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

Seabatical-Beautiful ocean view! w/new bikes & Chairs
South End
10.0 out of 10, Exceptional, (92 reviews)
"The room was perfect myself and my cousin. We loved how the room was right on the beach. We also enjoyed the bikes, beach chairs, toys and how close it was to Coligny beach park. Would definitely stay here again."
United States
Raven
Seabatical-Beautiful ocean view! w/new bikes & Chairs

2. Castaways King Villa on Beach, Free Bikes!

Castaways King Villa on Beach, Free Bikes!
South End
10.0 out of 10, Exceptional, (119 reviews)
"Place was on the 1st floor and very convenient location. Pool is a little small but clean. Gate to get in was a little to be desired because it was hard for 2 cars to pass at the same time. Place was clean and host was very easy to deal with and answered any questions for me ASAP. Would stay again. Great for couples."
United States
Kathleen
The price is NZ$470
includes taxes & fees
16 Sept - 17 Sept
Castaways King Villa on Beach, Free Bikes!

3. Luxury Penthouse near Beach, Tiki Hut, Coligny

Luxury Penthouse near Beach, Tiki Hut, Coligny
South End
10.0 out of 10, Exceptional, (119 reviews)
"Had a great stay. Definitely recommend."
United States
Thomas K.
The price is NZ$994
includes taxes & fees
27 Sept - 28 Sept
Luxury Penthouse near Beach, Tiki Hut, Coligny

4. 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$423
includes taxes & fees
16 Sept - 17 Sept
Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view

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

SeaClusion-Oceanview, Mini split AC, Beach Chairs
South End
9.8 out of 10, Exceptional, (81 reviews)
"Great area location property and beach to enjoy a small getaway"
United States
Nicholas P.
SeaClusion-Oceanview, Mini split AC, Beach Chairs

6. 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$667
includes taxes & fees
16 Sept - 17 Sept
Beachfront Condo w/ Pool Access in Hilton Head!

7. 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$555
includes taxes & fees
17 Sept - 18 Sept
Serene Tides & Relaxing Sunny Days Retreat-Coligny+ Bikes-#233!

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

Beachfront Condo w/ Pool Access in Hilton Head!
South End
9.2 out of 10, Wonderful, (94 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!

9. 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)
"Perfect location, check in was very easy. The condo was clean and everything exactly as it was described. Would definitely stay here again."
United States
Shane W.
The price is NZ$526
includes taxes & fees
20 Sept - 21 Sept
Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

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.
Just Beachy! Absolute top notch design, Oceanviews

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

Coastal Calm Couples Paradise + KING Bed+ Bikes-#131
South End
10.0 out of 10, Exceptional, (19 reviews)
"Within steps of the ocean, great location to bike and walking trail, close to shops and dining. "
United States
Dee W.
Coastal Calm Couples Paradise + KING Bed+ Bikes-#131

12. Coastal Getaway: Oceanview Condo in Hilton Head

Coastal Getaway: Oceanview Condo in Hilton Head
South End
9.6 out of 10, Exceptional, (23 reviews)
"Great location, very comfortable, and I felt safe "
United States
Wendy C.
Coastal Getaway: Oceanview Condo in Hilton Head

13. Coastal Nest - Oceanviews! Near Coligny

Coastal Nest - Oceanviews! Near Coligny
South End
9.2 out of 10, Wonderful, (20 reviews)
"We loved how close it is to the beach! "
United States
Andrea R.
Coastal Nest - Oceanviews! Near Coligny

14. Beauty at the Beach! Oceanview King bed free bikes

Beauty at the Beach! Oceanview King bed free bikes
South End
9.8 out of 10, Exceptional, (61 reviews)
"Excellent stay - the room was clean, the host was easy to communicate with and provided most everything we needed. It had a nice beach view and provided beach chairs and bikes. We would stay again."
United States
Debra B.
Beauty at the Beach! Oceanview King bed free bikes

15. Stunning Oceanview Luxury Remodel, Bikes Included!

Stunning Oceanview Luxury Remodel, Bikes Included!
South End
10.0 out of 10, Exceptional, (163 reviews)
"Thoroughly enjoyed our stay. Condo provided everything we needed plus the location being so close to the beach was just great."
United States
Bob F.
Stunning Oceanview Luxury Remodel, Bikes Included!

16. Steps to the beach! Newly Remodeled! New furniture. Avail

Steps to the beach! Newly Remodeled! New furniture. Avail
Mid Island
9.6 out of 10, Exceptional, (114 reviews)
"Short, but enjoyable stay. Would stay again!"
United States
Dora D.
The price is NZ$587
includes taxes & fees
20 Sept - 21 Sept
Steps to the beach! Newly Remodeled! New furniture. Avail

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

Beautiful Couples Retreat Oceanview w/new bikes&Chairs
South End
9.8 out of 10, Exceptional, (131 reviews)
"Great location, Kendall is very responsive and thoughtful, place was clean and beach equipment was nice."
United States
Julee S.
Beautiful Couples Retreat Oceanview w/new bikes&Chairs

18. 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, (63 reviews)
"The room has a good view of the ocean and the hosts were great!"
United States
Matt W.
The price is NZ$447
includes taxes & fees
16 Sept - 17 Sept
Shore Beats Work!-Stunning view 3 from oceanfront new bikes Incl.

19. Coral Paradise, Ocean View, Couple's Seaside Retreat, Pool, Walk to Shops Dining

Coral Paradise, Ocean View, Couple's Seaside Retreat, Pool, Walk to Shops Dining
South End
10.0 out of 10, Exceptional, (12 reviews)
"The villa is perfectly located within walking distance to Coligny Plaza and the provided wagon to take to the beach was wonderful! Will definitely stay again when I return to HHI!"
United States
Candice L.
Coral Paradise, Ocean View, Couple's Seaside Retreat, Pool, Walk to Shops Dining

20. Direct Oceanfront: Million Dollar Sunrise Views & Steps to Coligny

Direct Oceanfront: Million Dollar Sunrise Views & Steps to Coligny
South End
9.2 out of 10, Wonderful, (321 reviews)
"Wonderful view and convenient location. He condo was very clean. Will look to stay here again."
United States
Phillip C.
Direct Oceanfront: Million Dollar Sunrise Views & Steps to Coligny
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

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.

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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 scenic seaside 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?

Stunning Ocean View Vacation House with Private Pool, 1 Min From Beach!: This highly rated holiday home rental in Hilton Head Island offers a balcony, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind. Other favourite homes for rent in Hilton Head Island are Custom Built GORGEOUS 5 Bedroom Sea Pines Home w/ Private Pool + Screen Porch and Private Pool 4 Bedroom 2 Bathroom South Forest Beach Home! Steps to the beach!!.

How many holiday rentals are there in Hilton Head Island?

With 984 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. Marine Corps Recruit Depot Parris Island and River Street 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.