Hilton Head Island holiday rentals

We found 10,384 holiday rentals — enter your dates for availability
Select from 1031 houses, 40 apartments and other holiday rentals to find the perfect place for your stay in Hilton Head Island. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the amenities that you expect and more, which might include parking and a garden. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Hilton Head Island

Showing deals for:27 Nov - 4 Dec

Spacious open-concept layout, perfect for group gatherings and socializing
Hilton Head Island - Shelter Cove Harbour & Marina
The open-concept living area flows effortlessly into the kitchen and dining space, creating a perfect gathering spot for everyone.
Direct access from the balcony going to the fenced pool.
Wonderful
(5 reviews)

23 Bradley Circle @ Bradley Beach | Ocean-View Deck | Private Heated Pool | Sleeps 20

Hilton Head Island

6% off
S$10,538
for 7 nights, 1 home
S$1,505 per night
includes taxes & fees
23 Bradley Circle @ Bradley Beach | Ocean-View Deck | Private Heated Pool | Sleeps 20
22 Hickory Cove
Palmetto Dunes Tennis and Pickleball Center - 10 minute walk
Dunes House on the Beach - 15 minute walk
Comfortable Living Room
Exceptional
(109 reviews)

Villa; 5 minute walk to Palmetto Dunes Beach with a Great Golf Course View!!

Hilton Head Island

7% off
S$2,611
for 7 nights, 1 villa
S$373 per night
includes taxes & fees
Villa; 5 minute walk to Palmetto Dunes Beach with a Great Golf Course View!!
Living area
Private kitchen
Dining
Harbour Town
Exceptional
(37 reviews)

Private Sea Pines Home w Large Deck. Great for couples!

Hilton Head Island

7% off
S$3,007
for 7 nights, 1 home
S$430 per night
includes taxes & fees
Private Sea Pines Home w Large Deck. Great for couples!
Private kitchen
Beautiful view of ocean just steps away.Very close to pool as well
Living area
Living area
Wonderful
(117 reviews)

AUGUST 18-20... 25-27 AVAILABLE FROM $99 nt. + tx/fees...3 night Min

Hilton Head Island

8% off
S$1,180
for 7 nights, 1 villa
S$169 per night
includes taxes & fees
AUGUST 18-20... 25-27 AVAILABLE FROM $99 nt. + tx/fees...3 night Min
Elevator nearby
Enjoy sunrise right at balcony
Admirals Row Building is right on the beach
Living room and kitchen
Excellent
(171 reviews)

Admirals Row 306: True Direct Oceanfront W/Panoramic Oceanview

Hilton Head Island

8% off
S$2,337
for 7 nights, 1 villa
S$334 per night
includes taxes & fees
Admirals Row 306: True Direct Oceanfront W/Panoramic Oceanview
Master bedroom
Living room
Kitchen
Pool
Exceptional
(77 reviews)

Renovated Harbourtown Villa with Lagoon View

Hilton Head Island

8% off
S$2,651
for 7 nights, 1 villa
S$379 per night
includes taxes & fees
Renovated Harbourtown Villa with Lagoon View
Living area
Exterior
Oceanside Resort and Huge Oceanside Pool and Restaurant/Bar!
View from front door. The kitchen is to the right.
Exceptional
(48 reviews)

Oceanside Resort- 5 Min Walk to Beach-2 Bed 2 Bath-Beach Chairs&Wagon-1st Floor

Hilton Head Island

7% off
S$2,173
for 7 nights, 1 villa
S$310 per night
includes taxes & fees
Oceanside Resort- 5 Min Walk to Beach-2 Bed 2 Bath-Beach Chairs&Wagon-1st Floor
Our balcony ocean front views
View from private balcony
Pool area for private complex .
Lifeguards on the beach during season with chair and umbrella rentals
Exceptional
(86 reviews)

# 314 DIRECT OCEANFRONT VILLA LOCATED IN NORTH FOREST BEACH AREA

Hilton Head Island

7% off
S$2,200
for 7 nights, 1 villa
S$314 per night
includes taxes & fees
# 314 DIRECT OCEANFRONT VILLA LOCATED IN NORTH FOREST BEACH AREA
The perfect place to relax!
Hilton Head Island - Shelter Cove Harbour & Marina
Relax in a light-filled living space with sliding glass doors opening to the first floor deck overlooking the course.
The kitchen is fully equipped for quick meals or family dinners, while the dining area provides views of the course!
Very good
(5 reviews)

