Hilton Head Island holiday rentals

We found 10,365 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

Private kitchen
Dining
Terrace/patio
Exterior
Wonderful
(88 reviews)

South Beach Dog-friendly Waterfront Villa

Hilton Head Island

8% off
S$3,617
for 7 nights, 1 villa
S$517 per night
includes taxes & fees
South Beach Dog-friendly Waterfront Villa
Room
Living area
Pool
Private kitchen
Exceptional
(89 reviews)

AMAZING views! Full DIRECT Oceanfront Villa! Totally renovated!

Hilton Head Island

8% off
S$3,718
for 7 nights, 1 villa
S$531 per night
includes taxes & fees
AMAZING views! Full DIRECT Oceanfront Villa! Totally renovated!
Unwind in the inviting indoor-outdoor living space, complete with brand-new modern furnishings, a cozy fireplace
Hilton Head Island - Shelter Cove Harbour & Marina
Carolina Room can be accessed via the deck or Master bedroom
Retreat to our stunning 18 Swing About, nestled in Palmetto Dunes Resort, where up to 12 guests (and your furry friend) can unwind in style.
Exceptional
(7 reviews)

18 Swing About @ Palmetto Dunes | Private Pool | Gorgeous Golf views

Hilton Head Island

6% off
S$7,703
for 7 nights, 1 home
S$1,100 per night
includes taxes & fees
18 Swing About @ Palmetto Dunes | Private Pool | Gorgeous Golf views
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$1,220
for 7 nights, 1 villa
S$174 per night
includes taxes & fees
AUGUST 18-20... 25-27 AVAILABLE FROM $99 nt. + tx/fees...3 night Min
Living area
Coco's on the Beach at end of boardwalk.
Living area
Building 3/Atrium - wi-fi lounge.
Exceptional
(94 reviews)

7-Day Discounts in 3BR Villa at Hilton Head Resort!

Hilton Head Island

8% off
S$3,626
for 7 nights, 1 villa
S$518 per night
includes taxes & fees
7-Day Discounts in 3BR Villa at Hilton Head Resort!
Open bedroom
Enjoy sunrise right at balcony
Elevator nearby
Living room and kitchen
Excellent
(171 reviews)

Admirals Row 306: True Direct Oceanfront W/Panoramic Oceanview

Hilton Head Island

8% off
S$2,195
for 7 nights, 1 villa
S$314 per night
includes taxes & fees
Admirals Row 306: True Direct Oceanfront W/Panoramic Oceanview
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$1,842
for 7 nights, 1 villa
S$263 per night
includes taxes & fees
FULLY RENOVATED, 5-MINUTE WALK TO BEACH - 2 POOLS - 4 Pickleball +Tennis Courts
Pool
Marina
Outdoor dining
Living area
Exceptional
(42 reviews)

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

Hilton Head Island

7% off
S$3,857
for 7 nights, 1 villa
S$551 per night
includes taxes & fees
Great for Families! Lg Pool, Near Harbour Town, Beach, Golf, Tennis & Pickleball
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

8% off
S$3,011
for 7 nights, 1 villa
S$430 per night
includes taxes & fees
# 314 DIRECT OCEANFRONT VILLA LOCATED IN NORTH FOREST BEACH AREA
View from patio
Living room
Master bedroom
Pool
Exceptional
(76 reviews)

Renovated Harbourtown Villa with Lagoon View

Hilton Head Island

8% off
S$2,647
for 7 nights, 1 villa
S$378 per night
includes taxes & fees
Renovated Harbourtown Villa with Lagoon View
Dining
Private kitchen
Outdoor dining
Living area
Exceptional
(37 reviews)

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

Hilton Head Island

7% off
S$2,801
for 7 nights, 1 home
S$400 per night
includes taxes & fees
Private Sea Pines Home w Large Deck. Great for couples!
Jamaica Joe's beach bar right in boardwalk and next to pool
Fireworks at Shelter Cove
The pirates ship at Celebration Park
Lots of dining and shopping at Shelter Cove
Exceptional
(74 reviews)

