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

Hilton Head Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Hilton Head Island vacation rentals

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

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, (133 reviews)
"After a booking mixup on what Expedia had listed & what the property details were.. we were happily surprised that the staff & GM made an exception for our reservation. Everyone was very helpful, room was great, clean, great outdoor spaces & easy beach access."
United States
Cory
The price is NT$4,695
NT$5,164 total
includes taxes & fees
Dec 6 - Dec 7
Marriott's Monarch at Sea Pines
A hotel entrance with a covered walkway, a staircase, and a landscaped area with trees and shrubs.

2. Marriott's Harbour Club

Marriott's Harbour Club
3.5 star property
Sea Pines
9.0 out of 10, Wonderful, (64 reviews)
"We are vacation club owner and we extended our stay with Hotels.com Harbor Club is our favorite property on HHI. "
United States
Mark
The price is NT$4,051
NT$4,456 total
includes taxes & fees
Dec 7 - Dec 8
Marriott's Harbour Club
A neatly made bed with a wooden headboard, a ceiling fan, and a wall-mounted fish decoration.

3. 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
The price is NT$2,922
NT$9,841 total
includes taxes & fees
Nov 9 - Nov 10
Oceanfront Hilton Head Island Condo w/ Pool!
A waterfront restaurant with outdoor seating and a view of the water.

4. 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
A covered outdoor seating area with a view of the sunset over a body of water.

5. 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, (159 reviews)
"It was a very nice vacation club. They had activities planned throughout the day that you could attend if you’d like. My kids really enjoyed themselves."
United States
Gary T
The price is NT$2,856
NT$3,142 total
includes taxes & fees
Nov 30 - Dec 1
Marriott's Harbour Point and Sunset Pointe at Shelter Cove
A spacious living area with a high ceiling, large windows, and a central seating arrangement.

6. 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 NT$4,216
NT$4,637 total
includes taxes & fees
Dec 2 - Dec 3
Marriott's Heritage Club
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.
View all properties
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

Beach House Resort Hilton Head

Beach House Resort Hilton Head

8/10 Good
"Great place and excellent location, but unfortunately, our experience was disappointing due to the lack of attention from staff and security. We stayed in an ocean-view room on the fourth floor. The property had clearly posted no-smoking signs and designated smoking areas, with hefty fines for violations. Despite this, cigarette smoke repeatedly came into our room whenever we opened the sliding door. After investigating, we strongly suspected the guests directly above us were smoking. We reported this to the front desk multiple times, but they insisted the smoke was coming from the designated smoking area near the bar. We explained that we continued smelling it even after the bar had closed. Security came to our room, and we specifically told them where we believed it was coming from. Again, they blamed the bartender rather than properly investigating. The following morning, we saw the guests above us smoking, confirming exactly what we had been reporting. Had security simply taken the time to investigate, this could have been resolved. The lack of follow-through and basic due diligence was extremely frustrating. It affected our enjoyment of the stay, as we couldn't leave our sliding door open and enjoy the ocean air without cigarette smoke filling our room. It's a shame because the property and location are great. Management needs to take its smoking policies seriously and ensure staff and security actually enforce them."
Anthony 3-night trip
Posted less than an hour ago
Beach House Resort Hilton Head

Find out more about Hilton Head Island

Search for holiday rentals in Hilton Head Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Hilton Head Island using one of the methods below:

  • View our selection of featured holiday rentals in Hilton Head Island
  • Use the map to find apartments and other holiday homes in the Hilton Head Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hilton Head Island while they last

Look no further and take a look at our great range of rental properties in Hilton Head Island!

Frequently asked questions

Are there vacation rentals in Hilton Head Island?

Yes, you can find vacation rentals in Hilton Head Island close to The Sandbox, or you can select a 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.

How many vacation rentals are there in Hilton Head Island?

With 986 Expedia vacation rentals, you're sure 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 vacation rental in Hilton Head Island like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Hilton Head Island. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for small groups.