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. 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.
The price is NZ$468
includes taxes & fees
23 Sept - 24 Sept
SeaClusion-Oceanview, Mini split AC, Beach Chairs

2. Feelin Tip'Sea-Oceanview Retreat Steps to Beach

Feelin Tip'Sea-Oceanview Retreat Steps to Beach
South End
9.6 out of 10, Exceptional, (40 reviews)
"Room was as shown in pictures. Clean, steps from the beach, walking distance to Coligny Park & local shops & restaurants. Had wonderful weather during week of September 12-17. Felt safe with gated entrance & parking."
United States
Robin
Feelin Tip'Sea-Oceanview Retreat Steps to Beach

3. 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

4. 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$945
includes taxes & fees
4 Oct - 5 Oct
Luxury Penthouse near Beach, Tiki Hut, Coligny

5. 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
29 Sept - 30 Sept
Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

6. STUNNING ocean view! Brand new listing

STUNNING ocean view! Brand new listing
South End
9.8 out of 10, Exceptional, (19 reviews)
"Absolutely loved our stay would recommend"
United States
xiaoming w.
STUNNING ocean view! Brand new listing

7. 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

8. 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, (156 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$473
includes taxes & fees
30 Sept - 1 Oct
Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view

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

SunnyDaze-Brand new reno- King bed, Free bikes!
South End
9.6 out of 10, Exceptional, (108 reviews)
"Great place to stay!"
United States
Jake H.
SunnyDaze-Brand new reno- King bed, Free bikes!

10. Coastal Nest - Oceanviews! Near Coligny

Coastal Nest - Oceanviews! Near Coligny
South End
9.4 out of 10, Exceptional, (21 reviews)
"We loved how close it is to the beach! "
United States
Andrea R.
Coastal Nest - Oceanviews! Near Coligny

11. 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$625
includes taxes & fees
24 Sept - 25 Sept
Marriott's Grande Ocean

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. 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.
The price is NZ$463
includes taxes & fees
24 Sept - 25 Sept
Beautiful Couples Retreat Oceanview w/new bikes&Chairs

14. 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.
Shore Beats Work!-Stunning view 3 from oceanfront new bikes Incl.

15. Just Beachy! Absolute top notch design, Oceanviews

Just Beachy! Absolute top notch design, Oceanviews
South End
9.8 out of 10, Exceptional, (45 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

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, (115 reviews)
"Short, but enjoyable stay. Would stay again!"
United States
Dora D.
The price is NZ$599
includes taxes & fees
22 Sept - 23 Sept
Steps to the beach! Newly Remodeled! New furniture. Avail

17. 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, (81 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.
The price is NZ$479
includes taxes & fees
22 Sept - 23 Sept
Good Times and Tan Lines!-Central air, free bikes!

18. 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

19. Sunset Dunes Direct Beach Access

Sunset Dunes Direct Beach Access
South End
9.8 out of 10, Exceptional, (139 reviews)
"Great place to stay. Will definitely stay here again"
United States
Celeste G.
Sunset Dunes Direct Beach Access

20. Beautiful Spacious w/Indoor Outdoor Pool, Hot Tub, Tennis, Pickle Ball & Beach !

Beautiful Spacious w/Indoor Outdoor Pool, Hot Tub, Tennis, Pickle Ball & Beach !
South End
10.0 out of 10, Exceptional, (18 reviews)
"The place was PERFECT! The set up was incredible and it was easy to access and close to everything are wanted to do. We really enjoyed our stay and will not hesitate to come back here."
United States
Kathleen P.
The price is NZ$642
includes taxes & fees
26 Sept - 27 Sept
Beautiful Spacious w/Indoor Outdoor Pool, Hot Tub, Tennis, Pickle Ball & 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.
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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 1012 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.