A coastal town with a lighthouse, marina, and golf course.

Hilton Head Island Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Hilton Head Island holiday rentals

A covered outdoor area with a pool, lounge chairs, and a sofa.

1. Marriott's SurfWatch

Marriott's SurfWatch
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (202 reviews)
"Great resort, great room "
United States
Crista
The price is NZ$848
includes taxes & fees
1 Sept - 2 Sept
Marriott's SurfWatch
A hotel entrance with a grand staircase, a covered walkway, and a brick-paved area.

2. Marriott's Harbour Club

Marriott's Harbour Club
3.5 star property
Sea Pines
9.0 out of 10, Wonderful, (63 reviews)
"Clean and spacious. Very convenient location. "
United States
CLAUDIA
The price is NZ$516
includes taxes & fees
2 Sept - 3 Sept
Marriott's Harbour Club
A waterfront restaurant with outdoor seating and a view of the water.

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. Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access
2.0 star property
South End
The price is NZ$1,556
includes taxes & fees
4 Sept - 5 Sept
Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access
A beach with a row of blue umbrellas and a path leading to the water.

5. Ocean Palms Villas at Port Royal Resort

Ocean Palms Villas at Port Royal Resort
3.5 star property
Mid Island
8.6 out of 10, Excellent, (98 reviews)
"It was perfect for our needs. Check-in was super easy!"
United States
Melanie
The price is NZ$714
includes taxes & fees
9 Sept - 10 Sept
Ocean Palms Villas at Port Royal Resort
A historic building with a covered porch and a brick pathway.

6. Montage Palmetto Bluff Residences

Montage Palmetto Bluff Residences
5.0 star property
Palmetto Bluff
10.0 out of 10, Exceptional, (2 reviews)
"Very family friendly. Parking was a problem Check in was not one minute early. House was beautiful and very clean. Pool was wonderful Prices were high but we knew that ahead of time"
United States
john j
The price is NZ$2,926
includes taxes & fees
28 Sept - 29 Sept
Montage Palmetto Bluff Residences
A modern kitchen with granite countertops, a stainless steel sink, and wooden cabinets.

7. Palmetto Dunes Golf Getaway: Pool + Beach Access!

Palmetto Dunes Golf Getaway: Pool + Beach Access!
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (1 review)
"Communication with owner is excellent and villa is located in great location "
United States
minoshka
The price is NZ$693
includes taxes & fees
8 Sept - 9 Sept
Palmetto Dunes Golf Getaway: Pool + Beach Access!
An indoor swimming pool with clear glass ceilings, multiple lounge chairs, and a view of the outdoors.

8. Marriott's Barony Beach Club

Marriott's Barony Beach Club
3.5 star property
Mid Island
9.4 out of 10, Exceptional, (252 reviews)
"Family orientated hotel with great pools, walk on beach access, wonderful BBQ options for self catering. Rooms are large and family orientated. Fab stay! "
Australia
Pauline
The price is NZ$911
includes taxes & fees
1 Sept - 2 Sept
Marriott's Barony Beach Club
A spacious living area with a high ceiling, large windows, and a central seating arrangement.

9. Marriott's Heritage Club

Marriott's Heritage Club
3.5 star property
Sea Pines
9.4 out of 10, Exceptional, (71 reviews)
"Great Villa! Very roomy and excellent location close to everything!"
United States
Christine
The price is NZ$575
includes taxes & fees
8 Sept - 9 Sept
Marriott's Heritage Club

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

Steps to Beach-hilton Head Condo-pet Friendly
2.0 star property
Mid Island
The price is NZ$881
includes taxes & fees
31 Aug - 1 Sept
Steps to Beach-hilton Head Condo-pet Friendly
A wooden boardwalk leading to a gate, surrounded by lush greenery and palm trees.

11. Walk to Bars & Shops: Resort Condo in Hilton Head!

Walk to Bars & Shops: Resort Condo in Hilton Head!
3.5 star property
South End
The price is NZ$616
includes taxes & fees
13 Sept - 14 Sept
Walk to Bars & Shops: Resort Condo in Hilton Head!
A wooden boardwalk leading to a beach with a bicycle parked on it.

