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. 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$652
includes taxes & fees
22 Sept - 23 Sept
Beachfront Condo w/ Pool Access in Hilton Head!

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

SeaClusion-Oceanview, Mini split AC, Beach Chairs
South End
9.8 out of 10, Exceptional, (78 reviews)
"Very conveniently located and reasonably priced. Great for a weekend couples’ getaway."
United States
Kevin W.
The price is NZ$447
includes taxes & fees
2 Sept - 3 Sept
SeaClusion-Oceanview, Mini split AC, Beach Chairs

3. 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$413
includes taxes & fees
2 Sept - 3 Sept
Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view

4. 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$534
includes taxes & fees
7 Sept - 8 Sept
Marriott's Harbour Point and Sunset Pointe at Shelter Cove

5. SunnyDaze-Brand new reno- King bed, Free bikes!

SunnyDaze-Brand new reno- King bed, Free bikes!
South End
9.6 out of 10, Exceptional, (107 reviews)
"We had a wonderful stay. Super helpful host, clean room, and a nice location! We'll be back!"
United States
andrew b.
SunnyDaze-Brand new reno- King bed, Free bikes!

6. Beach Daze-Gorgeous new shower! Bikes Included

Beach Daze-Gorgeous new shower! Bikes Included
South End
9.8 out of 10, Exceptional, (31 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$459
includes taxes & fees
7 Sept - 8 Sept
Beach Daze-Gorgeous new shower! Bikes Included

7. 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.
Coastal Nest - Oceanviews! Near Coligny

8. 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

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

Seas the Day! Beach & Sun, with Bikes & Chairs
South End
9.6 out of 10, Exceptional, (35 reviews)
"Great Stay."
United States
Robert
Seas the Day! Beach & Sun, with Bikes & Chairs

10. 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$442
includes taxes & fees
2 Sept - 3 Sept
Just Beachy! Absolute top notch design, Oceanviews

11. 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

12. STUNNING ocean view! Brand new listing

STUNNING ocean view! Brand new listing
South End
10.0 out of 10, Exceptional, (17 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.
STUNNING ocean view! Brand new listing

13. Coastal Getaway: Oceanview Condo in Hilton Head

Coastal Getaway: Oceanview Condo in Hilton Head
South End
9.6 out of 10, Exceptional, (22 reviews)
"Great location, very comfortable, and I felt safe "
United States
Wendy C.
Coastal Getaway: Oceanview Condo in Hilton Head

14. 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$943
includes taxes & fees
7 Sept - 8 Sept
Marriott's Grande Ocean

15. Beachy chic, steps from the beach!

Beachy chic, steps from the beach!
Mid Island
9.4 out of 10, Exceptional, (69 reviews)
"Great location, short walk to beach and pool. "
United States
Amy H.
The price is NZ$553
includes taxes & fees
2 Sept - 3 Sept
Beachy chic, steps from the beach!

16. 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$507
includes taxes & fees
8 Sept - 9 Sept
Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

17. Beach Happy!-Nice ocean view Hilton Head Villa

Beach Happy!-Nice ocean view Hilton Head Villa
South End
9.4 out of 10, Exceptional, (39 reviews)
"Would love to stay here again! Great location and great host!"
United States
Diana J.
The price is NZ$460
includes taxes & fees
2 Sept - 3 Sept
Beach Happy!-Nice ocean view Hilton Head Villa

18. 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, (182 reviews)
"For a couple looking to fly in to HHI and have a low stress, beach front space, this property is a great choice. The access to bikes, pool, beach chairs and beach towels meant we could pack light and enjoy from the first moment we arrived. Walks on the beach and delicious meals at Nectar and Tio’s were the highlights!"
United States
Erica F.
The price is NZ$463
includes taxes & fees
3 Sept - 4 Sept
Crashin' Waves-Oceanview w/new bikes, Chairs& King Bed

19. 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$662
includes taxes & fees
4 Sept - 5 Sept
Beachfront Condo w/ Pool Access in Hilton Head!

20. Serene Tides & Relaxing Sunny Days Retreat-Coligny+ Bikes-#233!

Serene Tides & Relaxing Sunny Days Retreat-Coligny+ Bikes-#233!
South End
9.8 out of 10, Exceptional, (161 reviews)
"The hosts were very accommodating, along with providing great insights into great places to visit and eat at on the island!"
United States
John P.
The price is NZ$683
includes taxes & fees
4 Sept - 5 Sept
Serene Tides & Relaxing Sunny Days Retreat-Coligny+ Bikes-#233!
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$534 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 1026 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.