A coastal town with a lighthouse, marina, and golf course.

Hilton Head Island Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Hilton Head Island holiday rentals

On the beach

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, (172 reviews)
"Amazing place to vacation. Loved the view. Beach paradise extremely clean, quiet, easy beach access."
United States
Linda P.
The price is NZ$454
includes taxes & fees
17 Aug - 18 Aug
Flip Flop Paradise-Steps to the Sand! Free Bikes
On the beach

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$447
includes taxes & fees
16 Aug - 17 Aug
Feelin Tip'Sea-Oceanview Retreat Steps to Beach
Terrace/patio

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$539
includes taxes & fees
7 Sept - 8 Sept
Marriott's Harbour Point and Sunset Pointe at Shelter Cove
On the beach

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$447
includes taxes & fees
16 Aug - 17 Aug
Seas the Day! Beach & Sun, with Bikes & Chairs
Apartment (1 Bedroom) | Front of property

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$669
includes taxes & fees
26 Aug - 27 Aug
Beachfront Condo w/ Pool Access in Hilton Head!
Property grounds

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
The price is NZ$455
includes taxes & fees
19 Aug - 20 Aug
Beach Daze-Gorgeous new shower! Bikes Included
Terrace/patio

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, (154 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$437
includes taxes & fees
1 Sept - 2 Sept
Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view
On the beach, sun-loungers, beach towels

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$537
includes taxes & fees
27 Aug - 28 Aug
STUNNING ocean view! Brand new listing
On the beach

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.
The price is NZ$528
includes taxes & fees
15 Aug - 16 Aug
Good Times and Tan Lines!-Central air, free bikes!
On the beach

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.
The price is NZ$449
includes taxes & fees
30 Aug - 31 Aug
Seabatical-Beautiful ocean view! w/new bikes & Chairs
On the beach

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$446
includes taxes & fees
16 Aug - 17 Aug
Coastal Nest - Oceanviews! Near Coligny
Property grounds

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, (177 reviews)
"Weather wasn’t good but the accommodations were good."
United States
Michael B.
The price is NZ$526
includes taxes & fees
12 Sept - 13 Sept
Crashin' Waves-Oceanview w/new bikes, Chairs& King Bed
Indoor pool, 5 outdoor pools, pool umbrellas, pool loungers

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$952
includes taxes & fees
8 Sept - 9 Sept
Marriott's Grande Ocean
Interior

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$449
includes taxes & fees
2 Sept - 3 Sept
SeaClusion-Oceanview, Mini split AC, Beach Chairs
On the beach

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$458
includes taxes & fees
30 Aug - 31 Aug
SerenityByTheSea-Couples Retreat-King,Bikes,Chairs
Villa (2 Bedrooms) | Interior

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$651
includes taxes & fees
16 Aug - 17 Aug
Walk to Beach: Hilton Head Condo w/ Pool Access
TV

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$678
includes taxes & fees
26 Aug - 27 Aug
Beachfront Condo w/ Pool Access in Hilton Head!
On the beach

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.
The price is NZ$451
includes taxes & fees
26 Aug - 27 Aug
Gone Coastal! 2 from oceanfront! Central air!
Property grounds

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
Smart TV

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

Palmera Inn and Suites

Palmera Inn and Suites

10/10 Excellent
"Room and breakfast area were clean and the staff is nice."
Deanna 1-night trip
Posted 13 hours ago
Palmera Inn and Suites

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 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.