Hilton Head Island Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

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

Tranquility by the Beach 1st Fl Sleeps 6,King Bed

Tranquility by the Beach 1st Fl Sleeps 6,King Bed
Mid Island
9.4 out of 10, Exceptional, (57 reviews)
"Relaxing and comfortable stay"
United States
cheryl j.
The price is NZ$510
includes taxes & fees
20 May - 21 May
Tranquility by the Beach 1st Fl Sleeps 6,King Bed

Oceanfront Breakers 137 Condo w/ Sunrise Views!

Oceanfront Breakers 137 Condo w/ Sunrise Views!
3.5 star property
South End
The price is NZ$755
includes taxes & fees
9 June - 10 June
Oceanfront Breakers 137 Condo w/ Sunrise Views!

1805 Bluff Villas at The Sea Pines Resort

1805 Bluff Villas at The Sea Pines Resort
3.0 star property
Sea Pines
10.0 out of 10, Exceptional, (1 review)
"Didn’t use the pool. Closed. Bummed about that. "
United States
RACHEL
1805 Bluff Villas at The Sea Pines Resort

SeaClusion-Oceanview, Mini split AC, Beach Chairs

SeaClusion-Oceanview, Mini split AC, Beach Chairs
South End
9.6 out of 10, Exceptional, (67 reviews)
"Location cleanliness cozy the beach 3min walk its a great spot"
United States
kenneth
The price is NZ$456
includes taxes & fees
21 May - 22 May
SeaClusion-Oceanview, Mini split AC, Beach Chairs

Heart of Historic Bluffton BEST LOCATION, Charming Cottage THIS IS THE ONE

Heart of Historic Bluffton BEST LOCATION, Charming Cottage THIS IS THE ONE
Old Town Bluffton
9.4 out of 10, Exceptional, (138 reviews)
"Property was in a great location and everything was clean."
United States
Miranda
The price is NZ$593
includes taxes & fees
18 May - 19 May
Heart of Historic Bluffton BEST LOCATION, Charming Cottage THIS IS THE ONE

Bluffton Retreat, Pet Friendly

Bluffton Retreat, Pet Friendly
Bluffton
9.8 out of 10, Exceptional, (26 reviews)
"Host was very responsive to our needs."
United States
Margie S.
The price is NZ$624
includes taxes & fees
20 May - 21 May
Bluffton Retreat, Pet Friendly

Experience Luxury at the Beach! Oceanside Resort! Huge Oceanside Pool!

Experience Luxury at the Beach! Oceanside Resort! Huge Oceanside Pool!
Mid Island
10.0 out of 10, Exceptional, (150 reviews)
"Property was clean, inviting, well apportioned and exactly as advertised. Close to beach and pool. Nice location. "
United States
Gene C.
The price is NZ$745
includes taxes & fees
18 May - 19 May
Experience Luxury at the Beach! Oceanside Resort! Huge Oceanside Pool!

Sandy Feet Retreat-New Shower-Bikes Incl-Oceanview

Sandy Feet Retreat-New Shower-Bikes Incl-Oceanview
South End
10.0 out of 10, Exceptional, (121 reviews)
"Great communication. Perfect location, spotless unit. "
United States
Maureen S.
The price is NZ$466
includes taxes & fees
20 May - 21 May
Sandy Feet Retreat-New Shower-Bikes Incl-Oceanview

Great Panoramic Views meet Beach Modern Chic !

Great Panoramic Views meet Beach Modern Chic !
Mid Island
8.8 out of 10, Excellent, (59 reviews)
"The condo was absolutely perfect. Newly renovated and beautiful. We hope to stay there again! The only downside was the broken elevator in the building, but we made it work!"
United States
Marissa
The price is NZ$604
includes taxes & fees
18 May - 19 May
Great Panoramic Views meet Beach Modern Chic !

Steps from beach. No price increase, low fees. Also #2320603 w panoramic view.

Steps from beach. No price increase, low fees. Also #2320603 w panoramic view.
Mid Island
10.0 out of 10, Exceptional, (150 reviews)
"This place was exceptional! Everything was just as the ad said. Hosts were remarkable with communication and precise check in info. A wonderful place to vacation. It was literally steps from the beach. My two teenage grandsons loved all the amenities that the resort offered. There was so much to do! I particularly liked the private beach access. Not too crowded and loved, LOVED the rooms decor! It was a pleasure to be able to rent this place. Ambrose and Barbie have a perfect little get away and...
United States
L
The price is NZ$467
includes taxes & fees
19 May - 20 May
Steps from beach. No price increase, low fees. Also #2320603 w panoramic view.

