Hilton Head Island holiday rentals

We found 10,329 holiday rentals — enter your dates for availability
Select from 1012 houses, 28 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:18 Dec - 25 Dec

Terrace/patio
Dining
Private kitchen
Living area
Wonderful
(91 reviews)

South Beach Dog-friendly Waterfront Villa

Hilton Head Island

8% off
S$4,023
for 7 nights, 1 villa
S$575 per night
includes taxes & fees
South Beach Dog-friendly Waterfront Villa
Pool
Sea Pines Beach Club
Harbor Town
Sea Pines Beach Club
Exceptional
(121 reviews)

Celebrate at the Beach Thanksgiving! Private Pool and Free Bikes!

Hilton Head Island

7% off
S$4,291
for 7 nights, 1 home
S$613 per night
includes taxes & fees
Celebrate at the Beach Thanksgiving! Private Pool and Free Bikes!
Hilton Head Island renowned Golf Courses
Relax in a light-filled living space with sliding glass doors opening to the first floor deck overlooking the course.
Just a bike ride to Harbour Town
The perfect place to relax!
Very good
(5 reviews)

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

Hilton Head Island

5% off
S$2,010
for 7 nights, 1 apartment
S$287 per night
includes taxes & fees
2366 Racquet Club @ Sea Pines | Direct Golf View | Pool & Lagoon | Golf | Tennis
Bar eating area
Large balcony with lots of seating!
View from our covered balcony.  Perfect sunrise view!
Kitchen eating area
Exceptional
(90 reviews)

449 CAPTAINS WALK -OCEANFRONT Condo with DIRECT POOL and OCEAN VIEWS!

Hilton Head Island

7% off
S$3,654
for 7 nights, 1 villa
S$522 per night
includes taxes & fees
449 CAPTAINS WALK -OCEANFRONT Condo with DIRECT POOL and OCEAN VIEWS!
Coconutz Sports Bar, on site
Our private oceanfront pool
Jamaica Joez beach bar is located right next to the oceanfront pool
Ottoman hold extra bedding and pillows for sofa bed functioning  as coffee table
Exceptional
(47 reviews)

BEAUTIFUL REMODELED VILLA JUST STEPS TO THE OCEAN

Hilton Head Island

7% off
S$1,647
for 7 nights, 1 villa
S$235 per night
includes taxes & fees
BEAUTIFUL REMODELED VILLA JUST STEPS TO THE OCEAN
Newly Renovated Dining Area - facing Ocean
Main Living Area - Large Picture Window with Unobstructed Ocean View
Newly Renovated Dining Area - facing Kitchen and Entry
Pool Deck Area
Exceptional
(67 reviews)

Direct Oceanfront / Sweeping Views / Steps from Beach

Hilton Head Island

7% off
S$2,670
for 7 nights, 1 villa
S$381 per night
includes taxes & fees
Direct Oceanfront / Sweeping Views / Steps from Beach
View from front door. The kitchen is to the right.
Exterior
Living area
Oceanside Resort and Huge Oceanside Pool and Restaurant/Bar!
Exceptional
(49 reviews)

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

Hilton Head Island

7% off
S$2,099
for 7 nights, 1 villa
S$300 per night
includes taxes & fees
Oceanside Resort- 5 Min Walk to Beach-2 Bed 2 Bath-Beach Chairs&Wagon-1st Floor
Pool
Private kitchen
Living area
Dining
Exceptional
(15 reviews)

Luxe 2BR/2.5BA Marsh View Villa Near Harbour Town - Stoney Splash - 260 Stoney Creek Road

Hilton Head Island

6% off
S$2,124
for 7 nights, 1 villa
S$303 per night
includes taxes & fees
Luxe 2BR/2.5BA Marsh View Villa Near Harbour Town - Stoney Splash - 260 Stoney Creek Road
Expansive patio with open golf views, multiple seating areas, and heated spa.
Welcome to Pin High Palms — renovated, spacious, and designed for gathering
Private hot tub surrounded by tropical landscaping — the perfect place to unwind after the beach or golf
Dining area ideal for shared meals and conversation
Exceptional
(7 reviews)

Renovated Sea Pines Home w/ Golf Views | Kegerator, Hot Tub, Sleeps 12, Pet-Friendly

Hilton Head Island

6% off
S$4,387
for 7 nights, 1 home
S$627 per night
includes taxes & fees
Renovated Sea Pines Home w/ Golf Views | Kegerator, Hot Tub, Sleeps 12, Pet-Friendly
Owner's suite
Palmetto Dunes Private Beach (gated community) just a 90 second walk from villa
Community Pool
Foyer - Bed/Bath on each side
Exceptional
(172 reviews)

Completely Renovated Top Floor Villa Steps To Beach

Hilton Head Island

13% off
S$1,592
for 7 nights, 1 villa
S$227 per night
includes taxes & fees
Completely Renovated Top Floor Villa Steps To Beach
Living area
Pool
Property grounds
Living area
Exceptional
(67 reviews)

FULLY RENOVATED, 5-MINUTE WALK TO BEACH - 2 POOLS - 4 Pickleball & Tennis Courts

Hilton Head Island

7% off
S$1,811
for 7 nights, 1 villa
S$259 per night
includes taxes & fees
FULLY RENOVATED, 5-MINUTE WALK TO BEACH - 2 POOLS - 4 Pickleball & Tennis Courts
Living area
Private kitchen
Outdoor dining
Harbour Town
Exceptional
(37 reviews)

