi B.
The price is NZ$452
includes taxes & fees
14 Sept - 15 Sept
Beach. View. Suite. 1 br. 1 ba. Sleeps 5
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.
Save an average of 15% on thousands of hotels when you're signed in

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there holiday rentals in Hilton Head Island?

Yes, there are holiday rentals in Hilton Head Island close to The Sandbox, 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?

Stunning Ocean View Vacation House with Private Pool, 1 Min From Beach!: This highly rated holiday home rental in Hilton Head Island offers a balcony, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind. Other favourite homes for rent in Hilton Head Island are Custom Built GORGEOUS 5 Bedroom Sea Pines Home w/ Private Pool + Screen Porch and Private Pool 4 Bedroom 2 Bathroom South Forest Beach Home! Steps to the beach!!.

How many holiday rentals are there in Hilton Head Island?

With 984 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 Sea Pines Forest Preserve and Coligny Beach are a couple of picturesque spots to enjoy the outdoors. Marine Corps Recruit Depot Parris Island and River Street 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.