Hilton Head Island Holiday Rentals

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Our top choices for Hilton Head Island holiday rentals

Condo resort in Mid Island

Marriott's Barony Beach Club
3.5 star property
9.6 out of 10, Exceptional, (243)
"Great place for vacation on the beach, nice, clean and quiet areas "
United States
Larisa
The price is NZ$351
includes taxes & fees
6 Jan - 7 Jan 2026
Marriott's Barony Beach Club
2.0 star property
10.0 out of 10, Exceptional, (4)
"Great central location for our trip, plenty of sleeping options (family of 5) and very clean. Host was excellent to coordinate with and check-in was a breeze!"
United States
Brian J.
The price is NZ$497
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy 2-bedroom villa close to Coligny!
2.0 star property
8.0 out of 10, Very good, (2)
"No proper communication and things broke inside or not working "
United States
Alejandra
The price is NZ$533
includes taxes & fees
4 Jan - 5 Jan 2026
Beach Getaway 2BR w/ Pool + Modern Comforts

Holiday Home in Sea Pines

Marriott's Harbour Club
3.5 star property
9.2 out of 10, Wonderful, (61)
"The staff was extremely inviting, professional, and kind. Parking was extremely easy we stayed in villa 3939. It was very large, clean, and had a great view. The property was conveniently located within the area and very walkable. It is very dark at night but we felt safe walking back from dinner. I’d definitely recommend this property for a quiet and peaceful getaway."
United States
ANGELEE
The price is NZ$385
includes taxes & fees
1 Jan - 2 Jan 2026
Marriott's Harbour Club

Holiday Home in Mid Island

Disney's Hilton Head Island Resort
3.5 star property
9.6 out of 10, Exceptional, (127)
"While the rooms are overdue a refurbishment, this place is a wondeful resort. "
United States
Chad
Disney's Hilton Head Island Resort
3.5 star property
8.6 out of 10, Excellent, (98)
"It was perfect for our needs. Check-in was super easy!"
United States
Melanie
Ocean Palms Villas at Port Royal Resort

Aparthotel in South End

Players Club Resort
4.0 star property
8.0 out of 10, Very good, (10)
"Clean, safe, and relaxing location. Enjoyed the beach and local restaurants. "
United States
Melvin
The price is NZ$395
includes taxes & fees
16 Jan - 17 Jan 2026
Players Club Resort
9.4 out of 10, Exceptional, (3)
"The unit was comfortable, clean and quiet and just as portrayed in the listing. I will definitely intend to book again in the future."
United States
Howard B.
The price is NZ$369
includes taxes & fees
5 Jan - 6 Jan 2026
NEW! 1 BD Apt~Beach Access~Clean~Great Location~Quiet & NICE! Great for Couples!
10.0 out of 10, Exceptional, (77)
"Great stay!"
United States
Julie H.
The price is NZ$1,031
includes taxes & fees
19 Jan - 20 Jan 2026
Quiet Tide is a 4bd 3 bath condo located in South Forest Beach
9.8 out of 10, Exceptional, (26)
"Great place, clean, updated and great proximity to the beach, shops and restaurants. Holly was amazing at communication during our trip."
United States
Mike M.
The price is NZ$491
includes taxes & fees
31 Dec - 1 Jan 2026
Condo w/ Pool 2BR Close to beach Free WiFi

Condo resort in South End

Marriott's Grande Ocean
3.5 star property
9.4 out of 10, Exceptional, (164)
"Great room and amenities. Unfortunately, we had a poor experience with the front desk at checkout. Took 5 stars directly to 3 . "
United States
Patrick
The price is NZ$398
includes taxes & fees
7 Jan - 8 Jan 2026
Marriott's Grande Ocean
8.6 out of 10, Excellent, (10)
"Very clean place and good location. Excellent communication from host. Highly recommend."
United States
WENDY O.
The price is NZ$387
includes taxes & fees
11 Jan - 12 Jan 2026
Sweet Nest Bluffton Cottage • Fenced in yard • Pet-Friendly • Gazebo • Private
9.2 out of 10, Wonderful, (90)
"Everything was absolutely perfect! We had an amazing little weekend of family fun. Definitely coming back. "
United States
Josie J.
The price is NZ$464
includes taxes & fees
4 Jan - 5 Jan 2026
Walk to beach, indoor/outdoor pools, washer/dryer

Holiday Home in Sea Pines

Marriott's Heritage Club
3.5 star property
9.4 out of 10, Exceptional, (67)
"Another great Marriott, super clean and spacious with the comforts we needed to finish out a long trip (e.g. hot tub, laundry, kitchen). Friendly staff and convenient to the forest reserve."
United States
Landry
The price is NZ$307
includes taxes & fees
5 Jan - 6 Jan 2026
Marriott's Heritage Club
9.4 out of 10, Exceptional, (53)
"Had a great time. Location was great about a 2 minute walk to beach. Condo was great"
United States
Anonymous traveller
The price is NZ$490
includes taxes & fees
18 Jan - 19 Jan 2026
Beachy chic, steps from the beach!
9.4 out of 10, Exceptional, (48)
"Condo was exactly as listed. Owner was very nice and helpful. We stay at this resort often and we really enjoy it."
United States
Carrie D.
The price is NZ$605
includes taxes & fees
11 Jan - 12 Jan 2026
Lagoon View Resort Villa - Walk to the Beach!
10.0 out of 10, Exceptional, (96)
"The property was great for our needs, close to the beach, restaurants and biking trails. Owners were very easy to work with and very accommodating!"
United States
Kristin
The price is NZ$536
includes taxes & fees
31 Dec - 1 Jan 2026
Castaways King Villa on Beach, Free Bikes!
10.0 out of 10, Exceptional, (29)
"Perfect place to have a relaxing and wonderful vacation."
United States
Robert W.
The price is NZ$1,024
includes taxes & fees
11 Jan - 12 Jan 2026
Quiet villa with Fast-reliable internet for distance learning and teleworking
10.0 out of 10, Exceptional, (151)
"Great location, easy beach access, and super clean condo! Definitely would stay again."
United States
Brett H.
Make Coligny Beach Your Happy Place!!
9.6 out of 10, Exceptional, (213)
"Property was nice and clean. Instructions were detailed and everything was fantastic. The "
United States
Amber M.
The price is NZ$411
includes taxes & fees
4 Jan - 5 Jan 2026
5th Villa to Beach Remodeled for 2021- Steps to Open Beach ** SLEEPS 7 **
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

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$300 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. 

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?

Fall Winter Escape: Value for Golf/Tennis/Pickleball Family Getaways best Locale: This highly rated holiday home rental in Hilton Head Island is located near the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Other favourite homes for rent in Hilton Head Island are Island Escape! Pool, Elevator, Pinball, Foosball, Arcade, Nursery,Infrared Sauna and 5 ⭐️ property! Private pool!!SHORT walk to beach!! ❤️ of Sea Pines. Sleeps 12.

How many holiday rentals are there in Hilton Head Island?

With 898 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. Other places in town to visit include Shipyard Golf Course and Coligny Plaza.

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.