Hilton Head Island Holiday Rentals

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Our top choices for Hilton Head Island holiday rentals

Oceanfront Breakers 137 Condo w/ Sunrise Views!

Oceanfront Breakers 137 Condo w/ Sunrise Views!
3.5 star property
South End
The price is NZ$731
includes taxes & fees
15 Apr - 16 Apr
Oceanfront Breakers 137 Condo w/ Sunrise Views!

Disney's Hilton Head Island Resort

Disney's Hilton Head Island Resort
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (128 reviews)
"While the rooms are overdue a refurbishment, this place is a wondeful resort. "
United States
Chad
Disney's Hilton Head Island Resort

Marriott's Grande Ocean

Marriott's Grande Ocean
3.5 star property
South End
9.4 out of 10, Exceptional, (173 reviews)
"Very clean room, warm pools, excellent location! "
United States
Sean
The price is NZ$1,162
includes taxes & fees
14 Apr - 15 Apr
Marriott's Grande Ocean

2BD/2BATH Villa! Near Beach! HHR Building 3!

2BD/2BATH Villa! Near Beach! HHR Building 3!
Mid Island
9.4 out of 10, Exceptional, (11 reviews)
"Met all expectations "
United States
Bradley
The price is NZ$628
includes taxes & fees
3 May - 4 May
2BD/2BATH Villa! Near Beach! HHR Building 3!

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, (55 reviews)
"Relaxing and comfortable stay"
United States
cheryl j.
The price is NZ$530
includes taxes & fees
3 May - 4 May
Tranquility by the Beach 1st Fl Sleeps 6,King Bed

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, (146 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$736
includes taxes & fees
5 Apr - 6 Apr
Experience Luxury at the Beach! Oceanside Resort! Huge Oceanside Pool!

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)
"The home and the amenities were perfect for our needs. Would highly recommend."
United States
Sean F.
The price is NZ$1,269
includes taxes & fees
5 Apr - 6 Apr
Old Town + Modern 4 BR + Fire Pit + EV Charger

Coastal Chic Hilton Head Beach & Tennis A342 w/ Pickleball, Pools & Restaurants

Coastal Chic Hilton Head Beach & Tennis A342 w/ Pickleball, Pools & Restaurants
Mid Island
9.2 out of 10, Wonderful, (38 reviews)
"Nice secluded location and easy beach access "
United States
Maegan
The price is NZ$516
includes taxes & fees
3 Apr - 4 Apr
Coastal Chic Hilton Head Beach & Tennis A342 w/ Pickleball, Pools & Restaurants

Marriott's Harbour Club

Marriott's Harbour Club
3.5 star property
Sea Pines
9.0 out of 10, Wonderful, (63 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 NZ$740
includes taxes & fees
13 Apr - 14 Apr
Marriott's Harbour Club

Super-Cute Villa with Ocean View and Two Bikes!

Super-Cute Villa with Ocean View and Two Bikes!
South End
9.6 out of 10, Exceptional, (100 reviews)
"great location, on the beach!"
United States
Jay J.
The price is NZ$525
includes taxes & fees
7 Apr - 8 Apr
Super-Cute Villa with Ocean View and Two Bikes!

'wright by the Beach': Hilton Head Condo w/ Perks

'wright by the Beach': Hilton Head Condo w/ Perks
3.0 star property
Mid Island
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay. We loved the ocean theme at the apartment. Very clean rooms. Kids enjoyed swimming in the indoor pool, parents enjoyed hot tub and sauna especially on rainy days. They have indoor and outdoor pools. We liked walking on the boardwalk to the beach. We highly recommend this place and would love to return there again. "
United States
Victor
The price is NZ$477
includes taxes & fees
13 Apr - 14 Apr
'wright by the Beach': Hilton Head Condo w/ Perks

2 Bedroom Lovely Comfort - Oceanfront Resort - King Bed - Beach & Tennis D12

2 Bedroom Lovely Comfort - Oceanfront Resort - King Bed - Beach & Tennis D12
Mid Island
9.6 out of 10, Exceptional, (44 reviews)
"Property is nice and easy to get to, and was clean."
United States
Andrew M.
The price is NZ$797
includes taxes & fees
3 Apr - 4 Apr
2 Bedroom Lovely Comfort - Oceanfront Resort - King Bed - Beach & Tennis D12

Marriott's SurfWatch

Marriott's SurfWatch
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (196 reviews)
"Very clean room and resort "
United States
Larisa
The price is NZ$1,008
includes taxes & fees
13 Apr - 14 Apr
Marriott's SurfWatch

SeaClusion-Oceanview, Mini split AC, Beach Chairs

SeaClusion-Oceanview, Mini split AC, Beach Chairs
South End
9.6 out of 10, Exceptional, (61 reviews)
"Location cleanliness cozy the beach 3min walk its a great spot"
United States
kenneth
The price is NZ$465
includes taxes & fees
16 Apr - 17 Apr
SeaClusion-Oceanview, Mini split AC, Beach Chairs

Elegance at the beach -Ocean View Villa, Gorgeous!

Elegance at the beach -Ocean View Villa, Gorgeous!
South End
10.0 out of 10, Exceptional, (108 reviews)
"Our stay was perfect!"
United States
Cathy R.
The price is NZ$482
includes taxes & fees
5 Apr - 6 Apr
Elegance at the beach -Ocean View Villa, Gorgeous!

Brand New As Seen on HGTV! Deluxe Beachfront Villa W/ Beautiful Ocean Views

Brand New As Seen on HGTV! Deluxe Beachfront Villa W/ Beautiful Ocean Views
South End
8.4 out of 10, Very good, (72 reviews)
"Great location and beautiful condo. Would recommend! "
United States
Tawni O.
The price is NZ$958
includes taxes & fees
15 Apr - 16 Apr
Brand New As Seen on HGTV! Deluxe Beachfront Villa W/ Beautiful Ocean Views

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$940
includes taxes & fees
27 Apr - 28 Apr
Old Town + Walk to restaurant + EV Charger

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

Bluffton Retreat, Pet Friendly

Bluffton Retreat, Pet Friendly
Bluffton
10.0 out of 10, Exceptional, (21 reviews)
"Host was very responsive to our needs."
United States
Margie S.
The price is NZ$595
includes taxes & fees
16 Apr - 17 Apr
Bluffton Retreat, Pet Friendly

Barefoot Bungalow! Ocean View Couple’s Retreat

Barefoot Bungalow! Ocean View Couple’s Retreat
South End
10.0 out of 10, Exceptional, (192 reviews)
"Everything was what it was presented to be, an increasingly rare thing these days. The host was attentive without being in any way intrusive, even giving notice of a water main problem so we would not be surprised. "
United States
Walter
The price is NZ$545
includes taxes & fees
6 Apr - 7 Apr
Barefoot Bungalow! Ocean View Couple’s Retreat
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$572 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?

Beach. View. Suite. 1 br. 1 ba. Sleeps 5: This highly rated holiday home rental in Hilton Head Island is located on the beach, and has an outdoor pool, a balcony and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a garden. Other favourite homes for rent in Hilton Head Island are Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380 and Custom Built GORGEOUS 5 Bedroom Sea Pines Home w/ Private Pool + Screen Porch.

How many holiday rentals are there in Hilton Head Island?

With 964 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 Heron Point by Pete Dye at Sea Pines Resort 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.