12. Marriott's Monarch at Sea Pines

Marriott's Monarch at Sea Pines
3.0 star property
Sea Pines
9.2 out of 10, Wonderful, (132 reviews)
"Loved this property "
United States
Sharon
The price is NZ$886
includes taxes & fees
8 Sept - 9 Sept
Marriott's Monarch at Sea Pines
An aerial view of a resort with multiple buildings, a central swimming pool, and a beach in the background.

13. 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$938
includes taxes & fees
8 Sept - 9 Sept
Marriott's Grande Ocean
A covered outdoor seating area with a view of the sunset over a body of water.

14. 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, (156 reviews)
"Very nice place to stay "
United States
Alejandro
The price is NZ$531
includes taxes & fees
3 Sept - 4 Sept
Marriott's Harbour Point and Sunset Pointe at Shelter Cove
A dining area with a glass table, white chairs, a central plant, and a geometric ceiling light fixture.

15. 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
Walk to Beach: Hilton Head Condo w/ Pool Access
A modern living room with a glass coffee table, a sofa, a white nightstand, and a large mirror.

16. 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$652
includes taxes & fees
22 Sept - 23 Sept
Beachfront Condo w/ Pool Access in Hilton Head!
A dining area with a wooden table, chairs, and a chandelier. There is a painting on the wall and a cabinet with decorative items.

17. Hilton Head Condo: Beach Supplies, Walk to Shore!

Hilton Head Condo: Beach Supplies, Walk to Shore!
3.0 star property
Mid Island
8.4 out of 10, Very good, (5 reviews)
"I’m thrilled with the location of this condo. It’s just a quick walk to the beach, and there are also easy-to-access walking, running, and biking trails. There are plenty of local restaurants, food trucks, grocery stores, and attractions nearby. The only downside is that I didn’t receive the email from Evolve with the check-in/out instructions, as it was delivered to my spam folder. The unit was a bit dusty, probably because it was the off-season when I visited, but a quick trip to the local...
United States
Derval
The price is NZ$533
includes taxes & fees
29 Aug - 30 Aug
Hilton Head Condo: Beach Supplies, Walk to Shore!
A living room with a flat-screen TV, a fireplace, a sofa, and a dining area with a table and chairs.

18. Serene Hilton Head Island Condo w/ Community Pool!

Serene Hilton Head Island Condo w/ Community Pool!
4.0 star property
South End
The price is NZ$731
includes taxes & fees
30 Aug - 31 Aug
Serene Hilton Head Island Condo w/ Community Pool!
A spacious living area with a ceiling fan, a dining table with chairs, a sofa, a coffee table, and a TV mounted on the wall.

19. Oceanfront Condo! Breakers 210 w/ Sunrise Views

Oceanfront Condo! Breakers 210 w/ Sunrise Views
4.0 star property
South End
The price is NZ$787
includes taxes & fees
29 Aug - 30 Aug
Oceanfront Condo! Breakers 210 w/ Sunrise Views

20. Breakers 328 Oceanfront Hilton Head Condo Direct Beach Access

Breakers 328 Oceanfront Hilton Head Condo Direct Beach Access
2.0 star property
South End
The price is NZ$1,176
includes taxes & fees
3 Sept - 4 Sept
Breakers 328 Oceanfront Hilton Head Condo Direct Beach Access
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

The Westin Hilton Head Island Resort & Spa

The Westin Hilton Head Island Resort & Spa

10/10 Excellent
"Great experience. Beautiful beach, 3 pools, friendly non-pushy staff, plenty of pool seating, clean rooms, great fitness center, free water daily, decent food, quality covered self parking. The only negative we noticed is that the hallways in our area were loud because there was laminate floors due to beach/pool access. Walls are a little thin. But, no issue with sleeping at all."
Glenn 3-night trip
Posted 23 hours ago
The Westin Hilton Head Island Resort & Spa

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, 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 NZ$531 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 popular beaches 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. Another good choice for your trip to Hilton Head Island is Custom Built GORGEOUS 5 Bedroom Sea Pines Home w/ Private Pool + Screen Porch.

How many holiday rentals are there in Hilton Head Island?

With 1031 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. 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.