Hilton Head Island holiday rentals

We found 10,316 holiday rentals — enter your dates for availability
Select from 1003 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:25 Dec - 1 Jan

View of home from the beach. We are dead center in this photo.
Living room featuring gorgeous wall of windows
Living room view looking toward kitchen.
Very large deck awaits with hot tub, heated pool, tiki bar (!), bbq grill etc.
Exceptional
(67 reviews)

2nd Row luxury home with pool, tiki bar, private beach boardwalk- 30 Knotts Way

Hilton Head Island

8% off
S$13,773
for 7 nights, 1 home
S$1,968 per night
includes taxes & fees
2nd Row luxury home with pool, tiki bar, private beach boardwalk- 30 Knotts Way
View from our covered balcony.  Perfect sunrise view!
Large balcony with lots of seating!
Bar eating area
View from balcony entrance into living room.
Exceptional
(90 reviews)

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

Hilton Head Island

7% off
S$3,524
for 7 nights, 1 villa
S$503 per night
includes taxes & fees
449 CAPTAINS WALK -OCEANFRONT Condo with DIRECT POOL and OCEAN VIEWS!
Living area
Beautiful view of ocean just steps away.Very close to pool as well
Living area
Private kitchen
Wonderful
(118 reviews)

GREAT SEP/OCT DATES AVAILABLE FROM JUST $109 BEST PRICES...$AVE...+ tx/ fees

Hilton Head Island

8% off
S$1,272
for 7 nights, 1 villa
S$182 per night
includes taxes & fees
GREAT SEP/OCT DATES AVAILABLE FROM JUST $109 BEST PRICES...$AVE...+ tx/ fees
Enjoy a unique layout with lavish amenities, multiple cozy decks, and porches.
Located near the historic Mitchellville section of Hilton Head Island, this hidden gem of a home is perfect for sunset strolls on a secluded beach, just a 10-minute walk away.
Kitchen has everything needed to cook and serve basic meals
This hidden gem comfortably accommodates up to 12 guests and your furry friend.
Exceptional
(9 reviews)

Fish Haul Beach | FREE Heated Pool | Walk to Private Beach | Pet-Friendly

Hilton Head Island

5% off
S$6,911
for 7 nights, 1 home
S$987 per night
includes taxes & fees
Fish Haul Beach | FREE Heated Pool | Walk to Private Beach | Pet-Friendly
Newly Renovated Dining Area - facing Ocean
Main Living Area - Large Picture Window with Unobstructed Ocean View
Pool Deck Area
Aerial View of Property (from street side)
Exceptional
(67 reviews)

Direct Oceanfront / Sweeping Views / Steps from Beach

Hilton Head Island

7% off
S$2,652
for 7 nights, 1 villa
S$379 per night
includes taxes & fees
Direct Oceanfront / Sweeping Views / Steps from Beach
Hilton Head Island Beach & Tennis .  Our Villa is located in center "Y" building
Our private oceanfront pool
Ottoman hold extra bedding and pillows for sofa bed functioning  as coffee table
Coconutz Sports Bar, on site
Exceptional
(47 reviews)

BEAUTIFUL REMODELED VILLA JUST STEPS TO THE OCEAN

Hilton Head Island

7% off
S$1,721
for 7 nights, 1 villa
S$246 per night
includes taxes & fees
BEAUTIFUL REMODELED VILLA JUST STEPS TO THE OCEAN
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$2,305
for 7 nights, 1 villa
S$329 per night
includes taxes & fees
Luxe 2BR/2.5BA Marsh View Villa Near Harbour Town - Stoney Splash - 260 Stoney Creek Road
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$2,105
for 7 nights, 1 villa
S$301 per night
includes taxes & fees
Oceanside Resort- 5 Min Walk to Beach-2 Bed 2 Bath-Beach Chairs&Wagon-1st Floor
3 story, 6 BR / 6 BA Luxury Custom Home
Living area
upscale appliances including  6 burner Wolf range.
Pool
Wonderful
(54 reviews)

Singleton Beach 6B/6B Sleeps 18. Pool. Walk or FREE shuttle to best BEACH on HHI

Hilton Head Island

8% off
S$6,547
for 7 nights, 1 home
S$935 per night
includes taxes & fees
Singleton Beach 6B/6B Sleeps 18. Pool. Walk or FREE shuttle to best BEACH on HHI
Living Room w/ Sleep Sofa
Back Deck with lagoon view
Kitchen
Front Entry
Exceptional
(39 reviews)

Beach, Tennis & Golf Escape - Free Tennis

Hilton Head Island

8% off
S$2,151
for 7 nights, 1 villa
S$307 per night
includes taxes & fees
Beach, Tennis & Golf Escape - Free Tennis
Pool
Living room
Kitchen
Master bedroom
Exceptional
(77 reviews)

Renovated Harbourtown Villa with Lagoon View

Hilton Head Island

8% off
S$2,619
for 7 nights, 1 villa
S$374 per night
includes taxes & fees
Renovated Harbourtown Villa with Lagoon View
Exterior
What a beautiful way to celebrate a special day!
Private kitchen
Private kitchen
Exceptional
(143 reviews)

