Hilton Head Island holiday rentals

We found 10,180 holiday rentals — enter your dates for availability
Select from 986 houses, 26 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:8 Jan - 15 Jan

Kitchen
South Beach Marina just a few yards away
Washer and dryer
View from the entrance door
Exceptional
(222 reviews)

Updated Villa. Close To Beach, Salty Dog. And South Beach Marina

Hilton Head Island

7% off
S$1,384
for 7 nights, 1 villa
S$198 per night
includes taxes & fees
Updated Villa. Close To Beach, Salty Dog. And South Beach Marina
Dunes House on the Beach - 15 minute walk
Palmetto Dunes Tennis and Pickleball Center - 10 minute walk
22 Hickory Cove
Comfortable Living Room
Exceptional
(109 reviews)

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

Hilton Head Island

7% off
S$2,168
for 7 nights, 1 villa
S$310 per night
includes taxes & fees
Villa; 5 minute walk to Palmetto Dunes Beach with a Great Golf Course View!!
Sandy path to the big water takes you leisurely through the dunes.
View from the balcony, just steps from the beach boardwalk. Unit is the 5th in.
Fountain in front of the unit, alongside the boardwalk. A pretty bonus.
Boardwalk to the beach is only steps away!
Exceptional
(86 reviews)

Ocean View, Pool, Tennis, Pickleball, Seasonal Music

Hilton Head Island

7% off
S$1,506
for 7 nights, 1 apartment
S$215 per night
includes taxes & fees
Ocean View, Pool, Tennis, Pickleball, Seasonal Music
Queen bed with storage drawers
Pool
Hallway looking down to living room at the entrance of the villa
Oceanside Bar & Grille
Exceptional
(217 reviews)

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

Hilton Head Island

7% off
S$1,405
for 7 nights, 1 villa
S$201 per night
includes taxes & fees
Ocean view - Beautiful Penthouse Condo - Large heated pools & Hot Tubs!
Living area
Exterior
Living area
View from front door. The kitchen is to the right.
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$2,172
for 7 nights, 1 villa
S$310 per night
includes taxes & fees
Oceanside Resort- 5 Min Walk to Beach-2 Bed 2 Bath-Beach Chairs&Wagon-1st Floor
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
(9 reviews)

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

Hilton Head Island

6% off
S$4,915
for 7 nights, 1 home
S$702 per night
includes taxes & fees
Renovated Sea Pines Home w/ Golf Views | Kegerator, Hot Tub, Sleeps 12, Pet-Friendly
Living area
Sun Rise to 8 miles south Tybee,GA what a view!!! Direct Oceanfront!
Fully equipped kitchen.Dishwasher,full-size stove,ice-maker & dining table four.
Queen sleeper sofa
Exceptional
(162 reviews)

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

Hilton Head Island

7% off
S$2,127
for 7 nights, 1 apartment
S$304 per night
includes taxes & fees
Direct Oceanfront Luxury, Miles of Ocean View, King bed, Walk-in Shower.
Property grounds
Pool
Living area
Private kitchen
Exceptional
(233 reviews)

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

Hilton Head Island

8% off
S$1,572
for 7 nights, 1 villa
S$225 per night
includes taxes & fees
Perfect Beach & Pool View, Fun, Updated Interior, Great Location - Breakers 226
Beach
Pool
Dining
Living area
Exceptional
(11 reviews)

55 Steps To The Beach - 2nd Row Ocean - Private Pool

Hilton Head Island

6% off
S$8,835
for 7 nights, 1 home
S$1,262 per night
includes taxes & fees
55 Steps To The Beach - 2nd Row Ocean - Private Pool
Living Room w/ Sleep Sofa
Back Deck with lagoon view
Pool - 30 seconds from our Villa
Kitchen
Exceptional
(39 reviews)

Beach, Tennis & Golf Escape - Free Tennis

Hilton Head Island

8% off
S$2,534
for 7 nights, 1 villa
S$362 per night
includes taxes & fees
Beach, Tennis & Golf Escape - Free Tennis
Hilton Head Island Beach & Tennis .  Our Villa is located in center "Y" building
Our private oceanfront pool
Jamaica Joez beach bar is located right next to the oceanfront pool
Coconutz Sports Bar, on site
Exceptional
(47 reviews)

BEAUTIFUL REMODELED VILLA, STEPS TO THE OCEAN - STR Permit #073298

Hilton Head Island

7% off
S$1,686
for 7 nights, 1 villa
S$241 per night
includes taxes & fees
BEAUTIFUL REMODELED VILLA, STEPS TO THE OCEAN - STR Permit #073298
Living area
Beautiful view of ocean just steps away.Very close to pool as well
Living area
SUNDOWN AT THE BREAKERS
Wonderful
(119 reviews)

$89!...GREAT OCTOBER DATES AVAILABLE FROM JUST $89 FRI/SAT JUST $129...+tx/fees

Hilton Head Island

10% off
S$1,185
for 7 nights, 1 villa
S$169 per night
includes taxes & fees
$89!...GREAT OCTOBER DATES AVAILABLE FROM JUST $89 FRI/SAT JUST $129...+tx/fees
Dining
Looking from Entry through the Villa
Kiddie Pool on a quiet Evening
Living area
Exceptional
(61 reviews)

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

Hilton Head Island

7% off
S$1,942
for 7 nights, 1 villa
S$277 per night
includes taxes & fees
Oceanside Resort! King Master Suite, Sleeps 6, Walk to the Beach!
Bar (on property)
Outdoor dining
Exterior
Pool
Exceptional
(157 reviews)

AMAZING OCEAN VIEW with PRIVATE BEACH ACCESS !!!

