Hilton Head Island holiday rentals

We found 10,363 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:20 Nov - 27 Nov

SUNDOWN AT THE BREAKERS
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$1,236
for 7 nights, 1 villa
S$177 per night
includes taxes & fees
AUGUST 18-20... 25-27 AVAILABLE FROM $99 nt. + tx/fees...3 night Min
Oceanside Resort and Huge Oceanside Pool and Restaurant/Bar!
Exterior
View from front door. The kitchen is to the right.
Living area
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$2,209
for 7 nights, 1 villa
S$316 per night
includes taxes & fees
Oceanside Resort- 5 Min Walk to Beach-2 Bed 2 Bath-Beach Chairs&Wagon-1st Floor
Villa Front Entrance - Beachwalk Shipyard
Beachwalk Villa Unit Deck View
Dinning for 6
NEW KITCHEN in 2023
Exceptional
(100 reviews)

194 Beachwalk Villa,OWNER Mgmt,BEACH LOCKER,Steps to Beach,Family/Pet Friendly

Hilton Head Island

11% off
S$2,453
for 7 nights, 1 home
S$350 per night
includes taxes & fees
194 Beachwalk Villa,OWNER Mgmt,BEACH LOCKER,Steps to Beach,Family/Pet Friendly
Living area
Marina
Marina
Pool
Exceptional
(42 reviews)

Great for Families! Lg Pool, Near Harbour Town, Beach, Golf, Tennis & Pickleball

Hilton Head Island

7% off
S$3,933
for 7 nights, 1 villa
S$562 per night
includes taxes & fees
Great for Families! Lg Pool, Near Harbour Town, Beach, Golf, Tennis & Pickleball
View from patio
Living room
Kitchen
Master bedroom
Exceptional
(76 reviews)

Renovated Harbourtown Villa with Lagoon View

Hilton Head Island

7% off
S$2,712
for 7 nights, 1 villa
S$387 per night
includes taxes & fees
Renovated Harbourtown Villa with Lagoon View
Dining
Looking from Entry through the Villa
Kiddie Pool on a quiet Evening
King Comfort
Exceptional
(61 reviews)

Oceanside Resort! King Master Suite, Sleeps 6, Walk to the Beach!

Hilton Head Island

7% off
S$2,166
for 7 nights, 1 villa
S$309 per night
includes taxes & fees
Oceanside Resort! King Master Suite, Sleeps 6, Walk to the Beach!
Dining
Balcony
Pool
Private kitchen
Exceptional
(123 reviews)

Spectacular Oceanfront, Top Floor, 1 BR, 1 BA, steps from the beach!

Hilton Head Island

8% off
S$2,296
for 7 nights, 1 apartment
S$328 per night
includes taxes & fees
Spectacular Oceanfront, Top Floor, 1 BR, 1 BA, steps from the beach!
Dining
Children’s area
Property grounds
Private kitchen
Exceptional
(66 reviews)

OCEANFRONT VILLA AMAZING VIEW. # 363

Hilton Head Island

7% off
S$1,568
for 7 nights, 1 villa
S$224 per night
includes taxes & fees
OCEANFRONT VILLA AMAZING VIEW. # 363
Dining
Pool
Property grounds
Room
Exceptional
(80 reviews)

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

Hilton Head Island

15% off
S$4,729
for 7 nights, 1 apartment
S$676 per night
includes taxes & fees
Sunrise on the ocean - Best beach & pool view-Villamare
Property grounds
Pool
Private kitchen
Property grounds
Exceptional
(230 reviews)

Perfect Beach & Pool View, Fun, Updated Interior, Great Location - Breakers 226

Hilton Head Island

8% off
S$1,618
for 7 nights, 1 villa
S$231 per night
includes taxes & fees
Perfect Beach & Pool View, Fun, Updated Interior, Great Location - Breakers 226
Immerse yourself in oceanfront relaxation with family-friendly amenities, including a zero-entry heated pool, kiddie pool, and spa available YEAR-AROUND!
Hilton Head Island - Shelter Cove Harbour & Marina
New plush New furnishings
Pickleball and Tennis at Sea Pines
Exceptional
(14 reviews)

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

Hilton Head Island

6% off
S$3,303
for 7 nights, 1 apartment
S$472 per night
includes taxes & fees
138 Shorewood @ Forest Beach | Steps to Beach | Year-Around Heated Pools & Spa
Indoor pool open year round!
Swing on property, edge of beach.
Ensuite primary bedroom
55 inch TV
Exceptional
(24 reviews)

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

Hilton Head Island

8% off
S$1,780
for 7 nights, 1 villa
S$254 per night
includes taxes & fees
Peaceful HHI Escape! Private Beach Access, in/outdoor pools, hot tub, sauna!
Pool
Living area
Private kitchen
Exterior
Exceptional
(109 reviews)

