Hilton Head Island holiday rentals

We found 10,234 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
Pool
Exceptional
(184 reviews)

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

Hilton Head Island

7% off
S$5,629
for 7 nights, 1 home
S$804 per night
includes taxes & fees
5th Row, Sea Pines-South Beach, Private Pool, Private Path to Beach, 4 EnSuites
Living area
Dining
Exterior
Private kitchen
Wonderful
(88 reviews)

South Beach Dog-friendly Waterfront Villa

Hilton Head Island

8% off
S$3,618
for 7 nights, 1 villa
S$517 per night
includes taxes & fees
South Beach Dog-friendly Waterfront Villa
Basking in the warmth of a sun-kissed day, our private pool is a haven of joy.
Dining
Private kitchen
Interior
Exceptional
(63 reviews)

Cozy Ranch with Private Heated Pool, Hot Tub, King Bed, Prime Location, Clean

Hilton Head Island

7% off
S$7,758
for 7 nights, 1 home
S$1,108 per night
includes taxes & fees
Cozy Ranch with Private Heated Pool, Hot Tub, King Bed, Prime Location, Clean
Comfortable Living Room
Palmetto Dunes Tennis and Pickleball Center - 10 minute walk
Dunes House on the Beach - 15 minute walk
22 Hickory Cove
Exceptional
(106 reviews)

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

Hilton Head Island

7% off
S$2,806
for 7 nights, 1 villa
S$401 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
Second level has a loft kitchenette area with access to the balcony
Hilton Head Island - Shelter Cove Harbour & Marina
Exceptional
(6 reviews)

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

Hilton Head Island

5% off
S$11,139
for 7 nights, 1 home
S$1,591 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
A nice large smart TV with games and books in the cabinet
Exceptional
(22 reviews)

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

Hilton Head Island

7% off
S$3,240
for 7 nights, 1 villa
S$463 per night
includes taxes & fees
Beautiful Lagoon/Golf Views! Short Walk/Bike Ride to Beach Club
Elevator nearby
Enjoy sunrise right at balcony
Living room and kitchen
Open bedroom
Excellent
(171 reviews)

Admirals Row 306: True Direct Oceanfront W/Panoramic Oceanview

Hilton Head Island

8% off
S$2,353
for 7 nights, 1 villa
S$336 per night
includes taxes & fees
Admirals Row 306: True Direct Oceanfront W/Panoramic Oceanview
Building 3/Atrium - wi-fi lounge.
Coco's on the Beach at end of boardwalk.
Living area
Living area
Exceptional
(94 reviews)

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

Hilton Head Island

8% off
S$3,657
for 7 nights, 1 villa
S$522 per night
includes taxes & fees
7-Day Discounts in 3BR Villa at Hilton Head Resort!
Turnberry pool is directly behind villa - just steps away!
Living area
Terrace/patio
Ground level entry
Exceptional
(84 reviews)

3BR Palmetto Dunes villa in beautiful, tranquil neighborhood-walk/bike to beach!

Hilton Head Island

7% off
S$2,872
for 7 nights, 1 villa
S$410 per night
includes taxes & fees
3BR Palmetto Dunes villa in beautiful, tranquil neighborhood-walk/bike to beach!
Jamaica Joe's beach bar right in boardwalk and next to pool
Fireworks at Shelter Cove
The pirates ship at Celebration Park
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$1,946
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🌴🌺☀️
Living area
Looking from Entry through the Villa
Dining
King Comfort
Exceptional
(61 reviews)

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

Hilton Head Island

7% off
S$2,150
for 7 nights, 1 villa
S$307 per night
includes taxes & fees
Oceanside Resort! King Master Suite, Sleeps 6, Walk to the Beach!
A glass of wine anyone?
What a beautiful way to celebrate a special day!
Private kitchen
Private kitchen
Exceptional
(136 reviews)

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

Hilton Head Island

7% off
S$2,236
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!
Living area
Lagoon view
Pool
View of back
Exceptional
(119 reviews)

Lovely Villa near Harbour Town For couple

Hilton Head Island

8% off
S$1,612
for 7 nights, 1 villa
S$230 per night
includes taxes & fees
Lovely Villa near Harbour Town For couple
Exterior detail
Children’s area
Dining
Property grounds
Exceptional
(66 reviews)