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

Hilton Head Island

8% off
S$2,163
for 7 nights, 1 apartment
S$309 per night
includes taxes & fees
OCEANFRONT CONDO! Looking for a spring or summer get-away, you found it!
Exterior detail
Children’s area
Property grounds
Private kitchen
Exceptional
(71 reviews)

OCEANFRONT VILLA AMAZING VIEW. # 363

Hilton Head Island

7% off
S$1,552
for 7 nights, 1 villa
S$222 per night
includes taxes & fees
OCEANFRONT VILLA AMAZING VIEW. # 363
Indoor pool open year round!
Swing on property, edge of beach.
Ensuite primary bedroom
55 inch TV
Exceptional
(30 reviews)

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

Hilton Head Island

8% off
S$1,744
for 7 nights, 1 villa
S$249 per night
includes taxes & fees
Peaceful HHI Escape! Private Beach Access, in/outdoor pools, hot tub, sauna!
Interior
Pool
Private kitchen
Living area
Exceptional
(128 reviews)

Beach Front with Ocean View

Hilton Head Island

7% off
S$1,268
for 7 nights, 1 apartment
S$181 per night
includes taxes & fees
Beach Front with Ocean View
Property grounds
Pool
Private kitchen
Property grounds
Exceptional
(232 reviews)

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

Hilton Head Island

8% off
S$1,518
for 7 nights, 1 villa
S$217 per night
includes taxes & fees
Perfect Beach & Pool View, Fun, Updated Interior, Great Location - Breakers 226
Samsung TV / Hargray Platinum Cable Channels and Secure WIFI
Our Pool also has a shaded awning area if your getting too much sun
Balcony View - Spring - Beach Bar, Pool and Ocean
Kitchen and Living area with end unit side window....Light and Bright
Exceptional
(135 reviews)

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

Hilton Head Island

8% off
S$2,430
for 7 nights, 1 apartment
S$347 per night
includes taxes & fees
Ocean Front 1st Row ~ Private Corner Unit ~ Close to Pool, Beach Bar & Boardwalk
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$1,553
for 7 nights, 1 villa
S$222 per night
includes taxes & fees
Beautiful, Hilton Head Island 2BR/2BA Villa.. 100 Yards from the Atlantic Ocean!
Queen sleeper sofa
Sun Rise to 8 miles south Tybee,GA what a view!!! Direct Oceanfront!
Living area
King size Memory foam mattress.
Exceptional
(162 reviews)

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

Hilton Head Island

8% off
S$2,055
for 7 nights, 1 apartment
S$294 per night
includes taxes & fees
Direct Oceanfront Luxury, Miles of Ocean View, King bed, Walk-in Shower.
Savor your morning coffee or enjoy happy hour with loved ones on the covered patio, where a fresh marine breeze adds to the ambiance.
The fully-equipped kitchen, upgraded with granite countertops and stainless steel appliances, invites culinary adventures with local specialties.
After a day of exploring the island, unwind in a comfortable bed with the finest quality bedding, ensuring a restful night's sleep.
Modern stainless appliances
Excellent
(8 reviews)

7104 Harbourside 1 @ Shelter Cove | Pool | Stunning Marina Views

Hilton Head Island

5% off
S$2,204
for 7 nights, 1 apartment
S$315 per night
includes taxes & fees
7104 Harbourside 1 @ Shelter Cove | Pool | Stunning Marina Views
Ocean view right side of balcony
Pool
Private kitchen
Oceanside Bar & Grille
Exceptional
(215 reviews)

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

Hilton Head Island

7% off
S$1,697
for 7 nights, 1 villa
S$242 per night
includes taxes & fees
Ocean view - Beautiful Penthouse Condo - Large heated pools & Hot Tubs!
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$2,651
for 7 nights, 1 apartment
S$379 per night
includes taxes & fees
Walk to Beach & Coligny -Indoor / Outdoor Pool / Hot Tub / Tennis Pickleball!
Marina
Property grounds
Pool
Room
Very good
(14 reviews)

Spacious Condo w/Indoor Pool, Hot Tub, Tennis, Pickball Walk to Beach& Coligny!

Hilton Head Island

7% off
S$1,504
for 7 nights, 1 apartment
S$215 per night
includes taxes & fees
Spacious Condo w/Indoor Pool, Hot Tub, Tennis, Pickball Walk to Beach& Coligny!
Terrace/patio
Living area
Exterior detail
Property grounds
Excellent
(6 reviews)

Windward Village in Shipyard - Beautiful remodeled Condo overlook Pool Hot Tub !

Hilton Head Island

7% off
S$1,810
for 7 nights, 1 apartment
S$259 per night
includes taxes & fees
Windward Village in Shipyard - Beautiful remodeled Condo overlook Pool Hot Tub !
  • Peace of mind

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    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. 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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