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. 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

2. Castaways King Villa on Beach, Free Bikes!

Castaways King Villa on Beach, Free Bikes!
South End
10.0 out of 10, Exceptional, (112 reviews)
"The property was amazing. The pool was perfect. The beach was only a few steps away and everything was great. Beautiful view of the ocean from our balcony was a plus every morning."
United States
Stephen
The price is NZ$467
includes taxes & fees
15 Aug - 16 Aug
Castaways King Villa on Beach, Free Bikes!

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

Feelin Tip'Sea-Oceanview Retreat Steps to Beach
South End
9.8 out of 10, Exceptional, (35 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$450
includes taxes & fees
16 Aug - 17 Aug
Feelin Tip'Sea-Oceanview Retreat Steps to Beach

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, (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$439
includes taxes & fees
2 Sept - 3 Sept
Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view

5. Beachy Keen Seaside Villa Near Coligny W/Bikes!

Beachy Keen Seaside Villa Near Coligny W/Bikes!
South End
9.8 out of 10, Exceptional, (90 reviews)
"Great stay!"
United States
Katleen M.
The price is NZ$438
includes taxes & fees
3 Sept - 4 Sept
Beachy Keen Seaside Villa Near Coligny W/Bikes!

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

Seabatical-Beautiful ocean view! w/new bikes & Chairs
South End
10.0 out of 10, Exceptional, (89 reviews)
"We are enjoyed stay for my kids golf tournament. "
United States
Yongni G.
Seabatical-Beautiful ocean view! w/new bikes & Chairs

7. Marriott's Barony Beach Club

Marriott's Barony Beach Club
3.5 star property
Mid Island
9.4 out of 10, Exceptional, (252 reviews)
"I wish we could have stayed longer. Love that we were able to do laundry, although I do wish the water slide was open. My grandchildren would have loved it. We got a villa/suite facing the water park/pool area so my elderly mother could take pictures. 4 generations, what a blessing."
United States
Anneka
The price is NZ$778
includes taxes & fees
30 Aug - 31 Aug
Marriott's Barony Beach Club

8. Gone Coastal! 2 from oceanfront! Central air!

Gone Coastal! 2 from oceanfront! Central air!
South End
9.8 out of 10, Exceptional, (23 reviews)
"Loved the location!"
United States
Allison O.
Gone Coastal! 2 from oceanfront! Central air!

9. 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$647
includes taxes & fees
12 Aug - 13 Aug
Walk to Beach: Hilton Head Condo w/ Pool Access

10. 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, (170 reviews)
"Clean and close to the beach! "
United States
Youn Jin L.
Flip Flop Paradise-Steps to the Sand! Free Bikes

11. Elegance at the beach -Ocean View Villa, Gorgeous!

Elegance at the beach -Ocean View Villa, Gorgeous!
South End
10.0 out of 10, Exceptional, (117 reviews)
"We loved our stay! The place was exactly as described. The location and beach access was perfect. Quiet, peaceful, comfortable-just what we needed. Loved that we could walk to restaurants in the mornings and evenings!Kendall was great with communication!Would definitely stay again and hope to in the future"
United States
Jacki M.
Elegance at the beach -Ocean View Villa, Gorgeous!

12. 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, (95 reviews)
"Great condo, location, beach. "
United States
Steven S.
The price is NZ$452
includes taxes & fees
20 Aug - 21 Aug
SeaGem-Oceanview! Steps to ocean Many Upgrades New Reno

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, (129 reviews)
"Very relaxing views. "
United States
ashley l.
Beautiful Couples Retreat Oceanview w/new bikes&Chairs

14. Coastal Getaway: Oceanview Condo in Hilton Head

Coastal Getaway: Oceanview Condo in Hilton Head
South End
9.6 out of 10, Exceptional, (21 reviews)
"Great location, very comfortable, and I felt safe "
United States
Wendy C.
The price is NZ$450
includes taxes & fees
15 Aug - 16 Aug
Coastal Getaway: Oceanview Condo in Hilton Head

15. 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, (175 reviews)
"Weather wasn’t good but the accommodations were good."
United States
Michael B.
Crashin' Waves-Oceanview w/new bikes, Chairs& King Bed

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)
"Nice view from balcony, property was very clean. "
United States
Arnas C.
The price is NZ$543
includes taxes & fees
10 Aug - 11 Aug
Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

17. 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, (154 reviews)
"Very nice place to stay "
United States
Alejandro
The price is NZ$650
includes taxes & fees
26 Aug - 27 Aug
Marriott's Harbour Point and Sunset Pointe at Shelter Cove

18. 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, (113 reviews)
"Great location, great host, perfect space! Everything was super close and convenient. Would highly recommend"
United States
Jannyn
The price is NZ$643
includes taxes & fees
15 Aug - 16 Aug
Steps to the beach! Newly Remodeled! New furniture. Avail

19. 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
Beachfront Condo w/ Pool Access in Hilton Head!

20. SerenityByTheSea-Couples Retreat-King,Bikes,Chairs

SerenityByTheSea-Couples Retreat-King,Bikes,Chairs
South End
10.0 out of 10, Exceptional, (175 reviews)
"Wonderful time close to everything easy walk to the beach"
United States
charles g.
The price is NZ$512
includes taxes & fees
20 Aug - 21 Aug
SerenityByTheSea-Couples Retreat-King,Bikes,Chairs
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 Arts Center of Coastal Carolina, 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?

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. Other favourite homes for rent in Hilton Head Island are Sunset Canopy at Harbourtown and Backyard pickleball. Private Pool. Large family home! Custom Outdoor kitchen..

How many holiday rentals are there in Hilton Head Island?

With 1010 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 Coligny Beach and Sea Pines Forest Preserve 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.