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

Hilton Head Island

7% off
S$2,820
for 7 nights, 1 home
S$403 per night
includes taxes & fees
Private Sea Pines Home w Large Deck. Great for couples!
NEW remodel + upgrades primary bathroom with walk-in tile shower & stone floor
Enjoy the view & sounds of Atlantic Ocean from your private balcony
Coastal charm meets modern comfort in this bright, beachy living room + kitchen
Remoded primary bedroom with NEW Queen size bed. Whisper quiet fan + SMART TV
Exceptional
(121 reviews)

Beachfront & Oceanview - Steps to Beach/Pool/Coligny-Renovated Couples Getaway

Hilton Head Island

7% off
S$1,955
for 7 nights, 1 villa
S$279 per night
includes taxes & fees
Beachfront & Oceanview - Steps to Beach/Pool/Coligny-Renovated Couples Getaway
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
Balcony View - Spring - Beach Bar, Pool and Ocean
Exceptional
(134 reviews)

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

Hilton Head Island

8% off
S$2,355
for 7 nights, 1 apartment
S$336 per night
includes taxes & fees
Ocean Front 1st Row ~ Private Corner Unit ~ Close to Pool, Beach Bar & Boardwalk
Room
Pool
Property grounds
Dining
Exceptional
(82 reviews)

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

Hilton Head Island

16% off
S$4,499
for 7 nights, 1 apartment
S$643 per night
includes taxes & fees
Sunrise on the ocean - Best beach & pool view-Villamare
Entry area with storage for shoes, jackets, beach towels, bike helmets, etc.
Brand new kids' playground at Low Country Celebration Park - go explore!
Living area with new sleeper sofa
Less than a 5 min walk to the brand new Low Country Celebration Park
Exceptional
(140 reviews)

Book now for Fall 2026! Short walk to park/playground & Beach, near Coligny

Hilton Head Island

8% off
S$1,661
for 7 nights, 1 villa
S$237 per night
includes taxes & fees
Book now for Fall 2026! Short walk to park/playground & Beach, near Coligny
Exterior
Living area
Pool
Beach
Exceptional
(59 reviews)

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

Hilton Head Island

7% off
S$2,235
for 7 nights, 1 apartment
S$319 per night
includes taxes & fees
Oceanfront Bliss: 2BR/3rd Floor Condo with Pool & Beach Access in Palmetto Dunes
Living area
Sun Rise to 8 miles south Tybee,GA what a view!!! Direct Oceanfront!
Queen sleeper sofa
King size Memory foam mattress.
Exceptional
(161 reviews)

Direct Oceanfront Luxury, Miles of Ocean View, King bed, Walk-in Shower.

Hilton Head Island

8% off
S$2,148
for 7 nights, 1 apartment
S$307 per night
includes taxes & fees
Direct Oceanfront Luxury, Miles of Ocean View, King bed, Walk-in Shower.
Living Room
Tennis Courts
Pool
Dining Room and Living Room
Wonderful
(59 reviews)

Beautiful, Hilton Head Island 2BR/2BA Villa.. 100 Yards from the Atlantic Ocean!

Hilton Head Island

7% off
S$1,549
for 7 nights, 1 villa
S$221 per night
includes taxes & fees
Beautiful, Hilton Head Island 2BR/2BA Villa.. 100 Yards from the Atlantic Ocean!
Great kitchen area with dishwasher!
What in incredible view!
Sea Sides beach walk.
Wonderful pool area to play or relax!
Exceptional
(103 reviews)

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

Hilton Head Island

7% off
S$1,427
for 7 nights, 1 home
S$204 per night
includes taxes & fees
Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380
Queen bed with storage drawers
Pool
Game and internet room as part of amenities on site
Private kitchen
Exceptional
(214 reviews)

Ocean view - Beautiful Penthouse Condo - Large heated pools & Hot Tubs!

Hilton Head Island

7% off
S$1,569
for 7 nights, 1 villa
S$224 per night
includes taxes & fees
Ocean view - Beautiful Penthouse Condo - Large heated pools & Hot Tubs!
Indoor pool open year round!
Swing on property, edge of beach.
Garden walk to beach.
Ensuite primary bedroom
Exceptional
(29 reviews)

Peaceful HHI Escape! Private Beach Access, in/outdoor pools, hot tub, sauna!

Hilton Head Island

8% off
S$1,651
for 7 nights, 1 villa
S$236 per night
includes taxes & fees
Peaceful HHI Escape! Private Beach Access, in/outdoor pools, hot tub, sauna!
Children’s area
Marina
Interior
Living area
Wonderful
(10 reviews)

Walk to Beach & Coligny -Indoor / Outdoor Pool / Hot Tub / Tennis Pickleball!

Hilton Head Island

8% off
S$2,107
for 7 nights, 1 apartment
S$301 per night
includes taxes & fees
Walk to Beach & Coligny -Indoor / Outdoor Pool / Hot Tub / Tennis Pickleball!
Wonderful open area, all new paint!
A View from our Sundeck!
Room
Welcome to Seaside Villas! An Ocean front Complex!
Exceptional
(83 reviews)

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

Hilton Head Island

7% off
S$1,421
for 7 nights, 1 apartment
S$203 per night
includes taxes & fees
RENOVATED! Seaside Villas 1 BDRM, 1 BA, 2 Free Bikes! Great Ocean Views! #129
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    Enjoy full kitchens, laundry, pools, gardens and more
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    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. Marine Corps Recruit Depot Parris Island and River Street 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:

  • 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)
  • Burkes Beach (4.5 mi / 7.3 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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