Hilton Head Island holiday rentals

We found 10,367 holiday rentals — enter your dates for availability
Select from 1026 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:4 Dec - 11 Dec

Living area
Dining
Exterior
Private kitchen
Wonderful
(89 reviews)

South Beach Dog-friendly Waterfront Villa

Hilton Head Island

8% off
S$3,530
for 7 nights, 1 villa
S$504 per night
includes taxes & fees
South Beach Dog-friendly Waterfront Villa
Kitchen. Two of every appliance.
Back of the house. Pool and spa (heated for a fee).
Grand stairway. Great for family photos.
1st floor living room. Plenty of room!
Exceptional
(105 reviews)

V. Large House with Pool/Elevator/Fire pit in Palmetto Dunes-2 min walk to beach

Hilton Head Island

27% off
S$16,747
for 7 nights, 1 home
S$2,392 per night
includes taxes & fees
V. Large House with Pool/Elevator/Fire pit in Palmetto Dunes-2 min walk to beach
Living room view looking toward kitchen.
Living room featuring gorgeous wall of windows
Bartender's view toward the pool
View of home from the beach. We are dead center in this photo.
Exceptional
(65 reviews)

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

Hilton Head Island

8% off
S$8,725
for 7 nights, 1 home
S$1,246 per night
includes taxes & fees
2nd Row luxury home with pool, tiki bar, private beach boardwalk- 30 Knotts Way
Jamaica Joez beach bar is located right next to the oceanfront pool
Our private oceanfront pool
Ottoman hold extra bedding and pillows for sofa bed functioning  as coffee table
Coconutz Sports Bar, on site
Exceptional
(46 reviews)

BEAUTIFUL REMODELED VILLA JUST STEPS TO THE OCEAN

Hilton Head Island

7% off
S$1,676
for 7 nights, 1 villa
S$239 per night
includes taxes & fees
BEAUTIFUL REMODELED VILLA JUST STEPS TO THE OCEAN
Room
Living area
Private kitchen
Interior
Exceptional
(91 reviews)

AMAZING views! Full DIRECT Oceanfront Villa! Totally renovated!

Hilton Head Island

8% off
S$3,732
for 7 nights, 1 villa
S$533 per night
includes taxes & fees
AMAZING views! Full DIRECT Oceanfront Villa! Totally renovated!
Harbour Town
Private kitchen
Outdoor dining
Dining
Exceptional
(37 reviews)

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

Hilton Head Island

7% off
S$2,710
for 7 nights, 1 home
S$387 per night
includes taxes & fees
Private Sea Pines Home w Large Deck. Great for couples!
Foyer - Bed/Bath on each side
Palmetto Dunes Private Beach (gated community) just a 90 second walk from villa
Living Area
Owner's suite
Exceptional
(172 reviews)

Completely Renovated Top Floor Villa Steps To Beach

Hilton Head Island

12% off
S$1,648
for 7 nights, 1 villa
S$235 per night
includes taxes & fees
Completely Renovated Top Floor Villa Steps To Beach
Pool
Living room
Master bedroom
View from patio
Exceptional
(77 reviews)

Renovated Harbourtown Villa with Lagoon View

Hilton Head Island

8% off
S$2,657
for 7 nights, 1 villa
S$380 per night
includes taxes & fees
Renovated Harbourtown Villa with Lagoon View
Aerial View of Property (from street side)
Main Living Area - Large Picture Window with Unobstructed Ocean View
Newly Renovated Dining Area - facing Kitchen and Entry
Newly Renovated Dining Area - facing Ocean
Exceptional
(66 reviews)

5 Star Rating / Direct Oceanfront / Sweeping Views / Steps from Beach

Hilton Head Island

7% off
S$2,243
for 7 nights, 1 villa
S$320 per night
includes taxes & fees
5 Star Rating / Direct Oceanfront / Sweeping Views / Steps from Beach
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$2,170
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
Living area
Coco's on the Beach at end of boardwalk.
Building 3/Atrium - wi-fi lounge.
Living area
Exceptional
(95 reviews)

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

Hilton Head Island

8% off
S$3,640
for 7 nights, 1 villa
S$520 per night
includes taxes & fees
7-Day Discounts in 3BR Villa at Hilton Head Resort!
HOST & HOME presents…34 Heath Drive! Step inside to this beautifully renovated 4-bedroom retreat in the prestigious gated community of Palmetto Dunes!
Fully equipped kitchen with an island for your culinary exploits
A beautiful open floor plan to connect the kitchen and living room spaces!
Relax on the large, comfortable sectional after a day of exploring
Exceptional
(7 reviews)

34 Heath Drive @ Palmetto Dunes | Balcony Overlooking Pool | Bunk Room | Prime Location

Hilton Head Island

5% off
S$5,220
for 7 nights, 1 home
S$746 per night
includes taxes & fees
34 Heath Drive @ Palmetto Dunes | Balcony Overlooking Pool | Bunk Room | Prime Location
Interior
Sea Pines beach club
Living area
Harbour Town marina
Exceptional
(33 reviews)