Newly Updated, Near Harbour Town 1st Floor 2 Bedroom 2Bath Villa

Newly Updated, Near Harbour Town 1st Floor 2 Bedroom 2Bath Villa
Sea Pines
9.4 out of 10, Exceptional, (68 reviews)
"Jorge’s place was amazing, close to harbor town, and very spacious! Everything was stocked well and great communication! We’d stay here every time!"
United States
Gloria M.
The price is NZ$928
includes taxes & fees
18 May - 19 May
Newly Updated, Near Harbour Town 1st Floor 2 Bedroom 2Bath Villa

Bluffton Getaway w/ Fenced Yard: 7 Mi to Beach!

Bluffton Getaway w/ Fenced Yard: 7 Mi to Beach!
3.0 star property
Edgefield
10.0 out of 10, Exceptional, (1 review)
"It was like home away frim home. "
United States
Willie
The price is NZ$881
includes taxes & fees
24 May - 25 May
Bluffton Getaway w/ Fenced Yard: 7 Mi to Beach!

Oceanfront & Across from Coligny-Walk Everywhere!

Oceanfront & Across from Coligny-Walk Everywhere!
South End
9.8 out of 10, Exceptional, (133 reviews)
"We had a really nice stay! Great location "
United States
Stefanie
The price is NZ$731
includes taxes & fees
1 June - 2 June
Oceanfront & Across from Coligny-Walk Everywhere!

Beautiful Remodeled Seascape Villa-Pool, Beach, Coligny Plaza, Celebration Park!

Beautiful Remodeled Seascape Villa-Pool, Beach, Coligny Plaza, Celebration Park!
South End
8.6 out of 10, Excellent, (28 reviews)
"My family and I had a nice stay. "
United States
Jim M.
The price is NZ$695
includes taxes & fees
19 May - 20 May
Beautiful Remodeled Seascape Villa-Pool, Beach, Coligny Plaza, Celebration Park!

Beauty at the Beach! Oceanview King bed free bikes

Beauty at the Beach! Oceanview King bed free bikes
South End
9.8 out of 10, Exceptional, (45 reviews)
"The host was very helpful! The place was very clean. "
United States
cindy p.
Beauty at the Beach! Oceanview King bed free bikes

Coastal Cove Villa

Coastal Cove Villa
South End
9.8 out of 10, Exceptional, (6 reviews)
"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$598
includes taxes & fees
26 May - 27 May
Coastal Cove Villa

SOUTH FOREST BEACH. Coligny, pool. walk to beach. updated. sleep 8. SURF COURT

SOUTH FOREST BEACH. Coligny, pool. walk to beach. updated. sleep 8. SURF COURT
South End
9.2 out of 10, Wonderful, (75 reviews)
"Perfect spot. The beach and especially pool were a short walk for our young family."
United States
William B.
The price is NZ$1,157
includes taxes & fees
18 May - 19 May
SOUTH FOREST BEACH. Coligny, pool. walk to beach. updated. sleep 8. SURF COURT

Old Town + Walk to restaurant + EV Charger

Old Town + Walk to restaurant + EV Charger
Old Town Bluffton
9.8 out of 10, Exceptional, (24 reviews)
"Great location"
United States
Linda T.
The price is NZ$586
includes taxes & fees
18 May - 19 May
Old Town + Walk to restaurant + EV Charger

Oceanfront with easy beach access, large pool, and tiki bar/restaurant!

Oceanfront with easy beach access, large pool, and tiki bar/restaurant!
Mid Island
9.6 out of 10, Exceptional, (105 reviews)
"It was very clean and had a good view. The owner was prompt on communication and helping with every question I had. "
United States
Macey B.
The price is NZ$606
includes taxes & fees
18 May - 19 May
Oceanfront with easy beach access, large pool, and tiki bar/restaurant!

FANTASTIC Villa on #2 Green of Famed Harbour Town Golf Links!

FANTASTIC Villa on #2 Green of Famed Harbour Town Golf Links!
Sea Pines
9.8 out of 10, Exceptional, (132 reviews)
"The condo was exactly as advertised!! Parking was always available right in front of the unit. Location is fabulous!! Walked down to Harbor Town multiple times to watch the sunset. Drive to the beach every morning!! Looking out in the golf course is beautiful!! We thoroughly enjoyed our stay. "
United States
Rebecca P.
The price is NZ$891
includes taxes & fees
30 May - 31 May
FANTASTIC Villa on #2 Green of Famed Harbour Town Golf Links!
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.
Save an average of 15% on thousands of hotels when you're signed in

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$462 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 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?

Beautiful 2nd Row Home, Steps to the Beach, Close to Coligny Private Pool Hot Tub: This highly rated holiday home rental in Hilton Head Island is located near the beach, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub. Other favourite homes for rent in Hilton Head Island are Great Beach House-2 min. Walk to Beach, Private Splash Pool, Gas Grill, 5 min. Walk to Coligny Plaza and Periwinkle Point | Private Pool - Walk to Beach.

How many holiday rentals are there in Hilton Head Island?

With 969 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 Coligny Theater and Arts Center of Coastal Carolina, 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.