GREAT OCEAN VIEW to Relax, Rest, and Restore on Beautiful Hilton Head Island🌴🌺☀️

Hilton Head Island

7% off
S$1,929
for 7 nights, 1 villa
S$276 per night
includes taxes & fees
GREAT OCEAN VIEW to Relax, Rest, and Restore on Beautiful Hilton Head Island🌴🌺☀️
Private kitchen
What a beautiful way to celebrate a special day!
Private kitchen
A glass of wine anyone?
Exceptional
(137 reviews)

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

Hilton Head Island

7% off
S$2,217
for 7 nights, 1 apartment
S$317 per night
includes taxes & fees
OCEANFRONT CONDO! Looking for a spring or summer get-away, you found it!
Private kitchen
Balcony
Pool
Dining
Exceptional
(123 reviews)

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

Hilton Head Island

8% off
S$2,259
for 7 nights, 1 apartment
S$323 per night
includes taxes & fees
Spectacular Oceanfront, Top Floor, 1 BR, 1 BA, steps from the beach!
Less than a 5 min walk to the brand new Low Country Celebration Park
Brand new kids' playground at Low Country Celebration Park - go explore!
Living area with new sleeper sofa
Entry area with storage for shoes, jackets, beach towels, bike helmets, etc.
Exceptional
(139 reviews)

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

Hilton Head Island

8% off
S$1,690
for 7 nights, 1 villa
S$241 per night
includes taxes & fees
Book now for Fall 2026! Short walk to park/playground & Beach, near Coligny
Kitchen at 2388 Lighthouse Tennis Villas
Free access to the Sea Pines Beach Club a short bike ride away!
Living Room at 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$2,529
for 7 nights, 1 apartment
S$361 per night
includes taxes & fees
Center of Sea Pines; View of Lagoon; Walkable to Harbour Town/Beach Club/Market
Dining Table with seating for 6
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$3,237
for 7 nights, 1 apartment
S$462 per night
includes taxes & fees
138 Shorewood @ Forest Beach | Steps to Beach | Year-Around Heated Pools & Spa
Exterior
Living area
Pool
Private kitchen
Exceptional
(109 reviews)

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

Hilton Head Island

8% off
S$2,185
for 7 nights, 1 apartment
S$312 per night
includes taxes & fees
Fabulously Updated 2-Bedroom, 2-Bathroom Condo With Beach Access
Indoor pool open year round!
Swing on property, edge of beach.
Ensuite primary bedroom
Garden walk to beach.
Exceptional
(25 reviews)

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

Hilton Head Island

8% off
S$1,749
for 7 nights, 1 villa
S$250 per night
includes taxes & fees
Peaceful HHI Escape! Private Beach Access, in/outdoor pools, hot tub, sauna!
Dining Room and Living Room
Tennis Courts
Living Room
Picnic/Grilling Area
Exceptional
(58 reviews)

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

Hilton Head Island

7% off
S$1,574
for 7 nights, 1 villa
S$225 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!
Wonderful pool area to play or relax!
Wonderful living and dining and kitchen area! Ceiling fan and great views!
Exceptional
(100 reviews)

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

Hilton Head Island

7% off
S$1,620
for 7 nights, 1 home
S$231 per night
includes taxes & fees
Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380
Room
Living area
Living area
Pool
Exceptional
(61 reviews)

SeaCrest ~N Forest Beach Coligny OCEANVIEW~HUGE 1 bedroom! Top floor! POOL! Gym

Hilton Head Island

7% off
S$3,021
for 7 nights, 1 apartment
S$432 per night
includes taxes & fees
SeaCrest ~N Forest Beach Coligny OCEANVIEW~HUGE 1 bedroom! Top floor! POOL! Gym
dining area
Building one outdoor pool
Living room
Master bedroom
Wonderful
(91 reviews)

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

Hilton Head Island

6% off
S$1,475
for 7 nights, 1 apartment
S$211 per night
includes taxes & fees
Beach Resort, Walk to the Ocean, Free Secure Wi-Fi in Building 1
Welcome to Seaside Villas! An Ocean front Complex!
A View from our Sundeck!
Room
Wonderful open area, all new paint!
Exceptional
(78 reviews)

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

Hilton Head Island

7% off
S$1,464
for 7 nights, 1 apartment
S$209 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. 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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