Hilton Head Island holiday rentals

We found 10,314 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

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

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

Hilton Head Island

7% off
S$5,627
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
Dunes House on the Beach - 15 minute walk
Palmetto Dunes Tennis and Pickleball Center - 10 minute walk
Comfortable Living Room
Fully Equipped Kitchen
Exceptional
(106 reviews)

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

Hilton Head Island

7% off
S$2,805
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!!
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
Atlantic Dunes by Davis Love III
Kitchen
Exceptional
(22 reviews)

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

Hilton Head Island

7% off
S$3,238
for 7 nights, 1 villa
S$463 per night
includes taxes & fees
Beautiful Lagoon/Golf Views! Short Walk/Bike Ride to Beach Club
Second level has a loft kitchenette area with access to the balcony
Elegant windows with views of the outdoors
Hilton Head Island - Shelter Cove Harbour & Marina
Dining table with seating for 8
Exceptional
(6 reviews)

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

Hilton Head Island

5% off
S$11,148
for 7 nights, 1 home
S$1,593 per night
includes taxes & fees
20 Knotts Way @ North Forest Beach | Luxury Retreat | Steps from the Beach | Loaded with Amenities
Living area
Pool
Beach
Aerial View - only steps away from the ocean
Exceptional
(8 reviews)

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

Hilton Head Island

14% off
S$8,236
for 7 nights, 1 home
S$1,177 per night
includes taxes & fees
55 Steps To The Beach - 2nd Row Ocean - Private Pool
Elevator nearby
Enjoy sunrise right at balcony
Open bedroom
Admirals Row Building is right on the beach
Excellent
(171 reviews)

Admirals Row 306: True Direct Oceanfront W/Panoramic Oceanview

Hilton Head Island

8% off
S$2,352
for 7 nights, 1 villa
S$336 per night
includes taxes & fees
Admirals Row 306: True Direct Oceanfront W/Panoramic Oceanview
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$2,856
for 7 nights, 1 villa
S$408 per night
includes taxes & fees
3BR Palmetto Dunes villa in beautiful, tranquil neighborhood-walk/bike to beach!
Entrance sign to resort at Highway 278.
Coco's on the Beach at end of boardwalk.
Building 3/Atrium - wi-fi lounge.
Living area
Exceptional
(94 reviews)

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

Hilton Head Island

8% off
S$3,656
for 7 nights, 1 villa
S$522 per night
includes taxes & fees
7-Day Discounts in 3BR Villa at Hilton Head Resort!
Marina
Marina
Outdoor dining
Pool
Exceptional
(42 reviews)

Great for Families! Lg Pool, Near Harbour Town, Beach, Golf, Tennis & Pickleball

Hilton Head Island

7% off
S$3,641
for 7 nights, 1 villa
S$520 per night
includes taxes & fees
Great for Families! Lg Pool, Near Harbour Town, Beach, Golf, Tennis & Pickleball
The pirates ship at Celebration Park
Fireworks at Shelter Cove
Lots of dining and shopping at Shelter Cove
Jamaica Joe's beach bar right in boardwalk and next to pool
Exceptional
(74 reviews)

GREAT OCEAN VIEW to Relax, Rest, and Restore on Beautiful Hilton Head Island🌴🌺☀️

Hilton Head Island

7% off
S$1,945
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🌴🌺☀️
King Comfort
Looking from Entry through the Villa
Living area
Kiddie Pool on a quiet Evening
Exceptional
(61 reviews)

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

Hilton Head Island

7% off
S$2,149
for 7 nights, 1 villa
S$307 per night
includes taxes & fees
Oceanside Resort! King Master Suite, Sleeps 6, Walk to the Beach!
Living area
The beach in front of Hilton Head Resort is beautiful with much less traffic.
Sleeper sofa in main room - with flat screen TV. Breakfast bar with granite top.
Private kitchen
Exceptional
(104 reviews)

FIRE SALE 25% OFF August Hltn Head Resrt 2BR/2BA: GLF/MRSH/OCEN VIEW. BEST BEACH

Hilton Head Island

8% off
S$1,735
for 7 nights, 1 apartment
S$248 per night
includes taxes & fees
FIRE SALE 25% OFF August Hltn Head Resrt 2BR/2BA: GLF/MRSH/OCEN VIEW. BEST BEACH
Private kitchen
What a beautiful way to celebrate a special day!
A glass of wine anyone?
Private kitchen
Exceptional
(136 reviews)

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

Hilton Head Island

7% off
S$2,235
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$1,611
for 7 nights, 1 villa
S$230 per night
includes taxes & fees
Lovely Villa near Harbour Town For couple
Private kitchen
Children’s area
Exterior detail
Property grounds
Exceptional
(66 reviews)

OCEANFRONT VILLA AMAZING VIEW. # 363

Hilton Head Island

7% off
S$1,559
for 7 nights, 1 villa
S$223 per night
includes taxes & fees
OCEANFRONT VILLA AMAZING VIEW. # 363
Ample dining space
Plenty of relaxing outdoor space
Cook
Enjoy the water
Exceptional
(12 reviews)

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

Hilton Head Island

15% off
S$3,209
for 7 nights, 1 home
S$458 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$1,629
for 7 nights, 1 apartment
S$233 per night
includes taxes & fees
The Admiral's Roost ~ Steps to the beach and pool. Perfect for couples
Living area with new sleeper sofa
Brand new kids' playground at Low Country Celebration Park - go explore!
Front view of condo - ground level
Entry area with storage for shoes, jackets, beach towels, bike helmets, etc.
Exceptional
(139 reviews)

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

Hilton Head Island

8% off
S$1,703
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
Harbour Town!
Free access to the Sea Pines Beach Club a short bike ride away!
Lagoon Views from 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$2,560
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
Dining area looking out to balcony
One of three Hilton Head Resort pools located right below our villa
Robert Trent Jones golf course - Palmetto Dunes - adjacent to Hilton Head Resort
Full kitchen with granite counters & tiled backsplash
Exceptional
(106 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.
After a day of exploring the island, unwind in a comfortable bed with the finest quality bedding, ensuring a restful night's sleep.
Brand new granite countertops
Excellent
(8 reviews)

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

Hilton Head Island

5% off
S$2,124
for 7 nights, 1 apartment
S$303 per night
includes taxes & fees
7104 Harbourside 1 @ Shelter Cove | Pool | Stunning Marina Views
Hilton Head Island's renowned Golf Courses
Hilton Head Island - Shelter Cove Harbour & Marina
Pickleball and Tennis at Sea Pines
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.
Exceptional
(9 reviews)

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

Hilton Head Island

5% off
S$1,955
for 7 nights, 1 villa
S$279 per night
includes taxes & fees
148 Island House @ Forest Beach | Walk to Beach | Pool | Pet-Friendly | Tennis
Living area
Property grounds
Private kitchen
Dining
Exceptional
(31 reviews)

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

Hilton Head Island

6% off
S$1,109
for 7 nights, 1 apartment
S$158 per night
includes taxes & fees
Relaxing 2BR/2Ba Condo in HHI, minutes from the beach
Beautiful artwork through the entire condo!
Sea Sides private sun deck!
Queen bed, lots of storage! Bedroom is open to hallway.
Boardwalk from beach to Sea Side Villas, only a minute walk, showers at end!
Exceptional
(281 reviews)

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

Hilton Head Island

7% off
S$1,483
for 7 nights, 1 apartment
S$212 per night
includes taxes & fees
OCEAN VIEW! Coligny Area! UPDATED~1 BD, 1 BA ~2 Bikes! #113

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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