Hilton Head Island Holiday Rentals

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Our top choices for Hilton Head Island holiday rentals

Beachfront Condo w/ Pool Access in Hilton Head!

Beachfront Condo w/ Pool Access in Hilton Head!
4.0 star property
South End
10.0 out of 10, Exceptional, (1 review)
The price is NZ$771
includes taxes & fees
16 May - 17 May
Beachfront Condo w/ Pool Access in Hilton Head!

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, (56 reviews)
"Relaxing and comfortable stay"
United States
cheryl j.
The price is NZ$498
includes taxes & fees
4 May - 5 May
Tranquility by the Beach 1st Fl Sleeps 6,King Bed

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$596
includes taxes & fees
9 May - 10 May
Coastal Cove Villa

Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown

Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown
Sea Pines
10.0 out of 10, Exceptional, (88 reviews)
"Great location!"
United States
Jessica G.
The price is NZ$652
includes taxes & fees
5 May - 6 May
Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown

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, (136 reviews)
"Property was in a great location and everything was clean."
United States
Miranda
The price is NZ$594
includes taxes & fees
16 May - 17 May
Heart of Historic Bluffton BEST LOCATION, Charming Cottage THIS IS THE ONE

Disney's Hilton Head Island Resort

Disney's Hilton Head Island Resort
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (129 reviews)
"While the rooms are overdue a refurbishment, this place is a wondeful resort. "
United States
Chad
Disney's Hilton Head Island Resort

SeaClusion-Oceanview, Mini split AC, Beach Chairs

SeaClusion-Oceanview, Mini split AC, Beach Chairs
South End
9.6 out of 10, Exceptional, (66 reviews)
"Location cleanliness cozy the beach 3min walk its a great spot"
United States
kenneth
The price is NZ$468
includes taxes & fees
25 May - 26 May
SeaClusion-Oceanview, Mini split AC, Beach Chairs

Beach Daze-Gorgeous new shower! Bikes Included

Beach Daze-Gorgeous new shower! Bikes Included
South End
9.6 out of 10, Exceptional, (18 reviews)
"Great road trip with my daughter! The place was perfect "
United States
Nicole H.
Beach Daze-Gorgeous new shower! Bikes Included

Old Town + Modern 4 BR + Fire Pit + EV Charger

Old Town + Modern 4 BR + Fire Pit + EV Charger
Old Town Bluffton
9.4 out of 10, Exceptional, (28 reviews)
"Thank you so much for a wonderful stay!"
United States
Christy R.
The price is NZ$832
includes taxes & fees
3 May - 4 May
Old Town + Modern 4 BR + Fire Pit + EV Charger

2-bedroom condo walking distance to Singleton Beach

2-bedroom condo walking distance to Singleton Beach
Mid Island
9.6 out of 10, Exceptional, (14 reviews)
"We had a great experience! The property is as advertised, clean, welcoming, and in a great location. Communication with the host was excellent and the check in / check out was seamless. "
United States
Joseph C.
The price is NZ$588
includes taxes & fees
31 May - 1 June
2-bedroom condo walking distance to Singleton Beach

Oceanfront Hilton Head Island Condo w/ Pool!

Oceanfront Hilton Head Island Condo w/ Pool!
3.0 star property
South End
9.0 out of 10, Wonderful, (4 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 NZ$594
includes taxes & fees
1 May - 2 May
Oceanfront Hilton Head Island Condo w/ Pool!

Old Town + Walk to restaurant + EV Charger

Old Town + Walk to restaurant + EV Charger
Old Town Bluffton
9.8 out of 10, Exceptional, (23 reviews)
"Great location"
United States
Linda T.
The price is NZ$636
includes taxes & fees
4 May - 5 May
Old Town + Walk to restaurant + EV Charger

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, (148 reviews)
"Ambrose kept me well informed and his condo is lovely. Great beach access -- and great beach!"
United States
Martha H.
The price is NZ$458
includes taxes & fees
3 May - 4 May
Steps from beach. No price increase, low fees. Also #2320603 w panoramic view.

Elegance at the beach -Ocean View Villa, Gorgeous!

Elegance at the beach -Ocean View Villa, Gorgeous!
South End
10.0 out of 10, Exceptional, (111 reviews)
"Our stay was perfect!"
United States
Cathy R.
The price is NZ$458
includes taxes & fees
5 May - 6 May
Elegance at the beach -Ocean View Villa, Gorgeous!

Beachy chic, steps from the beach!

Beachy chic, steps from the beach!
Mid Island
9.4 out of 10, Exceptional, (58 reviews)
"The condo was clean and nicely decorated. The kitchen was well equipped. Great location - just a few minutes walk to the beach. "
United States
Ellen
The price is NZ$585
includes taxes & fees
2 May - 3 May
Beachy chic, steps from the beach!

Luxe Condo in Old Town Bluffton + Elevator + Walkable to everything!

Luxe Condo in Old Town Bluffton + Elevator + Walkable to everything!
Old Town Bluffton
9.8 out of 10, Exceptional, (92 reviews)
"Great place and a very convenient location!"
United States
Anonymous traveller
The price is NZ$832
includes taxes & fees
3 May - 4 May
Luxe Condo in Old Town Bluffton + Elevator + Walkable to everything!

Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view

Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view
South End
9.6 out of 10, Exceptional, (153 reviews)
"Great location. Great host. Would definitely book again. "
United States
Janice G.
The price is NZ$591
includes taxes & fees
13 May - 14 May
Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view

Carriage House within 5 minute walk of Old Town Bluffton

Carriage House within 5 minute walk of Old Town Bluffton
Old Town Bluffton
10.0 out of 10, Exceptional, (80 reviews)
"Great location; carriage house was very nice! Offered everything we needed, very comfortable. Would definitely stay here again; highly recommend! "
United States
Anita
The price is NZ$472
includes taxes & fees
11 May - 12 May
Carriage House within 5 minute walk of Old Town Bluffton

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, (147 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$740
includes taxes & fees
1 May - 2 May
Experience Luxury at the Beach! Oceanside Resort! Huge Oceanside Pool!

Direct Ocean Front First Floor 1BR/1Bath Condo

Direct Ocean Front First Floor 1BR/1Bath Condo
South End
9.2 out of 10, Wonderful, (68 reviews)
"Everything clean and view was amazing. Bed is sleeping on a piece of cheap tan foam on top of mattress. Needs to have a covering or something to keep from feeling it through thin sheets. And the pool and elevator is far on other end of unit. For us no problem but beware if you need elevator. Well kept grounds to beach."
United States
Deborah
Direct Ocean Front First Floor 1BR/1Bath Condo
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$496 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?

Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown: This highly rated holiday home rental in Hilton Head Island is located on the beach, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Other favourite homes for rent in Hilton Head Island are Beach. View. Suite. 1 br. 1 ba. Sleeps 5 and Warm Natural Light, Expansive Back Deck w/ Sectional Seating, Golf Course Views & Community Pool.

How many holiday rentals are there in Hilton Head Island?

With 933 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 Coastal Discovery Museum and Coligny Theater, whereas Coligny Beach and Sea Pines Forest Preserve are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include The Sandbox and Shipyard Golf Course.

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.