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

Seas the Day! Beach & Sun, with Bikes & Chairs
South End
9.6 out of 10, Exceptional, (34 reviews)
"Hilton Was amazing"
United States
Viktoriya P.
Seas the Day! Beach & Sun, with Bikes & Chairs

2. 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
The price is NZ$449
includes taxes & fees
4 Sept - 5 Sept
Beach Daze-Gorgeous new shower! Bikes Included

3. 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$515
includes taxes & fees
27 Aug - 28 Aug
STUNNING ocean view! Brand new listing

4. 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$570
includes taxes & fees
28 Aug - 29 Aug
Walk to Bars & Shops: Resort Condo in Hilton Head!

5. 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$431
includes taxes & fees
20 Sept - 21 Sept
Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view

6. Beachy Keen Seaside Villa Near Coligny W/Bikes!

Beachy Keen Seaside Villa Near Coligny W/Bikes!
South End
9.8 out of 10, Exceptional, (90 reviews)
"Great stay!"
United States
Katleen M.
The price is NZ$440
includes taxes & fees
3 Sept - 4 Sept
Beachy Keen Seaside Villa Near Coligny W/Bikes!

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

Seabatical-Beautiful ocean view! w/new bikes & Chairs
South End
10.0 out of 10, Exceptional, (91 reviews)
"We are enjoyed stay for my kids golf tournament. "
United States
Yongni G.
The price is NZ$445
includes taxes & fees
30 Aug - 31 Aug
Seabatical-Beautiful ocean view! w/new bikes & Chairs

8. 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$467
includes taxes & fees
23 Sept - 24 Sept
SeaClusion-Oceanview, Mini split AC, Beach Chairs

9. 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!

10. 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, (98 reviews)
"Great condo and access to the beach."
United States
Jane L.
The price is NZ$462
includes taxes & fees
30 Aug - 31 Aug
SeaGem-Oceanview! Steps to ocean Many Upgrades New Reno

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

SerenityByTheSea-Couples Retreat-King,Bikes,Chairs
South End
10.0 out of 10, Exceptional, (179 reviews)
"Wonderful time close to everything easy walk to the beach"
United States
charles g.
The price is NZ$464
includes taxes & fees
30 Aug - 31 Aug
SerenityByTheSea-Couples Retreat-King,Bikes,Chairs

12. 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, (82 reviews)
"Great time, would stay again"
United States
Anonymous traveller
The price is NZ$565
includes taxes & fees
28 Aug - 29 Aug
Walk to Bars & Shops: Resort Condo in Hilton Head!

13. 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)
"Great stay- host was very responsive to questions!"
United States
Kayla H.
The price is NZ$519
includes taxes & fees
25 Aug - 26 Aug
Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

14. 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$645
includes taxes & fees
26 Aug - 27 Aug
Beachfront Condo w/ Pool Access in Hilton Head!

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

Coastal Calm Couples Paradise + KING Bed+ Bikes-#131
South End
10.0 out of 10, Exceptional, (16 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$564
includes taxes & fees
25 Aug - 26 Aug
Coastal Calm Couples Paradise + KING Bed+ Bikes-#131

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

Beautiful Couples Retreat Oceanview w/new bikes&Chairs
South End
9.8 out of 10, Exceptional, (130 reviews)
"Very relaxing views. "
United States
ashley l.
The price is NZ$455
includes taxes & fees
1 Sept - 2 Sept
Beautiful Couples Retreat Oceanview w/new bikes&Chairs

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

Gone Coastal! 2 from oceanfront! Central air!
South End
9.8 out of 10, Exceptional, (28 reviews)
"Loved the location!"
United States
Allison O.
The price is NZ$445
includes taxes & fees
31 Aug - 1 Sept
Gone Coastal! 2 from oceanfront! Central air!

18. Just Beachy! Absolute top notch design, Oceanviews

Just Beachy! Absolute top notch design, Oceanviews
South End
9.8 out of 10, Exceptional, (44 reviews)
"This was our first time to the Hilton Head area and we really enjoyed our stay. We would definitely stay here again!"
United States
Ashley B.
The price is NZ$439
includes taxes & fees
25 Aug - 26 Aug
Just Beachy! Absolute top notch design, Oceanviews

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

Shore Beats Work!-Stunning view 3 from oceanfront new bikes Incl.
South End
9.4 out of 10, Exceptional, (61 reviews)
"Clean and in a great location. Host communicated quickly when needed."
United States
Rena
Shore Beats Work!-Stunning view 3 from oceanfront new bikes Incl.

20. OceanEscape – Steps to the Beach

OceanEscape – Steps to the Beach
South End
9.8 out of 10, Exceptional, (79 reviews)
"Great location!"
United States
Alycia R.
The price is NZ$443
includes taxes & fees
30 Aug - 31 Aug
OceanEscape – Steps to the Beach
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

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$528 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. 

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.