Hilton Head Island holiday rentals

We found 10,167 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

Interior
Take the bike paths or short drive to Harbor Town Shopping and Restaurants!!
Fully Stocked Large Kitchen with plenty of cabinets and granite countertops
Living area
Exceptional
(184 reviews)

5th Row, Sea Pines-South Beach, Private Pool, Private Path to Beach, 4 EnSuites

Hilton Head Island

7% off
S$5,580
for 7 nights, 1 home
S$797 per night
includes taxes & fees
5th Row, Sea Pines-South Beach, Private Pool, Private Path to Beach, 4 EnSuites
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.
Hilton Head Island - Shelter Cove Harbour & Marina
Carolina Room can be accessed via the deck or Master bedroom
Upstairs, the spacious loft provides a versatile and inviting space
Exceptional
(7 reviews)

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

Hilton Head Island

5% off
S$6,067
for 7 nights, 1 home
S$867 per night
includes taxes & fees
18 Swing About @ Palmetto Dunes | Private Pool | Gorgeous Golf views
The spacious living room is designed for gatherings.
With views of the pool, making it a perfect spot for morning coffee or casual dining.
Hilton Head Island - Shelter Cove Harbour & Marina
Complete with ample comfortable seating and large bay windows that not only flood the space with light but also offer scenic views of the backyard.
Very good
(6 reviews)

24 Cartgate @ Palmetto Dunes | Pool & Spa | 10-min to Beach | Golf, Pickleball & Tennis

Hilton Head Island

5% off
S$5,935
for 7 nights, 1 home
S$848 per night
includes taxes & fees
24 Cartgate @ Palmetto Dunes | Pool & Spa | 10-min to Beach | Golf, Pickleball & Tennis
Kitchen
Beach Club! Great food, beach access, live music all within a easy 10 min walk
A nice large smart TV with games and books in the cabinet
Our unit is across the street from 
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$3,228
for 7 nights, 1 villa
S$461 per night
includes taxes & fees
Beautiful Lagoon/Golf Views! Short Walk/Bike Ride to Beach Club
Building 3/Atrium - wi-fi lounge.
Coco's on the Beach at end of boardwalk.
Entrance sign to resort at Highway 278.
Living area
Exceptional
(94 reviews)

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

Hilton Head Island

8% off
S$3,729
for 7 nights, 1 villa
S$533 per night
includes taxes & fees
7-Day Discounts in 3BR Villa at Hilton Head Resort!
Living room and kitchen
Enjoy sunrise right at balcony
Open bedroom
Elevator nearby
Excellent
(171 reviews)

Admirals Row 306: True Direct Oceanfront W/Panoramic Oceanview

Hilton Head Island

8% off
S$2,393
for 7 nights, 1 villa
S$342 per night
includes taxes & fees
Admirals Row 306: True Direct Oceanfront W/Panoramic Oceanview
HOST & HOME presents...11 Pender Lane! Nestled within the tranquil ambience of Sea Pines Resort.
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
Step into a world of contemporary elegance as you enter this newly renovated haven.
Exceptional
(10 reviews)

11 Pender Lane @ Sea Pines | Private Pool | Pet-Friendly | Golf & Tennis | Large Patio

Hilton Head Island

5% off
S$3,766
for 7 nights, 1 home
S$538 per night
includes taxes & fees
11 Pender Lane @ Sea Pines | Private Pool | Pet-Friendly | Golf & Tennis | Large Patio
King Comfort
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$2,170
for 7 nights, 1 villa
S$310 per night
includes taxes & fees
Oceanside Resort! King Master Suite, Sleeps 6, Walk to the Beach!
Private kitchen
Children’s area
Dining
Property grounds
Exceptional
(66 reviews)

OCEANFRONT VILLA AMAZING VIEW. # 363

Hilton Head Island

7% off
S$1,570
for 7 nights, 1 villa
S$224 per night
includes taxes & fees
OCEANFRONT VILLA AMAZING VIEW. # 363
Room
Pool
Dining
Living area
Exceptional
(78 reviews)

Sunrise on the ocean - Best beach & pool view-Villamare

Hilton Head Island

15% off
S$4,736
for 7 nights, 1 apartment
S$677 per night
includes taxes & fees
Sunrise on the ocean - Best beach & pool view-Villamare
Living area
Pool
Private kitchen
Interior
Exceptional
(124 reviews)

Beach Front with Ocean View

Hilton Head Island

7% off
S$1,315
for 7 nights, 1 apartment
S$188 per night
includes taxes & fees
Beach Front with Ocean View
Pool
Living area
Dining
Private kitchen
Exceptional
(106 reviews)

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

Hilton Head Island

7% off
S$2,265
for 7 nights, 1 apartment
S$324 per night
includes taxes & fees
Fabulously Updated 2-Bedroom, 2-Bathroom Condo With Beach Access
Great kitchen area with dishwasher!
What in incredible view!
Wonderful living and dining and kitchen area! Ceiling fan and great views!
Wonderful pool area to play or relax!
Exceptional
(98 reviews)

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

Hilton Head Island

7% off
S$1,644
for 7 nights, 1 home
S$235 per night
includes taxes & fees
Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380
Hilton Head Island - Shelter Cove Harbour & Marina
The fully-equipped kitchen, upgraded with granite countertops and stainless steel appliances, invites culinary adventures with local specialties.
Brand new granite countertops
Savor your morning coffee or enjoy happy hour with loved ones on the covered patio, where a fresh marine breeze adds to the ambiance.
Wonderful
(7 reviews)

