Hilton Head Island vacation rentals

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Best Hilton Head Island vacation rentals

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$53 - $585$585 - $1,117$1,117 - $1,649$1,649 - $2,181$2,181+ per night

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Most recommended vacation rentals in Hilton Head Island

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Hilton Head Island Beach & Tennis Resort - Hilton Head Island - Pool
Hilton Head Island Beach & Tennis Resort
Hilton Head Island, SC
8.6Very good(7)
Parking
Free Wi-Fi
Pool
$126+
Check availability
Beach Access Oceanfront Hilton Head Studio - Hilton Head Island - Living room
Beach Access Oceanfront Hilton Head Studio
Hilton Head Island, SC
8.5Very good(40)
Free Wi-Fi
$180+
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Walk to Beach: Hilton Head Island Tennis Retreat! - Hilton Head Island - Pool
Walk to Beach: Hilton Head Island Tennis Retreat!
Hilton Head Island, SC
8.6Very good(20)
Free Wi-Fi
$137+
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Hilton Head Resort Condo w/ Resort Amenities - Hilton Head Island - Pool
Hilton Head Resort Condo w/ Resort Amenities
Hilton Head Island, SC
9.2Wonderful(32)
$181+
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Oceanfront Hilton Head Island Condo with Pool! - Hilton Head Island - Living room
Oceanfront Hilton Head Island Condo with Pool!
Hilton Head Island, SC
8.3Very good(42)
Free Wi-Fi
Pool
$168+
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Steps to Pool and Beach Family Condo in Hilton Head - Hilton Head Island - Bedroom
Steps to Pool and Beach Family Condo in Hilton Head
Hilton Head Island, SC
9.5Wonderful(28)
Free Wi-Fi
Pool
$214+
Check availability
Top-floor Condo w/ Ocean Views in Hilton Head! - Hilton Head Island - Pool
Top-floor Condo w/ Ocean Views in Hilton Head!
Hilton Head Island, SC
10Wonderful(2)
Free Wi-Fi
$178+
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Folly Field Beach Access Resort Condo with Pools - Hilton Head Island - Pool
Folly Field Beach Access Resort Condo with Pools
Hilton Head Island, SC
9.3Wonderful(36)
Free Wi-Fi
Pool
$145+
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Pool & Beach Access: Hilton Head Coastal Condo - Hilton Head Island - Living room
Pool & Beach Access: Hilton Head Coastal Condo
Hilton Head Island, SC
9.8Wonderful(20)
Free Wi-Fi
$213+
Check availability
Direct Oceanfront Villa - Heated Pool & Breathtaking Ocean View - Hilton Head Island - Pool
Direct Oceanfront Villa - Heated Pool & Breathtaking Ocean View
Hilton Head Island, SC
9.2Wonderful(55)
Parking
Free Wi-Fi
Pool
$235+
Check availability
Beach View, Pool and Tennis Hilton Head Island Unit - Hilton Head Island - Pool
Beach View, Pool and Tennis Hilton Head Island Unit
Hilton Head Island, SC
8.8Very good(40)
Free Wi-Fi
$203+
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Ocean View at Island Club - Hilton Head Island - Balcony
Ocean View at Island Club
Hilton Head Island, SC
9.6Wonderful(35)
Parking
Free Wi-Fi
Pool
$175+
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Pool Access Idyllic Sea Pines Gem, Walk to Beach - Hilton Head Island - Building
Pool Access Idyllic Sea Pines Gem, Walk to Beach
Hilton Head Island, SC
8.8Very good(22)
Free Wi-Fi
$220+
Check availability
Walk to Bars and Shops Resort Condo in Hilton Head! - Hilton Head Island - Pool
Walk to Bars and Shops Resort Condo in Hilton Head!
Hilton Head Island, SC
8.1Very good(24)
Free Wi-Fi
Pool
$194+
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Private Beach Access: Hilton Head Island Condo! - Hilton Head Island - Pool
Private Beach Access: Hilton Head Island Condo!
Hilton Head Island, SC
9.6Wonderful(29)
Free Wi-Fi
$170+
Check availability
Salty Shores! -Incredible ocean views - Hilton Head Island - Living room
Salty Shores! -Incredible ocean views
Hilton Head Island, SC
9.0Wonderful(19)
Parking
Free Wi-Fi
Pool
$219+
Check availability
Booking Insights

KAYAK’s insights for vacation rentals in Hilton Head Island

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Hilton Head Island with confidence.

Which month has the cheapest vacation rental rates in Hilton Head Island?

Vacation rentals are cheapest in Hilton Head Island in January, with average rates of $156. In comparison, July is the most expensive month, with prices at $985.

