Hilton Head Island Holiday Rentals from NZ$528: Search Short-Term Rentals

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. Flip Flop Paradise-Steps to the Sand! Free Bikes

South End

Linda P.

2. Coastal Nest - Oceanviews! Near Coligny

South End

Andrea R.

3. Seas the Day! Beach & Sun, with Bikes & Chairs

South End

Viktoriya P.

includes taxes & fees

24 Aug - 25 Aug

4. Beach Daze-Gorgeous new shower! Bikes Included

South End

Kathleen

includes taxes & fees

24 Aug - 25 Aug

5. STUNNING ocean view! Brand new listing

South End

Angela C.

includes taxes & fees

23 Aug - 24 Aug

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

South End

Elizabeth

includes taxes & fees

1 Sept - 2 Sept

Apartment (1 Bedroom) | Front of property

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

South End

Roger

includes taxes & fees

26 Aug - 27 Aug

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

South End

Yongni G.

includes taxes & fees

18 Sept - 19 Sept

View all properties

Find holiday rentals that suit your style

Private holiday homes

Condos

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Hilton Head Island Hotel Reviews

Courtyard by Marriott Hilton Head Island

10/10 Excellent

"Wonderful stay, clean, beds were awesome, loved the pool, live music. Had a very relaxed stay. Will stay again if I get the opportunity"

Doubletree by Hilton Hilton Head Island

8/10 Good

"Rooms were small for the price. You have to pay extra for breakfast, website says buffet but you order off the menu in the restaurant at a $15 limit, after that you pay the rest. Only 2 things on menu were $15 or under. If I would of know this before hand, I wouldn't of paid for the breakfast. Hotel is right by a beach access."

Spark By Hilton Hilton Head Island

8/10 Good

"MopThe property was well kept, the staff were helpful, breakfast was nutritional, but the juice was left sitting out, and it was room temperature which I would have preferred to be cold. The hotel had a $10 a day parking fee which I thought should have been free for the customers. The beach wasn't far, and the hotel did have a shuttle to transport customer's to the beach, but if you preferred to drive your own vehicle there was pay parking near the beach $3.35 during the week, and $5.35 on the weekend, but they close at 5 p.m, so be prepared if you're driving your vehicle and want to spend the day at the beach. It's a nice place, but if I could say anything to the management, it would be that an air vent installed in the bathroom would be a plus for this property. I would recommend this hotel, great place to go."

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 popular beaches 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?

Spacious Upscale Home with Direct Private Access to the Beach and Heated Pool!: This highly rated holiday home rental in Hilton Head Island is located on the beach, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade/games room. Another good choice for your trip to Hilton Head Island is Custom Built GORGEOUS 5 Bedroom Sea Pines Home w/ Private Pool + Screen Porch.

How many holiday rentals are there in Hilton Head Island?

With 1031 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. 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.

Hilton Head Island Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Hilton Head Island holiday rentals

1. Flip Flop Paradise-Steps to the Sand! Free Bikes

2. Coastal Nest - Oceanviews! Near Coligny

3. Seas the Day! Beach & Sun, with Bikes & Chairs

4. Beach Daze-Gorgeous new shower! Bikes Included

5. STUNNING ocean view! Brand new listing

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

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

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

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

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

11. SeaGem-Oceanview! Steps to ocean Many Upgrades New Reno

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

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

14. Gone Coastal! 2 from oceanfront! Central air!

15. Beautiful Couples Retreat Oceanview w/new bikes&Chairs

16. Coastal Getaway: Oceanview Condo in Hilton Head

17. OceanEscape – Steps to the Beach

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

19. Just Beachy! Absolute top notch design, Oceanviews

20. Shore Beats Work!-Stunning view 3 from oceanfront new bikes Incl.

Find holiday rentals that suit your style

Top Hilton Head Island Hotel Reviews

Courtyard by Marriott Hilton Head Island

Find out more about Hilton Head Island

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app