Hilton Head Island Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Hilton Head Island holiday rentals

Interior

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 HK$1,324
HK$3,486 total
includes taxes & fees
16 May - 17 May
Beachfront Condo w/ Pool Access in Hilton Head!
On the beach

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 HK$836
HK$2,316 total
includes taxes & fees
7 May - 8 May
Tranquility by the Beach 1st Fl Sleeps 6,King Bed
Interior

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 HK$865
HK$2,546 total
includes taxes & fees
5 May - 6 May
Coastal Cove Villa
Smart TV, books

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, (89 reviews)
"Great location!"
United States
Jessica G.
The price is HK$1,220
HK$2,997 total
includes taxes & fees
5 May - 6 May
Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown
Exterior

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 HK$1,378
HK$2,756 total
includes taxes & fees
5 May - 6 May
Heart of Historic Bluffton BEST LOCATION, Charming Cottage THIS IS THE ONE
Snack bar

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)
"The room and property were incredible! Already booking my next stay"
United States
Melissa
Disney's Hilton Head Island Resort
Interior

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 HK$713
HK$2,120 total
includes taxes & fees
25 May - 26 May
SeaClusion-Oceanview, Mini split AC, Beach Chairs
Property grounds

Beach Daze-Gorgeous new shower! Bikes Included

Beach Daze-Gorgeous new shower! Bikes Included
South End
9.6 out of 10, Exceptional, (19 reviews)
"Great road trip with my daughter! The place was perfect "
United States
Nicole H.
Beach Daze-Gorgeous new shower! Bikes Included
Beach nearby

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 HK$1,563
HK$3,925 total
includes taxes & fees
10 May - 11 May
Old Town + Modern 4 BR + Fire Pit + EV Charger
Bar (on property)

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 HK$705
HK$1,887 total
includes taxes & fees
4 May - 5 May
2-bedroom condo walking distance to Singleton Beach
Interior

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
Oceanfront Hilton Head Island Condo w/ Pool!
Beach nearby

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 HK$973
HK$2,758 total
includes taxes & fees
4 May - 5 May
Old Town + Walk to restaurant + EV Charger
On the beach, sun-loungers, beach towels

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 HK$846
HK$2,137 total
includes taxes & fees
4 May - 5 May
Steps from beach. No price increase, low fees. Also #2320603 w panoramic view.
Property grounds

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 HK$662
HK$2,047 total
includes taxes & fees
5 May - 6 May
Elegance at the beach -Ocean View Villa, Gorgeous!
On the beach, sun-loungers

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
Beachy chic, steps from the beach!
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 HK$1,340
HK$3,546 total
includes taxes & fees
11 May - 12 May
Luxe Condo in Old Town Bluffton + Elevator + Walkable to everything!
Terrace/patio

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 HK$1,481
HK$2,741 total
includes taxes & fees
11 May - 12 May
Free Bikes, Parking & WiFi, Perfect couple's getaway villa with ocean view
TV

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, (81 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 HK$881
HK$2,168 total
includes taxes & fees
4 May - 5 May
Carriage House within 5 minute walk of Old Town Bluffton
On the beach, sun-loungers

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, (148 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 HK$1,528
HK$3,620 total
includes taxes & fees
10 May - 11 May
Experience Luxury at the Beach! Oceanside Resort! Huge Oceanside Pool!
Property grounds

Direct Ocean Front First Floor 1BR/1Bath Condo

Direct Ocean Front First Floor 1BR/1Bath Condo
South End
9.2 out of 10, Wonderful, (69 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
The price is HK$917
HK$2,680 total
includes taxes & fees
11 May - 12 May
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

The Westin Hilton Head Island Resort & Spa

The Westin Hilton Head Island Resort & Spa

8/10 Good
"Clean and comfortable. Stopped for one night on travels home from Florida. Disappointed in room service menu and lack of options for GF as we arrived later and were too tired to go out. Also, coffee in room needs more than 2 pods. A LONG walk to the elevator as that’s not convenient in morning coffee shop open and was able to get coffee before heading home. Beds comfy as per usual. We didn’t get to see the beach or tour the hotel this visit."
Melanie 1-night trip
Posted 1 hour ago
The Westin Hilton Head Island Resort & Spa

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
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  • 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 holiday rentals in Hilton Head Island?

Yes, there are holiday rentals in Hilton Head Island close to Coastal Discovery Museum, 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 Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown 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 944 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 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.