Hilton Head Island

7% off
S$1,562
for 7 nights, 1 apartment
S$223 per night
includes taxes & fees
AMAZING OCEAN VIEW with PRIVATE BEACH ACCESS !!!
Designer touches throughout this luxury home.
Living area
3 story, 6 BR / 6 BA Luxury Custom Home
upscale appliances including  6 burner Wolf range.
Wonderful
(55 reviews)

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

Hilton Head Island

7% off
S$7,628
for 7 nights, 1 home
S$1,090 per night
includes taxes & fees
Singleton Beach 6B/6B Sleeps 18. Pool. Walk or FREE shuttle to best BEACH on HHI
Pool
Private kitchen
Living area
Dining
Exceptional
(16 reviews)

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

Hilton Head Island

6% off
S$2,112
for 7 nights, 1 villa
S$302 per night
includes taxes & fees
Luxe 2BR/2.5BA Marsh View Villa Near Harbour Town - Stoney Splash - 260 Stoney Creek Road
Step into a world of contemporary elegance as you enter this newly renovated haven.
This house features an open floor plan to easily gather your group
Dive into shimmering pool waters and spent lazy days soaking the sun on the tanning ledge
Enjoy dining right by the pool!
Exceptional
(14 reviews)

Pet Friendly 3BR, 3 Baths Next to Sea Pines Forest Preserve, Heated Pool

Hilton Head Island

5% off
S$4,054
for 7 nights, 1 home
S$579 per night
includes taxes & fees
Pet Friendly 3BR, 3 Baths Next to Sea Pines Forest Preserve, Heated Pool
Queen sleeper with memory foam mattress
View from Our Balcony
(Zoom applied)
Entrance/Front Hall
Kitchen Area
Exceptional
(118 reviews)

Oceanview Condo - overlooking pool and 100 yards to beach

Hilton Head Island

10% off
S$1,275
for 7 nights, 1 apartment
S$182 per night
includes taxes & fees
Oceanview Condo - overlooking pool and 100 yards to beach
A nice large smart TV with games and books in the cabinet
Beach Club! Great food, beach access, live music all within a easy 10 min walk
Kitchen
Our unit is across the street from 
Atlantic Dunes by Davis Love III
Exceptional
(27 reviews)

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

Hilton Head Island

7% off
S$2,389
for 7 nights, 1 villa
S$341 per night
includes taxes & fees
Beautiful Lagoon/Golf Views! Short Walk/Bike Ride to Beach Club
Private kitchen
Dining
Exterior
Living area
Wonderful
(91 reviews)

South Beach Dog-friendly Waterfront Villa

Hilton Head Island

8% off
S$3,628
for 7 nights, 1 villa
S$518 per night
includes taxes & fees
South Beach Dog-friendly Waterfront Villa
Outdoor dining
Palmetto Dunes Golf Courses
Shelter Cove Tuesday Night Fireworks
Living area
Exceptional
(192 reviews)

Beach Lover's Retreat End Unit Villa House w Pet-Private Beach

Hilton Head Island

7% off
S$1,623
for 7 nights, 1 villa
S$232 per night
includes taxes & fees
Beach Lover's Retreat End Unit Villa House w Pet-Private Beach
Balcony View - Spring - Beach Bar, Pool and Ocean
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
FRONT ROW Ocean Villa....close to Pool, Beach Bar and Boardwalk to the Beach
Exceptional
(135 reviews)

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

Hilton Head Island

7% off
S$2,035
for 7 nights, 1 apartment
S$291 per night
includes taxes & fees
Ocean Front 1st Row ~ Private Corner Unit ~ Close to Pool, Beach Bar & Boardwalk
Sleeper sofa in main room - with flat screen TV. Breakfast bar with granite top.
The beach in front of Hilton Head Resort is beautiful with much less traffic.
Indoor pool, spas, sauna, fitness center and track offer yearround amenities.
Living area
Exceptional
(106 reviews)

GREAT VALUE Hilton Head Resrt 2BR 2BA: GULF MARSH OCEAN VIEW. BEST BEACH

Hilton Head Island

8% off
S$1,531
for 7 nights, 1 apartment
S$219 per night
includes taxes & fees
GREAT VALUE Hilton Head Resrt 2BR 2BA: GULF MARSH OCEAN VIEW. BEST BEACH
Kitchen
Living room
View from patio
Pool
Exceptional
(77 reviews)

Renovated Harbourtown Villa with Lagoon View

Hilton Head Island

7% off
S$2,539
for 7 nights, 1 villa
S$363 per night
includes taxes & fees
Renovated Harbourtown Villa with Lagoon View
  • 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. 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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