Hilton Head Island Holiday Rentals from €125: Search Short-Term Rentals

Q: 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 Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380 .

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Hilton Head Island holiday rentals

A wooden boardwalk leading to a beach with a bicycle parked on it.

1. Marriott's Monarch at Sea Pines

Sea Pines

Sharon

includes taxes & fees

4 Nov - 5 Nov

A spacious living area with a high ceiling, large windows, and a central seating arrangement.

2. Marriott's Heritage Club

Sea Pines

Christine

includes taxes & fees

3 Nov - 4 Nov

A modern living room with a staircase, a bar area, and a couch.

3. Luxury Penthouse near Beach, Tiki Hut, Coligny

South End

Thomas K.

includes taxes & fees

12 Oct - 13 Oct

A deck with sun loungers overlooking a natural landscape.

4. Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

South End

Patsy

includes taxes & fees

12 Oct - 13 Oct

A modern living room with a glass coffee table, a sofa, a white nightstand, and a large mirror.

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

South End

Gary B.

includes taxes & fees

12 Oct - 13 Oct

A living room with a television, a wicker chair, a glass coffee table, and a view of the ocean through a sliding glass door.

6. Palm Breezy Living-Coligny+Bikes included-#228

South End

Mayra S.

includes taxes & fees

12 Oct - 13 Oct

A beach with a calm sea and a clear sky.

7. Steps to Beach-hilton Head Condo-pet Friendly

Mid Island

includes taxes & fees

22 Oct - 23 Oct

A courtyard with a central fountain, surrounded by palm trees and a large tree in the background.

8. Coligny Beach, Pools, & Shops- Few Steps Away

South End

Cheryl M.

A beachside resort with a swimming pool, lounge chairs, and a small building, likely a lifeguard station.

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

Mid Island

Dora D.

includes taxes & fees

25 Oct - 26 Oct

A sandy beach with tall grasses in the foreground and a clear blue sky.

Amanda F.

A waterfront restaurant with outdoor seating and a view of the water.

17. Disney's Hilton Head Island Resort

Mid Island

Melissa

A balcony with a view of the ocean, palm trees, and a building with large windows.

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

South End

LeeAnn E.

A covered outdoor area with a view of the ocean, palm trees, and a grassy landscape.

19. Direct Ocean Front First Floor 1BR/1Bath Condo

South End

Betty H.

includes taxes & fees

17 Oct - 18 Oct

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

South End

"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...

Manuel

includes taxes & fees

12 Oct - 13 Oct

View all properties

Find holiday rentals that suit your style

Villas

Private holiday homes

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Hilton Head Island Hotel Reviews

Palmera Inn and Suites

10/10 Excellent

"This inn is very clean with a friendly staff in a convenient location."

Hilton Grand Vacations Club Ocean Oak Resort Hilton Head

8/10 Good

"We were very impressed by our 2 bedroom suite - definitely nicer than the Marriott’s Grande Ocean we stayed at last year, just down the street. Only 2 complaints were that rooms aren’t cleaned on Saturdays. Not a big deal but we just had a ton of trash piled up. And then when they did come, they didn’t make the beds. I don’t think I’ve ever stayed at a hotel where they came and cleaned but didn’t make the beds. 😅 Small complaints - we really enjoyed our stay and the pool and hot tub was very nice."

Doubletree by Hilton Hilton Head Island

10/10 Excellent

"Good morning! My wife and I truly enjoyed our stay at your facility, upon arriving at the Hotel's front desk we were greeted very kindly. Once assigned to our room the area was well kept, the bathroom was extremely clean. Both heater and AC were functional, along with the flat screen television. We were visiting to attend annual Fish & Grit Festival; the Hotel was centrally located just three blocks from the Low Country Park. Once again, our stay was very pleasant."

Find out more about Hilton Head Island

Everything you need to know about Hilton Head Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hilton Head Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hilton Head Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hilton Head Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hilton Head Island. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hilton Head Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hilton Head Island holiday rentals we have selected for you start as low as €125 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hilton Head Island rentals

At Expedia, we put the best Hilton Head Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Hilton Head Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hilton Head Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hilton Head Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 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 Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380.

How many holiday rentals are there in Hilton Head Island?

With 986 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.

Holiday Rentals in Hilton Head Island

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Hilton Head Island holiday rentals

1. Marriott's Monarch at Sea Pines

2. Marriott's Heritage Club

3. Luxury Penthouse near Beach, Tiki Hut, Coligny

4. Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

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

6. Palm Breezy Living-Coligny+Bikes included-#228

7. Steps to Beach-hilton Head Condo-pet Friendly

8. Coligny Beach, Pools, & Shops- Few Steps Away

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

10. Oceanfront Hilton Head Island Condo w/ Pool!

11. Marriott's Grande Ocean

12. Marriott's Harbour Club

13. Flip Flop Paradise-Steps to the Sand! Free Bikes

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

15. Ocean View Villa with Amazing Resort Amenities -- just steps from the beach!!!

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

17. Disney's Hilton Head Island Resort

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

19. Direct Ocean Front First Floor 1BR/1Bath Condo

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

Find holiday rentals that suit your style

Top Hilton Head Island Hotel Reviews

Palmera Inn and Suites

Find out more about Hilton Head Island

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app