Hilton Head Island holiday rentals

We found 10,349 holiday rentals — enter your dates for availability
Select from 1015 houses, 42 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:13 Nov - 20 Nov

Exterior
Dining
Living area
Private kitchen
Wonderful
(88 reviews)

South Beach Dog-friendly Waterfront Villa

Hilton Head Island

8% off
S$3,613
for 7 nights, 1 villa
S$516 per night
includes taxes & fees
South Beach Dog-friendly Waterfront Villa
Location: Sea Pines Resort, South Beach, Hilton Head Island.
Welcome to 23 South Beach Lane!
Hilton Head Island - Shelter Cove Harbour & Marina
Eat-in kitchen table for 6, kitchen bar with additional 5 seats
Exceptional
(11 reviews)

23 South Beach Lane @ Sea Pines | Steps to Beach | Pool & Spa | Pickleball

Hilton Head Island

6% off
S$9,523
for 7 nights, 1 home
S$1,360 per night
includes taxes & fees
23 South Beach Lane @ Sea Pines | Steps to Beach | Pool & Spa | Pickleball
Private kitchen
Dining
Interior
Basking in the warmth of a sun-kissed day, our private pool is a haven of joy.
Exceptional
(63 reviews)

Private Pool, Hot Tub & Beach Days in Palmetto Dunes.

Hilton Head Island

7% off
S$9,198
for 7 nights, 1 home
S$1,314 per night
includes taxes & fees
Private Pool, Hot Tub & Beach Days in Palmetto Dunes.
Upstairs, the spacious loft provides a versatile and inviting space
Hilton Head Island - Shelter Cove Harbour & Marina
Carolina Room can be accessed via the deck or Master bedroom
Unwind in the inviting indoor-outdoor living space, complete with brand-new modern furnishings, a cozy fireplace
Exceptional
(7 reviews)

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

Hilton Head Island

5% off
S$6,102
for 7 nights, 1 home
S$872 per night
includes taxes & fees
18 Swing About @ Palmetto Dunes | Private Pool | Gorgeous Golf views
Comfortable Living Room
Palmetto Dunes Tennis and Pickleball Center - 10 minute walk
Fully Equipped Kitchen
Dunes House on the Beach - 15 minute walk
Exceptional
(106 reviews)

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

Hilton Head Island

7% off
S$2,802
for 7 nights, 1 villa
S$400 per night
includes taxes & fees
Villa; 5 minute walk to Palmetto Dunes Beach with a Great Golf Course View!!
Cozy, inviting seating ideal for quality time with family and friends
Elegant windows with views of the outdoors
Hilton Head Island - Shelter Cove Harbour & Marina
Second level has a loft kitchenette area with access to the balcony
Exceptional
(6 reviews)

20 Knotts Way @ North Forest Beach | Luxury Retreat | Steps from the Beach | Loaded with Amenities

Hilton Head Island

5% off
S$10,865
for 7 nights, 1 home
S$1,552 per night
includes taxes & fees
20 Knotts Way @ North Forest Beach | Luxury Retreat | Steps from the Beach | Loaded with Amenities
Kitchen
Beach Club! Great food, beach access, live music all within a easy 10 min walk
Our unit is across the street from 
Atlantic Dunes by Davis Love III
Atlantic Dunes by Davis Love III
Exceptional
(22 reviews)

Beautiful Lagoon/Golf Views! Short Walk/Bike Ride to Beach Club

Hilton Head Island

7% off
S$3,235
for 7 nights, 1 villa
S$462 per night
includes taxes & fees
Beautiful Lagoon/Golf Views! Short Walk/Bike Ride to Beach Club
Living area
Beautiful view of ocean just steps away.Very close to pool as well
SUNDOWN AT THE BREAKERS
Private kitchen
Wonderful
(116 reviews)

$AVE BIG! Aug dates from just $129 Sep- Oct from just $129...! +Tax and Fees

Hilton Head Island

8% off
S$1,228
for 7 nights, 1 villa
S$175 per night
includes taxes & fees
$AVE BIG! Aug dates from just $129 Sep- Oct from just $129...! +Tax and Fees
The perfect place to relax!
Hilton Head Island - Shelter Cove Harbour & Marina
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.
Very good
(5 reviews)

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

Hilton Head Island

5% off
S$2,059
for 7 nights, 1 apartment
S$294 per night
includes taxes & fees
2366 Racquet Club @ Sea Pines | Direct Golf View | Pet Friendly | Pool & Lagoon | Golf | Tennis
Living room and kitchen
Enjoy sunrise right at balcony
Admirals Row Building is right on the beach
Elevator nearby
Excellent
(171 reviews)

Admirals Row 306: True Direct Oceanfront W/Panoramic Oceanview

Hilton Head Island

8% off
S$2,350
for 7 nights, 1 villa
S$336 per night
includes taxes & fees
Admirals Row 306: True Direct Oceanfront W/Panoramic Oceanview
Private kitchen
Pool
Living area
Living area
Exceptional
(66 reviews)