What is the cheapest day of the week to book a vacation rental in Hilton Head Island?

Monday offers the lowest rates in Hilton Head Island, with an average nightly price of $283. The highest prices are found on Friday, with average rates at $469.

How early should you book a vacation rental in Hilton Head Island?

Book at least 26 days before your stay begins to get the best price for your Hilton Head Island vacation rental.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
July
$381
$412
Cheapest month to stay with an average 68% drop in price.
Most expensive month to stay with an average 102% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Hilton Head Island vacation rental deals

  • If you’re traveling with your furry friend to Hilton Head Island, you’ll find what you’re looking for through KAYAK’s pet-friendly vacation rentals. Stay somewhere like the Pet-Friendly Resort Villa with Fenced Yard and BBQ. The yard is great for a pet to hang out as well as being near pet-friendly beaches and just about two miles from the Chaplin Best Friends Dog Park.
  • For those in town who wish to be near the airport, you can stay at Hilton Head Island house rentals like the Large & Affordable Town Home #37. This place sleeps six and is just a mile and a half from the Hilton Head Airport.
  • If you’re visiting Hilton Head Island and require facilities with increased accessibility, The Pet-Friendly Resort Villa that has fenced yard and BBQ is an entire unit located on the ground floor as well as accessible for limited mobility.
  • Hilton Head Island is a great destination for outdoor activities. If you’re visiting the area and enjoy biking and hiking, you can stay at Hilton Head Island vacation rentals like the Sea Pines Resort Home with Deck – Drive to the Beach. The Audubon Newhall Preserve is less than half a mile away.
  • If you’re looking to enjoy the Hilton Head Island nightlife during your stay, we suggest looking for a vacation rental near Pope Avenue. The Condo with Discounted Rates Walk to Beach and Pool would be a good option.
  • Beachfront, hot tub, pet friendly, kitchen/kitchenette, and pool are the most popular vacation rental property amenities in Hilton Head Island
  • Vacation rentals in Hilton Head Island are around 77% more expensive than hotels on average. Search here to compare prices for all accommodation types in Hilton Head Island.
  • The best vacation rental properties in Hilton Head Island are Pool & Beach Access: Hilton Head Coastal Condo (9.8, 20 reviews), Private Beach Access: Hilton Head Island Condo! (9.6, 29), and Ocean View at Island Club (9.6, 35), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Hilton Head Island, you should consider visiting during the low season. The cheapest vacation homes in Hilton Head Island can be found in January and February.
  • The cheapest night for renting a vacation home in Hilton Head Island is Saturday. In contrast, the most expensive is Wednesday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Hilton Head Island for 3 days.

FAQs when booking a vacation home in Hilton Head Island

  • How much is a Rental rental for a week in Hilton Head Island?

    The average price for a weekly Hilton Head Island Rental rental found by KAYAK users in the last 2 weeks is $1,393. Though this can obviously vary depending on the time of year of your stay and when you make the booking.

  • How much is a Rental rental for a month in Hilton Head Island?

    The average price for a monthly Hilton Head Island Rental rental found by KAYAK users in the last 2 weeks is $12,302.

  • Where is a good place to stay on Hilton Head Island with children?

    For those visiting with their family and children, there are great Hilton Head Island vacation rentals for you. Take the Mid-Island Marvel W/ Resort Amenities 2 Bedroom Condo for example, the resort has a pool and is near Coligny Beach. Shelter Cove Harbor is just about a 6-minute drive away where you’ll find shops, restaurants, and a playground.

  • Which vacation rentals have a beachfront view in Hilton Head Island?

    Hilton Head Island is known for its beautiful dunes and beaches. Find a vacation rental along the coast like the Direct Ocean Front First Floor 1br/1bath Condo. From your window, you can see the ocean and you won’t have to cross any streets to get there. The beach is just 1-min away.

  • Where is a good place to stay to enjoy Hilton Head Island golfing?

    There are various golf courses in the Hilton Head Island area, so most likely any of the vacation rental options will be near a course. The Newly Remodeled Near Harbour Town, 2 bedroom villa, is near both the Harbor Town Golf Links 18-hole course as well as Heron Point by Pete Dye.

  • Where to stay on a business trip to Hilton Head Island?

    If you’re in town on a business trip or need to get work done during your stay, look for a secluded spot away from top destinations like Harbour Town or Coligny. Hilton Head Island vacation rentals like Colonnade Club 152 could be a good choice. This rental offers free internet access and air-conditioned units.

Where to stay in Hilton Head Island?

Our map will help you find the perfect place to stay in Hilton Head Island by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Hilton Head Island

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