OCEANFRONT VILLA AMAZING VIEW. # 363

Hilton Head Island

7% off
S$1,560
for 7 nights, 1 villa
S$223 per night
includes taxes & fees
OCEANFRONT VILLA AMAZING VIEW. # 363
Enjoy the water
Plenty of relaxing outdoor space
Ample dining space
High ceilings abound
Exceptional
(12 reviews)

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

Hilton Head Island

15% off
S$3,211
for 7 nights, 1 home
S$459 per night
includes taxes & fees
Family-oriented lagoon-side home in Sea Pines close to Harbour Town
Living area
Living area
Living area
Room
Exceptional
(13 reviews)

The Admiral's Roost ~ Steps to the beach and pool. Perfect for couples

Hilton Head Island

7% off
S$1,879
for 7 nights, 1 apartment
S$268 per night
includes taxes & fees
The Admiral's Roost ~ Steps to the beach and pool. Perfect for couples
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!
Front view of condo - ground level
Living area with new sleeper sofa
Exceptional
(139 reviews)

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

Hilton Head Island

8% off
S$1,704
for 7 nights, 1 villa
S$243 per night
includes taxes & fees
Book now for Fall 2026! Short walk to park/playground & Beach, near Coligny
Kitchen at 2388 Lighthouse Tennis Villas
Free access to the Sea Pines Beach Club a short bike ride away!
Living Room at 2388 Lighthouse Tennis Villas
Lagoon Views from 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$2,561
for 7 nights, 1 apartment
S$366 per night
includes taxes & fees
Center of Sea Pines; View of Lagoon; Walkable to Harbour Town/Beach Club/Market
Robert Trent Jones golf course - Palmetto Dunes - adjacent to Hilton Head Resort
One of three Hilton Head Resort pools located right below our villa
Living Area
Full kitchen with granite counters & tiled backsplash
Exceptional
(105 reviews)

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

Hilton Head Island

7% off
S$1,618
for 7 nights, 1 apartment
S$231 per night
includes taxes & fees
Stunning Ocean & Tidal Creek Views -- Best Resort Vantage Point!
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.
Brand new granite countertops
Hilton Head Island - Shelter Cove Harbour & Marina
Excellent
(8 reviews)

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

Hilton Head Island

5% off
S$2,123
for 7 nights, 1 apartment
S$303 per night
includes taxes & fees
7104 Harbourside 1 @ Shelter Cove | Pool | Stunning Marina Views
Indoor-Outdoor concept with large sliding doors and vaulted ceilings
Hilton Head Island - Shelter Cove Harbour & Marina
Smart TV  for movie nights or watching a game
Pickleball and Tennis at Sea Pines
Exceptional
(13 reviews)

2319 Racquet Club @ Sea Pines | Steps to Beach | Pool & Lagoon Views | Golf | Tennis

Hilton Head Island

5% off
S$2,025
for 7 nights, 1 apartment
S$289 per night
includes taxes & fees
2319 Racquet Club @ Sea Pines | Steps to Beach | Pool & Lagoon Views | Golf | Tennis
Comfortable island living
The Sea Pines Beach Club
New Plantation Club golf complex
Harbour Town marina
Exceptional
(17 reviews)

SeaPines Cheerful Pet Friendly Home by the Beach

Hilton Head Island

7% off
S$3,531
for 7 nights, 1 home
S$504 per night
includes taxes & fees
SeaPines Cheerful Pet Friendly Home by the Beach
Dining
Property grounds
Private kitchen
Living area
Exceptional
(31 reviews)

Relaxing 2BR/2Ba Condo in HHI, minutes from the beach

Hilton Head Island

7% off
S$1,124
for 7 nights, 1 apartment
S$161 per night
includes taxes & fees
Relaxing 2BR/2Ba Condo in HHI, minutes from the beach
Interior
Interior
Private kitchen
Living area
Exceptional
(15 reviews)

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

Hilton Head Island

7% off
S$1,762
for 7 nights, 1 apartment
S$252 per night
includes taxes & fees
"Nanas Haven" Family Friendly 2B2B, 1st floor end unit
  • 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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