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 SurfWatch

Marriott's SurfWatch
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (202 reviews)
"Great resort, great room "
United States
Crista
The price is NZ$873
includes taxes & fees
18 Sept - 19 Sept
Marriott's SurfWatch

2. 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$582
includes taxes & fees
18 Sept - 19 Sept
Marriott's Heritage Club

3. 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

4. Ocean Palms Villas at Port Royal Resort

Ocean Palms Villas at Port Royal Resort
3.5 star property
Mid Island
8.6 out of 10, Excellent, (98 reviews)
"It was perfect for our needs. Check-in was super easy!"
United States
Melanie
The price is NZ$734
includes taxes & fees
16 Sept - 17 Sept
Ocean Palms Villas at Port Royal Resort

5. Steps to Beach-hilton Head Condo-pet Friendly

Steps to Beach-hilton Head Condo-pet Friendly
2.0 star property
Mid Island
The price is NZ$945
includes taxes & fees
21 Sept - 22 Sept
Steps to Beach-hilton Head Condo-pet Friendly

6. 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$3,052
includes taxes & fees
7 Oct - 8 Oct
Montage Palmetto Bluff Residences

7. 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$602
includes taxes & fees
13 Sept - 14 Sept
Walk to Bars & Shops: Resort Condo in Hilton Head!

8. Marriott's Barony Beach Club

Marriott's Barony Beach Club
3.5 star property
Mid Island
9.4 out of 10, Exceptional, (252 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$866
includes taxes & fees
16 Sept - 17 Sept
Marriott's Barony Beach Club

9. 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$582
includes taxes & fees
22 Sept - 23 Sept
Marriott's Harbour Club

10. 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$769
includes taxes & fees
29 Sept - 30 Sept
Marriott's Monarch at Sea Pines

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$949
includes taxes & fees
22 Sept - 23 Sept
Marriott's Grande Ocean

12. 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$537
includes taxes & fees
20 Sept - 21 Sept
Marriott's Harbour Point and Sunset Pointe at Shelter Cove

13. 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
Walk to Beach: Hilton Head Condo w/ Pool Access

14. 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$634
includes taxes & fees
19 Sept - 20 Sept
Palmetto Dunes Golf Getaway: Pool + Beach Access!

15. Oceanfront Breakers 137 Condo w/ Sunrise Views!

Oceanfront Breakers 137 Condo w/ Sunrise Views!
4.0 star property
South End
The price is NZ$715
includes taxes & fees
4 Oct - 5 Oct
Oceanfront Breakers 137 Condo w/ Sunrise Views!

16. Serene Hilton Head Island Condo w/ Community Pool!

Serene Hilton Head Island Condo w/ Community Pool!
4.0 star property
South End
The price is NZ$739
includes taxes & fees
18 Sept - 19 Sept
Serene Hilton Head Island Condo w/ Community Pool!

17. Savannah Oasis Hot Tub Pickleball Putt Putt

Savannah Oasis Hot Tub Pickleball Putt Putt
2.0 star property
Whitemarsh Island
The price is NZ$901
includes taxes & fees
8 Oct - 9 Oct
Savannah Oasis Hot Tub Pickleball Putt Putt

18. The Grant by Black Swan

The Grant by Black Swan
2.0 star property
Historic Downtown Savannah
9.2 out of 10, Wonderful, (364 reviews)
"Central to everything Fun."
United States
Beverly Edenfield
The price is NZ$305
includes taxes & fees
10 Sept - 11 Sept
The Grant by Black Swan

19. Kasa Jules Savannah

Kasa Jules Savannah
4.0 star property
Historic Downtown Savannah
9.2 out of 10, Wonderful, (133 reviews)
"The place is incredible, a hidden jem and I would stay there every time I came to Savannah!"
United States
Jeff
The price is NZ$278
includes taxes & fees
10 Sept - 11 Sept
Kasa Jules Savannah

20. The Juliette by AvantStay

The Juliette by AvantStay
3.0 star property
Historic Downtown Savannah
9.8 out of 10, Exceptional, (17 reviews)
"Excellent property, well located, beautifully decorated. Easy check in and check out. Recommended!!"
United States
Gabriel
The price is NZ$456
includes taxes & fees
23 Sept - 24 Sept
The Juliette by AvantStay
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?

Custom Built GORGEOUS 5 Bedroom Sea Pines Home w/ Private Pool + Screen Porch: 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 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Hilton Head Island are Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380 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 1017 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.