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

Seas the Day! Beach & Sun, with Bikes & Chairs
South End
9.8 out of 10, Exceptional, (38 reviews)
"Great Stay."
United States
Robert
The price is NZ$463
includes taxes & fees
29 Sept - 30 Sept
Seas the Day! Beach & Sun, with Bikes & Chairs

2. 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

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

SeaClusion-Oceanview, Mini split AC, Beach Chairs
South End
9.8 out of 10, Exceptional, (82 reviews)
"Great area location property and beach to enjoy a small getaway"
United States
Nicholas P.
SeaClusion-Oceanview, Mini split AC, Beach Chairs

4. 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
Beach Daze-Gorgeous new shower! Bikes Included

5. STUNNING ocean view! Brand new listing

STUNNING ocean view! Brand new listing
South End
9.8 out of 10, Exceptional, (20 reviews)
"Absolutely loved our stay would recommend"
United States
xiaoming w.
STUNNING ocean view! Brand new listing

6. 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, (188 reviews)
"Loved the bikes and location to everything. We were comfortable and had all we needed for the beach too."
United States
Margaret
The price is NZ$542
includes taxes & fees
4 Oct - 5 Oct
Crashin' Waves-Oceanview w/new bikes, Chairs& King Bed

7. Coastal Nest - Oceanviews! Near Coligny

Coastal Nest - Oceanviews! Near Coligny
South End
9.4 out of 10, Exceptional, (22 reviews)
"We loved how close it is to the beach! "
United States
Andrea R.
The price is NZ$449
includes taxes & fees
6 Oct - 7 Oct
Coastal Nest - Oceanviews! Near Coligny

8. SeaRenity! Beautiful Reno! King bed! w/Bikes

SeaRenity! Beautiful Reno! King bed! w/Bikes
South End
9.6 out of 10, Exceptional, (133 reviews)
"Great stay!"
United States
Sean L.
The price is NZ$463
includes taxes & fees
29 Sept - 30 Sept
SeaRenity! Beautiful Reno! King bed! w/Bikes

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, (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.
The price is NZ$693
includes taxes & fees
21 Oct - 22 Oct
Beachfront Condo w/ Pool Access in Hilton Head!

10. Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116

Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116
Mid Island
9.6 out of 10, Exceptional, (116 reviews)
"Short, but enjoyable stay. Would stay again!"
United States
Dora D.
The price is NZ$605
includes taxes & fees
12 Oct - 13 Oct
Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116

11. 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, (158 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$522
includes taxes & fees
19 Oct - 20 Oct
Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view

12. 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$596
includes taxes & fees
4 Oct - 5 Oct
Marriott's Grande Ocean

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)
"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$554
includes taxes & fees
11 Oct - 12 Oct
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
8.0 out of 10, Very good, (3 reviews)
"The security guard was friendly. The condo was clean. I am not sure if all of these were from the host or left behind but there was a coffee maker, spice rack (which I’ve never seen in a condo before), dishwasher, plenty of pots and pans, not a lot of utensils for cooking, a hair dryer, small tin of coffee creamer, pool towel (clean), extra blankets (clean), a single trash bag for the kitchen, paper towels, kitchen towel, chairs and beach things on the deck. It was on the beach just have to walk...
United States
Manuel
The price is NZ$681
includes taxes & fees
21 Oct - 22 Oct
Beachfront Condo w/ Pool Access in Hilton Head!

15. 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, (84 reviews)
"Nice quiet area...could see the ocean from the balcony!! Clean and close to various shops and resturant s..will stay again!!"
United States
Suzanne O.
Good Times and Tan Lines!-Central air, free bikes!

16. Coastal Getaway: Oceanview Condo in Hilton Head

Coastal Getaway: Oceanview Condo in Hilton Head
South End
9.6 out of 10, Exceptional, (24 reviews)
"Great location, very comfortable, and I felt safe "
United States
Wendy C.
The price is NZ$461
includes taxes & fees
30 Sept - 1 Oct
Coastal Getaway: Oceanview Condo in Hilton Head

17. Just Beachy! Absolute top notch design, Oceanviews

Just Beachy! Absolute top notch design, Oceanviews
South End
9.8 out of 10, Exceptional, (46 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$463
includes taxes & fees
30 Sept - 1 Oct
Just Beachy! Absolute top notch design, Oceanviews

18. OceanEscape – Steps to the Beach

OceanEscape – Steps to the Beach
South End
9.8 out of 10, Exceptional, (84 reviews)
"Great location!"
United States
Alycia R.
OceanEscape – Steps to the Beach

19. 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.
Serene Tides & Relaxing Sunny Days Retreat-Coligny+ Bikes-#233!

20. 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
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?

New Four BR Luxury Vacation Home on Hilton Head: This highly rated holiday home rental in Hilton Head Island has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a microwave, so that you can cook with friends or family. Other favourite homes for rent in Hilton Head Island are Palmetto Dunes, pool, hot tub, walk to beach, dog friendly, bikes, sleeps 15 and Stunning Ocean View Vacation House with Private Pool, 1 Min From Beach!.

How many holiday rentals are there in Hilton Head Island?

With 1003 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.