2366 Racquet Club @ Sea Pines | Direct Golf View | Pet Friendly | Pool & Lagoon | Golf | Tennis

Hilton Head Island

5% off
S$2,377
for 7 nights, 1 apartment
S$340 per night
includes taxes & fees
2366 Racquet Club @ Sea Pines | Direct Golf View | Pet Friendly | Pool & Lagoon | Golf | Tennis
Dining
Pool
Property grounds
Room
Exceptional
(80 reviews)

Sunrise on the ocean - Best beach & pool view-Villamare

Hilton Head Island

15% off
S$4,646
for 7 nights, 1 apartment
S$664 per night
includes taxes & fees
Sunrise on the ocean - Best beach & pool view-Villamare
Living Room at 2388 Lighthouse Tennis Villas
Free access to the Sea Pines Beach Club a short bike ride away!
Lagoon Views from 2388 Lighthouse Tennis Villas
Harbour Town!
Exceptional
(104 reviews)

Center of Sea Pines; View of Lagoon; Walkable to Harbour Town/Beach Club/Market

Hilton Head Island

7% off
S$2,694
for 7 nights, 1 apartment
S$385 per night
includes taxes & fees
Center of Sea Pines; View of Lagoon; Walkable to Harbour Town/Beach Club/Market
Dining
Children’s area
Property grounds
Exterior detail
Exceptional
(68 reviews)

OCEANFRONT VILLA AMAZING VIEW. # 363

Hilton Head Island

7% off
S$1,571
for 7 nights, 1 villa
S$224 per night
includes taxes & fees
OCEANFRONT VILLA AMAZING VIEW. # 363
Private kitchen
What a beautiful way to celebrate a special day!
A glass of wine anyone?
Exterior
Exceptional
(139 reviews)

OCEANFRONT CONDO! Looking for a spring or summer get-away, you found it!

Hilton Head Island

7% off
S$2,291
for 7 nights, 1 apartment
S$327 per night
includes taxes & fees
OCEANFRONT CONDO! Looking for a spring or summer get-away, you found it!
Private kitchen
Dining
Living area
Pool
Exceptional
(15 reviews)

Beautiful Condo TheSpa Resort w/Indoor Outdoor Pools Hot Tub Tennis Water Front!

Hilton Head Island

7% off
S$1,450
for 7 nights, 1 apartment
S$207 per night
includes taxes & fees
Beautiful Condo TheSpa Resort w/Indoor Outdoor Pools Hot Tub Tennis Water Front!
Room
Living area
Exterior
Pool
Exceptional
(58 reviews)

Oceanfront Bliss: 2BR/3rd Floor Condo with Pool & Beach Access in Palmetto Dunes

Hilton Head Island

7% off
S$2,793
for 7 nights, 1 apartment
S$399 per night
includes taxes & fees
Oceanfront Bliss: 2BR/3rd Floor Condo with Pool & Beach Access in Palmetto Dunes
Bedroom 1 with Ensuite, First Floor:  Comfortable King-Size Bed, Smart TV and Lagoon views
Step into a world of contemporary elegance as you enter this newly renovated haven. The interior has been thoughtfully redesigned in 2024, boasting a seamless blend of modern amenities and classic charm.
Relax and unwind in the stylish living area, featuring plush furnishings and panoramic views of the lush landscape beyond.
Hilton Head Island - Shelter Cove Harbour & Marina
Exceptional
(5 reviews)

49 Night Heron @ Sea Pines | Lagoon Front Retreat | Walk to Beach | Golf & Tennis

Hilton Head Island

5% off
S$3,957
for 7 nights, 1 home
S$565 per night
includes taxes & fees
49 Night Heron @ Sea Pines | Lagoon Front Retreat | Walk to Beach | Golf & Tennis
Wonderful living and dining and kitchen area! Ceiling fan and great views!
What in incredible view!
Wonderful pool area to play or relax!
Sea Sides beach walk.
Exceptional
(100 reviews)

Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380

Hilton Head Island

7% off
S$1,474
for 7 nights, 1 home
S$211 per night
includes taxes & fees
Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380
Samsung TV / Hargray Platinum Cable Channels and Secure WIFI
Our Pool also has a shaded awning area if your getting too much sun
Kitchen and Living area with end unit side window....Light and Bright
FRONT ROW Ocean Villa....close to Pool, Beach Bar and Boardwalk to the Beach
Exceptional
(132 reviews)

Ocean Front 1st Row ~ Private Corner Unit ~ Close to Pool, Beach Bar & Boardwalk

Hilton Head Island

7% off
S$2,130
for 7 nights, 1 apartment
S$304 per night
includes taxes & fees
Ocean Front 1st Row ~ Private Corner Unit ~ Close to Pool, Beach Bar & Boardwalk
Interior
Pool
Interior
Living area
Exceptional
(124 reviews)