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

Hilton Head Island

7% off
S$1,855
for 7 nights, 1 villa
S$265 per night
includes taxes & fees
FULLY RENOVATED, 5-MINUTE WALK TO BEACH - 2 POOLS - 4 Pickleball +Tennis Courts
Your pool and kiddy pool in a great setting
The Harbour Town Lighthouse is iconic!
Boardwalk to the Beach!
Another Aerial View of The Breakers
Exceptional
(44 reviews)

Perfect Hilton Head Island Beach Getaway! “Newly Renovated”

Hilton Head Island

8% off
S$2,545
for 7 nights, 1 apartment
S$364 per night
includes taxes & fees
Perfect Hilton Head Island Beach Getaway! “Newly Renovated”
Interior
Private kitchen
Living area
Exterior
Exceptional
(12 reviews)

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

Hilton Head Island

5% off
S$2,103
for 7 nights, 1 villa
S$300 per night
includes taxes & fees
Luxe 2BR/2.5BA Marsh View Villa Near Harbour Town - Stoney Splash - 260 Stoney Creek Road
Property grounds
Beachwalk Villa Unit Deck View
Villa Front Entrance - Beachwalk Shipyard
NEW KITCHEN in 2023
Exceptional
(99 reviews)

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

Hilton Head Island

11% off
S$2,221
for 7 nights, 1 home
S$317 per night
includes taxes & fees
194 Beachwalk Villa,OWNER Mgmt,BEACH LOCKER,Steps to Beach,Family/Pet Friendly
View from patio
Living room
Master bedroom
Kitchen
Exceptional
(75 reviews)

Renovated Harbourtown Villa with Lagoon View

Hilton Head Island

7% off
S$2,726
for 7 nights, 1 villa
S$389 per night
includes taxes & fees
Renovated Harbourtown Villa with Lagoon View
The pirates ship at Celebration Park
Fireworks at Shelter Cove
Lots of dining and shopping at Shelter Cove
2.4 mile drive to Shelter cove harbor
Exceptional
(74 reviews)

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

Hilton Head Island

7% off
S$1,943
for 7 nights, 1 villa
S$278 per night
includes taxes & fees
GREAT OCEAN VIEW to Relax, Rest, and Restore on Beautiful Hilton Head Island🌴🌺☀️
Dining
Looking from Entry through the Villa
King Comfort
Kiddie Pool on a quiet Evening
Exceptional
(61 reviews)

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

Hilton Head Island

7% off
S$2,147
for 7 nights, 1 villa
S$307 per night
includes taxes & fees
Oceanside Resort! King Master Suite, Sleeps 6, Walk to the Beach!
Room
Living area
Interior
Living area
Exceptional
(24 reviews)

Coastal Calm Retreat: Hilton Head Island 2b/2b Villa

Hilton Head Island

7% off
S$1,494
for 7 nights, 1 villa
S$213 per night
includes taxes & fees
Coastal Calm Retreat: Hilton Head Island 2b/2b Villa
A glass of wine anyone?
What a beautiful way to celebrate a special day!
Private kitchen
Exterior
Exceptional
(137 reviews)

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

Hilton Head Island

7% off
S$2,233
for 7 nights, 1 apartment
S$319 per night
includes taxes & fees
OCEANFRONT CONDO! Looking for a spring or summer get-away, you found it!
Indoor pool, spas, sauna, fitness center and track offer yearround amenities.
The beach in front of Hilton Head Resort is beautiful with much less traffic.
Private kitchen
Living area
Exceptional
(104 reviews)

FIRE SALE 25% OFF August Hltn Head Resrt 2BR/2BA: GLF/MRSH/OCEN VIEW. BEST BEACH

Hilton Head Island

8% off
S$1,734
for 7 nights, 1 apartment
S$248 per night
includes taxes & fees
FIRE SALE 25% OFF August Hltn Head Resrt 2BR/2BA: GLF/MRSH/OCEN VIEW. BEST BEACH
Property grounds
Children’s area
Exterior detail
Private kitchen
Exceptional
(66 reviews)

OCEANFRONT VILLA AMAZING VIEW. # 363

Hilton Head Island

7% off
S$1,558
for 7 nights, 1 villa
S$223 per night
includes taxes & fees
OCEANFRONT VILLA AMAZING VIEW. # 363
Ample dining space
Plenty of relaxing outdoor space
Cook
Enjoy the water
Exceptional
(12 reviews)

Family-oriented lagoon-side home in Sea Pines close to Harbour Town

Hilton Head Island

15% off
S$3,206
for 7 nights, 1 home
S$458 per night
includes taxes & fees
Family-oriented lagoon-side home in Sea Pines close to Harbour Town
Private kitchen
Interior
Dining
Dining
Exceptional
(73 reviews)

3 BEDROOM LUXURY HOME PET FRIENDLY. 1-2 MINUTE WALK TO THE BEACH

Hilton Head Island

8% off
S$5,405
for 7 nights, 1 home
S$772 per night
includes taxes & fees
3 BEDROOM LUXURY HOME PET FRIENDLY. 1-2 MINUTE WALK TO THE BEACH
Private kitchen
Living area
Dining
Pool
Exceptional
(109 reviews)

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

Hilton Head Island

8% off
S$2,201
for 7 nights, 1 apartment
S$314 per night
includes taxes & fees
Fabulously Updated 2-Bedroom, 2-Bathroom Condo With Beach Access
  • 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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