Fabulously Updated 2-Bedroom, 2-Bathroom Condo With Beach Access

Hilton Head Island

7% off
S$2,244
for 7 nights, 1 apartment
S$321 per night
includes taxes & fees
Fabulously Updated 2-Bedroom, 2-Bathroom Condo With Beach Access
Living area
Private kitchen
Property grounds
Room
Exceptional
(39 reviews)

Comfy Island House Villa - Just a Walk to the Beach & Coligny

Hilton Head Island

13% off
S$2,137
for 7 nights, 1 villa
S$305 per night
includes taxes & fees
Comfy Island House Villa - Just a Walk to the Beach & Coligny
Larger heated pool with Jacuzzi
Living area
Interior
Living area
Exceptional
(135 reviews)

Family Oriented - 2 Bdm 2 Bth, TV's, WiFi, Balcony, Poolside, Club House, Beach

Hilton Head Island

7% off
S$1,425
for 7 nights, 1 villa
S$204 per night
includes taxes & fees
Family Oriented - 2 Bdm 2 Bth, TV's, WiFi, Balcony, Poolside, Club House, Beach
Seaside Villa's
View to ocean from sundeck
View of balcony.
Celebration Park
Exceptional
(269 reviews)

SUPER NICE! New King Bed! Great Ocean View!1 BD ~ 1 BA, 2 Bikes! #136

Hilton Head Island

7% off
S$1,349
for 7 nights, 1 apartment
S$193 per night
includes taxes & fees
SUPER NICE! New King Bed! Great Ocean View!1 BD ~ 1 BA, 2 Bikes! #136
Kitchen
Building one outdoor pool
Master bedroom
dining area
Wonderful
(91 reviews)

Beach Resort, Walk to the Ocean, Free Secure Wi-Fi in Building 1

Hilton Head Island

6% off
S$1,502
for 7 nights, 1 apartment
S$215 per night
includes taxes & fees
Beach Resort, Walk to the Ocean, Free Secure Wi-Fi in Building 1
Room
A View from our Sundeck!
Wonderful open area, all new paint!
Welcome to Seaside Villas! An Ocean front Complex!
Exceptional
(78 reviews)

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

Hilton Head Island

7% off
S$1,491
for 7 nights, 1 apartment
S$213 per night
includes taxes & fees
RENOVATED! Seaside Villas 1 BDRM, 1 BA, 2 Free Bikes! Great Ocean Views! #129
View from the ocean of Sea Side Villas.
Wonderful sundeck!
Open bedroom!
Great place to get some sun!
Exceptional
(90 reviews)

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

Hilton Head Island

7% off
S$1,562
for 7 nights, 1 apartment
S$223 per night
includes taxes & fees
Awesome Condo! King size bed! Updated! Ocean Views! 2 Bikes! #218 Great Reviews!
Treetops & Ocean Breeze front Entrance
Spend time strolling around the Costal Discovery Museum
Take the stairs up to the 3rd bedroom and full bathroom
Welcome to "Our Happy Place"!
Exceptional
(109 reviews)

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

Hilton Head Island

7% off
S$3,261
for 7 nights, 1 villa
S$466 per night
includes taxes & fees
Dog Friendly ~ Walk to the beach ~ Screened in porch ~ 3 pools ~ New Appliances!
Beautiful kitchen area!
Hilton Head's famous SeaPines Harbour Town lighthouse!
Living area
Relaxing area on balcony with awesome views of the ocean!
Exceptional
(195 reviews)

Great Romantic Get-A-Way!! View of Ocean! HIGH QUALITY FINISHES! 2 BIKES!!

Hilton Head Island

7% off
S$1,710
for 7 nights, 1 apartment
S$244 per night
includes taxes & fees
Great Romantic Get-A-Way!! View of Ocean! HIGH QUALITY FINISHES! 2 BIKES!!
Private kitchen
Interior
Living area
Living area
Exceptional
(15 reviews)

"Nanas Haven" Family Friendly 2B2B, 1st floor end unit

Hilton Head Island

7% off
S$1,777
for 7 nights, 1 apartment
S$254 per night
includes taxes & fees
"Nanas Haven" Family Friendly 2B2B, 1st floor end unit
Property grounds
Harbourtown Lighthouse
Living room/kitchen.
Living area
Exceptional
(197 reviews)

AWESOME REMODEL! FREE BIKES, ALL BEACH GEAR, on the beach, 5-star reviews.

Hilton Head Island

7% off
S$2,062
for 7 nights, 1 apartment
S$295 per night
includes taxes & fees
AWESOME REMODEL! FREE BIKES, ALL BEACH GEAR, on the beach, 5-star reviews.
Living area
Indoor pool and hot tub
Room
Living area
Exceptional
(40 reviews)

Walk to beach, updated 2/2 condo sleeps 6, in & outdoor pools, tennis, courtyard

Hilton Head Island

6% off
S$2,053
for 7 nights, 1 apartment
S$293 per night
includes taxes & fees
Walk to beach, updated 2/2 condo sleeps 6, in & outdoor pools, tennis, courtyard
  • 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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