Lovely Villa in Sea Pines, 2-Min Walk to Beach, Marina, Pool, Braddock Cove View

Hilton Head Island

7% off
S$2,209
for 7 nights, 1 apartment
S$316 per night
includes taxes & fees
Lovely Villa in Sea Pines, 2-Min Walk to Beach, Marina, Pool, Braddock Cove View
Harbour Town!
Free access to the Sea Pines Beach Club a short bike ride away!
Kitchen at 2388 Lighthouse Tennis Villas
Living Room at 2388 Lighthouse Tennis Villas
Exceptional
(104 reviews)

Center of Sea Pines; View of Lagoon; Walkable to Harbour Town/Beach Club/Market

Hilton Head Island

7% off
S$2,510
for 7 nights, 1 apartment
S$359 per night
includes taxes & fees
Center of Sea Pines; View of Lagoon; Walkable to Harbour Town/Beach Club/Market
Relax in a light-filled living space with sliding glass doors opening to the first floor deck overlooking the course.
The perfect place to relax!
The kitchen is fully equipped for quick meals or family dinners, while the dining area provides views of the course!
Hilton Head Island renowned Golf Courses
Very good
(5 reviews)

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

Hilton Head Island

5% off
S$2,027
for 7 nights, 1 apartment
S$290 per night
includes taxes & fees
2366 Racquet Club @ Sea Pines | Direct Golf View | Pet Friendly | Pool & Lagoon | Golf | Tennis
Room
Living area
Private kitchen
plenty of seating at ocean side pool!  Heated year-round.
Exceptional
(149 reviews)

138 BREAKERS, Direct Oceanfront - Best Rates and GREAT Reviews! Rent from Owner

Hilton Head Island

7% off
S$1,453
for 7 nights, 1 villa
S$208 per night
includes taxes & fees
138 BREAKERS, Direct Oceanfront - Best Rates and GREAT Reviews! Rent from Owner
Full kitchen with granite counters & tiled backsplash
One of three Hilton Head Resort pools located right below our villa
Robert Trent Jones golf course - Palmetto Dunes - adjacent to Hilton Head Resort
Living Area
Exceptional
(106 reviews)

Stunning Ocean & Tidal Creek Views -- Best Resort Vantage Point!

Hilton Head Island

7% off
S$1,784
for 7 nights, 1 apartment
S$255 per night
includes taxes & fees
Stunning Ocean & Tidal Creek Views -- Best Resort Vantage Point!
Wonderful pool area to play or relax!
What in incredible view!
Sea Sides beach walk.
Great kitchen area with dishwasher!
Exceptional
(100 reviews)

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

Hilton Head Island

7% off
S$1,477
for 7 nights, 1 home
S$211 per night
includes taxes & fees
Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380
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!
Entry area with storage for shoes, jackets, beach towels, bike helmets, etc.
Front view of condo - ground level
Exceptional
(139 reviews)

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

Hilton Head Island

8% off
S$1,696
for 7 nights, 1 villa
S$242 per night
includes taxes & fees
Book now for Fall 2026! Short walk to park/playground & Beach, near Coligny
Living Room
Pool
Exterior
Gym
Exceptional
(44 reviews)

Villamare Beachfront 2-bedroom condo minutes from Palmetto Dunes Club

Hilton Head Island

7% off
S$3,062
for 7 nights, 1 apartment
S$437 per night
includes taxes & fees
Villamare Beachfront 2-bedroom condo minutes from Palmetto Dunes Club
View from the condo of pool and ocean!
New Furniture in living room ! Open and bright!
Extra chairs!
Condo has tile floors, dining for 6, lots of seating in living room!
Exceptional
(37 reviews)

Beach Front~2 BDRM Condo, 2 BA, Pool, 4 Bikes & VIEWS! One Level! #1F

Hilton Head Island

7% off
S$1,766
for 7 nights, 1 apartment
S$252 per night
includes taxes & fees
Beach Front~2 BDRM Condo, 2 BA, Pool, 4 Bikes & VIEWS! One Level! #1F
Marina
Property grounds
Dining
Room
Very good
(13 reviews)

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

Hilton Head Island

7% off
S$1,550
for 7 nights, 1 apartment
S$221 per night
includes taxes & fees
Spacious Condo w/Indoor Pool, Hot Tub, Tennis, Pickball Walk to Beach& Coligny!
Open bedroom!
Wonderful sundeck!
View from the ocean of Sea Side Villas.
Great place to get some sun!
Exceptional
(92 reviews)

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

Hilton Head Island

7% off
S$1,477
for 7 nights, 1 apartment
S$211 per night
includes taxes & fees
Awesome Condo! King size bed! Updated! Ocean Views! 2 Bikes! #218 Great Reviews!
Dining
Balcony
Pool
Private kitchen
Exceptional
(124 reviews)

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

Hilton Head Island

8% off
S$2,268
for 7 nights, 1 apartment
S$324 per night
includes taxes & fees
Spectacular Oceanfront, Top Floor, 1 BR, 1 BA, steps from the beach!
  • 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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