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

Hilton Head Island

5% off
S$2,141
for 7 nights, 1 apartment
S$306 per night
includes taxes & fees
7104 Harbourside 1 @ Shelter Cove | Pool | Stunning Marina Views
Private kitchen
Interior
Living area
Living area
Exceptional
(15 reviews)

"Nanas Haven" Family Friendly 2B2B, 1st floor end unit

Hilton Head Island

7% off
S$1,780
for 7 nights, 1 apartment
S$254 per night
includes taxes & fees
"Nanas Haven" Family Friendly 2B2B, 1st floor end unit
Property grounds
Harbourtown Lighthouse
Anti-gravity chairs on balcony
Living room/kitchen.
Exceptional
(197 reviews)

AWESOME REMODEL! FREE BIKES, ALL BEACH GEAR, on the beach, 5-star reviews.

Hilton Head Island

7% off
S$2,064
for 7 nights, 1 apartment
S$295 per night
includes taxes & fees
AWESOME REMODEL! FREE BIKES, ALL BEACH GEAR, on the beach, 5-star reviews.
Living Room area with fold out sofa, recliner. Plenty of seating
Seats four at island dining. Spacious handicap friendly 1st floor.
Back Patio and screened in poarch leading to pool
Property grounds
Exceptional
(89 reviews)

604 Tennismaster, OWNER Mgmt, Beach Locker, Handicap & Family Friendly

Hilton Head Island

10% off
S$2,748
for 7 nights, 1 home
S$393 per night
includes taxes & fees
604 Tennismaster, OWNER Mgmt, Beach Locker, Handicap & Family Friendly
Fully stocked kitchen area.
Ocean View!
Air Conditioner in bedroom.
Seaside Villas!
Exceptional
(81 reviews)

One of a Kind! High End Condo! 1 bed, 1 ba, Ocean View, 2 Bikes! #109

Hilton Head Island

7% off
S$1,453
for 7 nights, 1 apartment
S$208 per night
includes taxes & fees
One of a Kind! High End Condo! 1 bed, 1 ba, Ocean View, 2 Bikes! #109
Room
Visit Beautiful Shelter Cove-less than 2 miles away!
Exercise Room
Jamaica Joe’z Beach and Poolside Bar
Exceptional
(156 reviews)

Experience Luxury at the Beach! Oceanside Resort! Huge Oceanside Pool!

Hilton Head Island

7% off
S$2,590
for 7 nights, 1 villa
S$370 per night
includes taxes & fees
Experience Luxury at the Beach! Oceanside Resort! Huge Oceanside Pool!
To your left from the entrance, a fully-equipped kitchen awaits. The open-concept living and dining area ensures that everyone in the group stays included in the conversation and admires the culinary adventures of the chef among you.
Hilton Head Island - Shelter Cove Harbour & Marina
Hilton Head Island's renowned Golf Courses
Pickleball and Tennis at Sea Pines
Exceptional
(9 reviews)

148 Island House @ Forest Beach | Walk to Beach | Pool | Pet-Friendly | Tennis

Hilton Head Island

5% off
S$1,957
for 7 nights, 1 villa
S$280 per night
includes taxes & fees
148 Island House @ Forest Beach | Walk to Beach | Pool | Pet-Friendly | Tennis
Queen bed, lots of storage! Bedroom is open to hallway.
Sea Sides private sun deck!
Boardwalk from beach to Sea Side Villas, only a minute walk, showers at end!
Beautiful artwork through the entire condo!
Exceptional
(281 reviews)

OCEAN VIEW! Coligny Area! UPDATED~1 BD, 1 BA ~2 Bikes! #113

Hilton Head Island

7% off
S$1,493
for 7 nights, 1 apartment
S$213 per night
includes taxes & fees
OCEAN VIEW! Coligny Area! UPDATED~1 BD, 1 BA ~2 Bikes! #113
Interior
Property grounds
Interior
Pool
Wonderful
(7 reviews)

Beachfront Villa 2BR with indoor and outdoor Pool, Hot Tub, Sauna & Fitness Room

Hilton Head Island

7% off
S$1,736
for 7 nights, 1 apartment
S$248 per night
includes taxes & fees
Beachfront Villa 2BR with indoor and outdoor Pool, Hot Tub, Sauna & Fitness Room
Marina
Marina
Marina
Living area
Exceptional
(20 reviews)

Spacious Condo in the heart of Harbor Town!

Hilton Head Island

16% off
S$1,930
for 7 nights, 1 apartment
S$276 per night
includes taxes & fees
Spacious Condo in the heart of Harbor Town!
Queen size bed, flat screen TV, DVD player, private room!
Wonderful view of the ocean, so relaxing!
Wonderful airy and bright open concept!
Lots of storage in the kitchen!
Exceptional
(102 reviews)

Awesome Ocean View! Coligny Area! UPDATED and CLEAN 1 Bedroom! 2 Bikes! #132

Hilton Head Island

7% off
S$1,493
for 7 nights, 1 apartment
S$213 per night
includes taxes & fees
Awesome Ocean View! Coligny Area! UPDATED and CLEAN 1 Bedroom! 2 Bikes! #132
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    Enjoy full kitchens, laundry, pools, gardens and more
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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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