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

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

Flip Flop Paradise-Steps to the Sand! Free Bikes
South End
9.8 out of 10, Exceptional, (173 reviews)
"Amazing place to vacation. Loved the view. Beach paradise extremely clean, quiet, easy beach access."
United States
Linda P.
The price is NZ$449
includes taxes & fees
17 Aug - 18 Aug
Flip Flop Paradise-Steps to the Sand! Free Bikes

2. Feelin Tip'Sea-Oceanview Retreat Steps to Beach

Feelin Tip'Sea-Oceanview Retreat Steps to Beach
South End
9.8 out of 10, Exceptional, (37 reviews)
"Yes all in all it was a great stay close to everything had a very nice time."
United States
Thomas F.
The price is NZ$442
includes taxes & fees
16 Aug - 17 Aug
Feelin Tip'Sea-Oceanview Retreat Steps to Beach

3. 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$536
includes taxes & fees
8 Sept - 9 Sept
Marriott's Harbour Point and Sunset Pointe at Shelter Cove

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

Seas the Day! Beach & Sun, with Bikes & Chairs
South End
9.6 out of 10, Exceptional, (33 reviews)
"Kendall’s place was perfect for a long weekend! Right on the ocean, walking distance to all the restaurants and shops at Coligny Beach. We had a great time and the next time we’re in Hilton Head we’ll definitely stay here again."
United States
james
The price is NZ$442
includes taxes & fees
16 Aug - 17 Aug
Seas the Day! Beach & Sun, with Bikes & Chairs

5. 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$664
includes taxes & fees
26 Aug - 27 Aug
Beachfront Condo w/ Pool Access in Hilton Head!

6. Beach Daze-Gorgeous new shower! Bikes Included

Beach Daze-Gorgeous new shower! Bikes Included
South End
9.6 out of 10, Exceptional, (30 reviews)
"Excellent location! The place was so close to the beach & walking/biking distance to shops and restaurants."
United States
Kathleen
Beach Daze-Gorgeous new shower! Bikes Included

7. 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$435
includes taxes & fees
2 Sept - 3 Sept
Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view

8. STUNNING ocean view! Brand new listing

STUNNING ocean view! Brand new listing
South End
10.0 out of 10, Exceptional, (15 reviews)
"Our host at Seaside was AMAZING!!! We enjoyed our last minute stay it was right on time for some R&R! Thank you all so lich we will be back! "
United States
Angela C.
The price is NZ$534
includes taxes & fees
27 Aug - 28 Aug
STUNNING ocean view! Brand new listing

9. Good Times and Tan Lines!-Central air, free bikes!

Good Times and Tan Lines!-Central air, free bikes!
South End
9.6 out of 10, Exceptional, (78 reviews)
"Great location "
United States
Thomas D.
Good Times and Tan Lines!-Central air, free bikes!

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

Seabatical-Beautiful ocean view! w/new bikes & Chairs
South End
10.0 out of 10, Exceptional, (90 reviews)
"We are enjoyed stay for my kids golf tournament. "
United States
Yongni G.
Seabatical-Beautiful ocean view! w/new bikes & Chairs

11. Coastal Nest - Oceanviews! Near Coligny

Coastal Nest - Oceanviews! Near Coligny
South End
9.2 out of 10, Wonderful, (18 reviews)
"We loved how close it is to the beach! "
United States
Andrea R.
The price is NZ$442
includes taxes & fees
16 Aug - 17 Aug
Coastal Nest - Oceanviews! Near Coligny

12. Crashin' Waves-Oceanview w/new bikes, Chairs& King Bed

Crashin' Waves-Oceanview w/new bikes, Chairs& King Bed
South End
9.6 out of 10, Exceptional, (178 reviews)
"Weather wasn’t good but the accommodations were good."
United States
Michael B.
The price is NZ$515
includes taxes & fees
12 Sept - 13 Sept
Crashin' Waves-Oceanview w/new bikes, Chairs& King Bed

13. Marriott's Grande Ocean

Marriott's Grande Ocean
3.5 star property
South End
9.4 out of 10, Exceptional, (177 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$953
includes taxes & fees
8 Sept - 9 Sept
Marriott's Grande Ocean

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

SeaClusion-Oceanview, Mini split AC, Beach Chairs
South End
9.8 out of 10, Exceptional, (76 reviews)
"Very conveniently located and reasonably priced. Great for a weekend couples’ getaway."
United States
Kevin W.
The price is NZ$442
includes taxes & fees
2 Sept - 3 Sept
SeaClusion-Oceanview, Mini split AC, Beach Chairs

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

SerenityByTheSea-Couples Retreat-King,Bikes,Chairs
South End
10.0 out of 10, Exceptional, (176 reviews)
"Wonderful time close to everything easy walk to the beach"
United States
charles g.
The price is NZ$455
includes taxes & fees
30 Aug - 31 Aug
SerenityByTheSea-Couples Retreat-King,Bikes,Chairs

16. 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$646
includes taxes & fees
16 Aug - 17 Aug
Walk to Beach: Hilton Head Condo w/ Pool Access

17. 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.
The price is NZ$679
includes taxes & fees
26 Aug - 27 Aug
Beachfront Condo w/ Pool Access in Hilton Head!

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

Gone Coastal! 2 from oceanfront! Central air!
South End
9.8 out of 10, Exceptional, (24 reviews)
"Loved the location!"
United States
Allison O.
Gone Coastal! 2 from oceanfront! Central air!

19. Sunset Dunes Direct Beach Access

Sunset Dunes Direct Beach Access
South End
9.8 out of 10, Exceptional, (136 reviews)
"Ideal location, great communication by host, above and beyond with all the items he provided for us. Super clean with everything we needed and more. Will def save this listing to book again"
United States
Tyler S.
Sunset Dunes Direct Beach Access

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

SeaGem-Oceanview! Steps to ocean Many Upgrades New Reno
South End
9.8 out of 10, Exceptional, (96 reviews)
"This was a great place to stay for my wife and I as we celebrated our anniversary. Beach access was great, condo was clean and the host was super helpful. I would highly recommend this for a couple or small family that wants a place that has plenty of amenities for a beach stay. "
United States
David L.
SeaGem-Oceanview! Steps to ocean Many Upgrades New Reno
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

Everything you need to know about Hilton Head Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hilton Head Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hilton Head Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hilton Head Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hilton Head Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hilton Head Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hilton Head Island holiday rentals we have selected for you start as low as NZ$536 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hilton Head Island rentals

At Expedia, we put the best Hilton Head Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hilton Head Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hilton Head Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hilton Head Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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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 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 1015 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.