Beach Front with Ocean View

Hilton Head Island

7% off
S$1,287
for 7 nights, 1 apartment
S$184 per night
includes taxes & fees
Beach Front with Ocean View
Dining Table with seating for 6
Hilton Head Island - Shelter Cove Harbour & Marina
New plush New furnishings
Immerse yourself in oceanfront relaxation with family-friendly amenities, including a zero-entry heated pool, kiddie pool, and spa available YEAR-AROUND!
Exceptional
(14 reviews)

138 Shorewood @ Forest Beach | Steps to Beach | Year-Around Heated Pools & Spa

Hilton Head Island

5% off
S$2,718
for 7 nights, 1 apartment
S$388 per night
includes taxes & fees
138 Shorewood @ Forest Beach | Steps to Beach | Year-Around Heated Pools & Spa
Wonderful open area, all new paint!
A View from our Sundeck!
A View of our own Sundeck!
Room
Exceptional
(79 reviews)

RENOVATED! Seaside Villas 1 BDRM, 1 BA, 2 Free Bikes! Great Ocean Views! #129

Hilton Head Island

7% off
S$1,467
for 7 nights, 1 apartment
S$210 per night
includes taxes & fees
RENOVATED! Seaside Villas 1 BDRM, 1 BA, 2 Free Bikes! Great Ocean Views! #129
Open bedroom!
Wonderful sundeck!
Very nicely appointed!
Great place to get some sun!
Exceptional
(92 reviews)

Awesome Condo! King size bed! Updated! Ocean Views! 2 Bikes! #218 Great Reviews!

Hilton Head Island

7% off
S$1,509
for 7 nights, 1 apartment
S$216 per night
includes taxes & fees
Awesome Condo! King size bed! Updated! Ocean Views! 2 Bikes! #218 Great Reviews!
View from living room balcony straight ahead and to the right a little.
Walkway and beach carpet leading to beach
Kitchen area with full size washer and dryer
Interior
Exceptional
(98 reviews)

Ocean One 519, Top Floor, Direct Ocean View!

Hilton Head Island

6% off
S$2,051
for 7 nights, 1 apartment
S$293 per night
includes taxes & fees
Ocean One 519, Top Floor, Direct Ocean View!
Treetops has 3 onsite pools that are open April 1 - November 1
Spend time strolling around the Costal Discovery Museum
Welcome to "Our Happy Place"!
Take the stairs up to the 3rd bedroom and full bathroom
Exceptional
(109 reviews)

Dog Friendly ~ Walk to the beach ~ Screened in porch ~ 3 pools ~ New Appliances!

Hilton Head Island

7% off
S$3,199
for 7 nights, 1 villa
S$457 per night
includes taxes & fees
Dog Friendly ~ Walk to the beach ~ Screened in porch ~ 3 pools ~ New Appliances!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Take in the waterfront beauty of Hilton Head Island

The island views and other outdoor surroundings create an inviting atmosphere in Hilton Head Island. This city's golfing, cycling and bird watching draw many visitors. Tybee Island Beach and Marine Corps Recruit Depot Parris Island are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Hilton Head Island

Are you searching for attractions to see in the area? Travellers enjoy Hilton Head Island for its golfing, cycling and bird watching. Venture out of your holiday home and experience everything that makes Hilton Head Island a fun place to get away to. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Heron Point by Pete Dye at Sea Pines Resort (0.3 mi / 0.5 km)
  • Shipyard Golf Course (0.9 mi / 1.5 km)
  • Palmetto Dunes Club (2.5 mi / 4.1 km)
  • The Golf Courses of Palmetto Dunes (2.5 mi / 4.1 km)
  • Atlantic Dunes by Davis Love III (2.6 mi / 4.1 km)
  • Robert Trent Jones Oceanfront Course (2.7 mi / 4.4 km)

Exploring the beaches and other natural features in Hilton Head Island

Travellers enjoy Hilton Head Island for its island views, seaside and sunrises. Whether you're an active traveller or just want to spend some time taking in the scenery, Hilton Head Island is a great spot to appreciate mother nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Tybee Island Beach (11.3 mi / 18.1 km)
  • Sea Pines Forest Preserve (0.8 mi / 1.3 km)
  • Coligny Beach (1.4 mi / 2.2 km)
  • Palmetto Dunes Beach (2.9 mi / 4.6 km)
  • South Beach (4.3 mi / 6.9 km)
  • Singleton Beach (4.3 mi / 6.9 km)

Seasonal weather averages in Hilton Head Island

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 27°C.

