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. 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$364
includes taxes & fees
8 Nov - 9 Nov
Marriott's Monarch at Sea Pines

2. 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$282
includes taxes & fees
3 Nov - 4 Nov
Marriott's Heritage Club

3. 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.
Luxury Penthouse near Beach, Tiki Hut, Coligny

4. 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, (86 reviews)
"This condo has a nice view, but that's about all it has going for it. It's very small...I think it would be too crowded for more than 2 people. It was adequately furnished, but the sofa, chair, and footstools were badly stained. The bed was comfy, but there was a bad odor in the apt. The property management company was pleasant to deal with."
United States
Patsy
The price is NZ$576
includes taxes & fees
12 Nov - 13 Nov
Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

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

Beachfront Condo w/ Pool Access in Hilton Head!
South End
9.2 out of 10, Wonderful, (94 reviews)
"Ocean view was great! The pool was well maintained, warm and with a good amount of chairs. Super close to Coligny beach and shops! Loved our time there and will be back! "
United States
Gary B.
The price is NZ$681
includes taxes & fees
15 Oct - 16 Oct
Beachfront Condo w/ Pool Access in Hilton Head!

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

Palm Breezy Living-Coligny+Bikes included-#228
South End
9.8 out of 10, Exceptional, (174 reviews)
"The location was exceptional, offering immediate access to the beach and proximity to various dining establishments. I would definitely stay here again."
United States
Mayra S.
Palm Breezy Living-Coligny+Bikes included-#228

7. 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$790
includes taxes & fees
19 Oct - 20 Oct
Steps to Beach-hilton Head Condo-pet Friendly

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

Coligny Beach, Pools, & Shops- Few Steps Away
South End
9.6 out of 10, Exceptional, (96 reviews)
"Great Location. Was very clean and accommodating."
United States
Cheryl M.
Coligny Beach, Pools, & Shops- Few Steps Away

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

Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116
Mid Island
9.6 out of 10, Exceptional, (118 reviews)
"Short, but enjoyable stay. Would stay again!"
United States
Dora D.
The price is NZ$577
includes taxes & fees
25 Oct - 26 Oct
Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116

10. Oceanfront Hilton Head Island Condo w/ Pool!

Oceanfront Hilton Head Island Condo w/ Pool!
3.0 star property
South End
8.8 out of 10, Excellent, (6 reviews)
"Nice!! Location great, easy instructions on entry access, nice side view of the ocean from the balcony, the host Meagan was so very nice and accommodating, very close to restaurants and stores, would love to stay here again, Thanks a million!!!! ;)"
United States
Beverly
Oceanfront Hilton Head Island Condo w/ Pool!

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$547
includes taxes & fees
1 Nov - 2 Nov
Marriott's Grande Ocean

12. 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$280
includes taxes & fees
8 Nov - 9 Nov
Marriott's Harbour Club

13. 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, (181 reviews)
"Amazing place to vacation. Loved the view. Beach paradise extremely clean, quiet, easy beach access."
United States
Linda P.
The price is NZ$486
includes taxes & fees
19 Oct - 20 Oct
Flip Flop Paradise-Steps to the Sand! Free Bikes

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

Coral Paradise, Ocean View, Couple's Seaside Retreat, Pool, Walk to Shops Dining
South End
10.0 out of 10, Exceptional, (12 reviews)
"The villa is perfectly located within walking distance to Coligny Plaza and the provided wagon to take to the beach was wonderful! Will definitely stay again when I return to HHI!"
United States
Candice L.
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!!!

Ocean View Villa with Amazing Resort Amenities -- just steps from the beach!!!
South End
9.4 out of 10, Exceptional, (235 reviews)
"Location was absolutely fabulous. Apartment clean, comfortable. A few general maintenance issues, but host responded very promptly. Looking forward to staying again!"
United States
Caitlin
The price is NZ$683
includes taxes & fees
2 Nov - 3 Nov
Ocean View Villa with Amazing Resort Amenities -- just steps from the beach!!!

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

Serene Tides & Relaxing Sunny Days Retreat-Coligny+ Bikes-#233!
South End
9.8 out of 10, Exceptional, (161 reviews)
"Place was excellent."
United States
Amanda F.
Serene Tides & Relaxing Sunny Days Retreat-Coligny+ Bikes-#233!

17. 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

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

Elegance at the beach -Ocean View Villa, Gorgeous!
South End
10.0 out of 10, Exceptional, (130 reviews)
"Property is just as described, clean and so close to the beach! Kendall was so easy to get in touch with. Loved our stay and will definitely stay again."
United States
LeeAnn E.
Elegance at the beach -Ocean View Villa, Gorgeous!

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

Direct Ocean Front First Floor 1BR/1Bath Condo
South End
9.2 out of 10, Wonderful, (82 reviews)
"Megan was a good host. The unit was nice and clean and the beach view was amazing!"
United States
Betty H.
The price is NZ$1,135
includes taxes & fees
17 Oct - 18 Oct
Direct Ocean Front First Floor 1BR/1Bath Condo

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

Beachfront Condo w/ Pool Access in Hilton Head!
4.0 star property
South End
8.0 out of 10, Very good, (3 reviews)
"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...
United States
Manuel
The price is NZ$687
includes taxes & fees
15 Oct - 16 Oct
Beachfront Condo w/ Pool Access in Hilton Head!
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 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.