Travelling to and around Hilton Head Island

The nearest airport is in Hilton Head Island, SC (HHH), located 6.1 mi (9.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Savannah - Hilton Head International Airport (SAV), which is 26.3 mi (42.3 km) away.

Frequently asked questions

What is the best area to stay in Hilton Head Island when booking a holiday rental?
If you're planning a holiday in Hilton Head Island, Folly Field is one of the most sought-after destinations to stay. No matter your travel style, Vrbo is sure to have a holiday rental here that's right for you.
What is the most popular type of holiday rental accommodation in Hilton Head Island?
The most desirable types of holiday rentals in Hilton Head Island are condos. After something a little different? Vrbo has a variety of options to match our guests' requirements, so you'll see properties in lots of sizes and shapes. The perfect fit is waiting for you — snap up yours today.
How much does it cost to rent a holiday rental in Hilton Head Island?
A number of things can influence the price of a holiday rental in Hilton Head Island, like the time of year, property type and length of stay. But, all Vrbo homes have one thing in common — excellent value. Simply add your travel dates to find your perfect match.
How much does it cost to rent a beach house in Hilton Head Island?
The average price for a holiday home by the beach in Hilton Head Island depends on when you'll be there and the size and type of property you're searching for. You can easily and quickly find prices on Vrbo by entering the dates you'll be travelling. Then use the handy filter tool to choose the number of bedrooms and amenities essential to you, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday rentals in Hilton Head Island?
Pack a suitcase for the pooch in your life because Hilton Head Island has 4,312 properties that roll out the welcome mat to doggie guests. Let your happy hound join in on the family trip at one of our pet-friendly holiday rentals on Vrbo. Simply enter your dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Hilton Head Island?
Tick the "pool" box in our filter tool and choose from 4,001 houses with private pools in Hilton Head Island on Vrbo. Morning dip, sunset soak or midnight swim? How you spend your leisure time is up to you when your holiday home has its own pool.
What are popular rental amenities in Hilton Head Island?
Some of the most popular rental amenities people are looking for in Hilton Head Island include tennis, nearby museums and a water view. Whether you're travelling with family, buddies or even pets, Vrbo holiday properties provide the best amenities for chilling out with your loved ones.
Are there large group holiday rentals in Hilton Head Island?
Pick from 784 holiday homes in Hilton Head Island that can host a group of 10 or more people. Whether you're organising time away with the family or a celebration like a birthday, there's enough room to get your favourite people together under one roof.
Are there holiday rentals in Hilton Head Island that welcome kids?
Hilton Head Island has 4,307 family-friendly holiday rentals to pick from. And tracking down a stay that welcomes kiddos is simple with our "Properties good for families" filter. On top of having the whole place to yourselves, you'll have access to perks and conveniences like dining rooms, full kitchens and yards.
What are the top attractions for families in Hilton Head Island?
Keep your kids busy at these awesome family-friendly attractions in Hilton Head Island:
  • Coligny Beach
  • The Sandbox
  • Singleton Beach
Are there one-bedroom holiday rentals in Hilton Head Island?
Yes, you can choose from 602 one-bedroom rentals in Hilton Head Island. Whether you want a cosy chalet or a fancy condo, our one-bedroom rentals are great if you don't require tons of space. One of the perks of having your own place? You won't ever have to share your holiday with strangers.
Can I find two-bedroom holiday rentals in Hilton Head Island?
Gather your nearest and dearest and enjoy a relaxing escape in one of the 1,847 two-bedroom holiday properties Hilton Head Island has to offer.
Are there holiday rentals with WiFi in Hilton Head Island?
Whether you'd like to keep up with world events, look over emails or surf social media, there are 1,622 holiday homes with WiFi in Hilton Head Island. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find holiday rentals with air conditioning in Hilton Head Island?
You'll have your pick of 4,121 Vrbo holiday homes with air conditioning in Hilton Head Island giving you that cooling breeze and extra element of comfort. Simply enter your preferred travel dates and then use our filter tool to locate properties with air conditioning.
How old do you have to be to rent a holiday rental in Hilton Head Island?
The minimum age is typically 16, 18 or 21. It can vary between properties on Vrbo, so look at the rules of your preferred Hilton Head Island stay before booking your escape.
How long can I rent a holiday rental in Hilton Head Island for?
The amount of time you can stay in a Hilton Head Island holiday rental for depends on each property. Simply put in your travel dates to browse available options offering extended stays. They include everything you need to make your extended trip more enjoyable and comfortable, like kitchens and air conditioning. Some Vrbo holiday rentals may also offer weekly or monthly discounted prices, so you can hang around longer for less.

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