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Hilton Head Island vacation rentals

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Best Hilton Head Island vacation rentals

These are the best prices for Oct 17 - 18.
Hilton Head Island Condo w/ Coligny Beach Access! - Hilton Head Island - Living room
Hilton Head Island Condo w/ Coligny Beach Access!
Hilton Head Island, SC
9.7Wonderful(34)
Condo
$195+
Check availability
Marriott's Surf Watch, A Marriott Vacation Club Resort - Hilton Head Island - Pool
Marriott's Surf Watch, A Marriott Vacation Club Resort
Hilton Head Island, SC
9.4Wonderful(57)
Condo
$605+
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Village House 102 - Hilton Head Island
Village House 102
Hilton Head Island, SC
8.9Very good(20)
Apartment
$196+
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Spacious, cozy villa w/parking in Coligny Villas - Hilton Head Island - Bedroom
Spacious, cozy villa w/parking in Coligny Villas
Hilton Head Island, SC
8.9Very good(40)
Villa
$325+
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'Couples & Family Getaway,' 1st Floor, King & Queen Beds, Pool, 42' Hdtv's, Wifi - Hilton Head Island - Living room
'Couples & Family Getaway,' 1st Floor, King & Queen Beds, Pool, 42' Hdtv's, Wifi
Hilton Head Island, SC
9.5Wonderful(34)
Villa
$198+
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Village House 303, 2 Bedrooms, Sleeps 6, - Hilton Head Island - Living room
Village House 303, 2 Bedrooms, Sleeps 6,
Hilton Head Island, SC
9.0Wonderful(20)
Condo
$217+
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Beachfront Condo w/ Pool Access in Hilton Head! - Hilton Head Island - Living room
Beachfront Condo w/ Pool Access in Hilton Head!
Hilton Head Island, SC
9.4Wonderful(43)
Condo
$286+
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Walk to Pier & Golf: Heart of Harbour Town Condo - Hilton Head Island - Building
Walk to Pier & Golf: Heart of Harbour Town Condo
Harbour Town
9.9Wonderful(54)
Condo
$348+
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Direct Oceanfront Villa - Heated Pool & Breathtaking Ocean View - Hilton Head Island - Pool
Direct Oceanfront Villa - Heated Pool & Breathtaking Ocean View
Hilton Head Island, SC
9.4Wonderful(68)
Villa
$312+
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4102 Windsor Court-Oceanviews And Coastal Inspired - Hilton Head Island - Pool
4102 Windsor Court-Oceanviews And Coastal Inspired
Hilton Head Island, SC
9.0Wonderful(26)
Condo
$325+
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Walk to Forest Beach: Hilton Head Getaway! - Hilton Head Island - Pool
Walk to Forest Beach: Hilton Head Getaway!
Hilton Head Island, SC
9.5Wonderful(17)
Apartment
$244+
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Beautiful 3 BR Villa Across From Beach w/Lagoon & Golf View & 2 Private Decks - Hilton Head Island - Dining room
Beautiful 3 BR Villa Across From Beach w/Lagoon & Golf View & 2 Private Decks
Hilton Head Island, SC
9.9Wonderful(32)
Villa
$317+
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Hilton Head Island Escape - Walk to Beach! - Hilton Head Island - Balcony
Hilton Head Island Escape - Walk to Beach!
Hilton Head Island, SC
8.6Very good(35)
Villa
$264+
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333 Breakers - 3rd Floor Ocean View Villa - Hilton Head Island - Living room
333 Breakers - 3rd Floor Ocean View Villa
Hilton Head Island, SC
9.1Wonderful(28)
Condo
$269+
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Springwood Villas with pool excess half a mile from beach - Hilton Head Island
Springwood Villas with pool excess half a mile from beach
Hilton Head Island, SC
8.5Very good(15)
Apartment
$242+
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Near Beach & Coligny Plaza, Pool, Hot Tub, Patio - Hilton Head Island
Near Beach & Coligny Plaza, Pool, Hot Tub, Patio
Hilton Head Island, SC
9.1Wonderful(12)
Apartment
$364+
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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 December, with average rates of $155. In comparison, July is the most expensive month, with prices at $879.

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

Wednesday offers the lowest rates in Hilton Head Island, with an average nightly price of $260. The highest prices are found on Saturday, with average rates at $436.

How much is a vacation rental in Hilton Head Island for tonight by property type?

The best deal for a vacation rental in Hilton Head Island found by KAYAK users in the last 5 days was $256 in a House. Apartment prices start at $269.

How much is a vacation rental in Hilton Head Island for this weekend by property type?

The best deal for a vacation rental in Hilton Head Island found by KAYAK users for the upcoming weekend was $205 in a Condo. Apartments prices start at $215, Villas at $329, Houses at $353, and Cottages at $354.

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

Book at least 30 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
$353
$394
Cheapest month to stay with an average 46% drop in price.
Most expensive month to stay with an average 128% 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.
  • Kitchen/Kitchenette, beachfront, air-conditioned, pet friendly, pool, and wifi are the most popular vacation rental property amenities in Hilton Head Island
  • Vacation rentals in Hilton Head Island are around 80% cheaper 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 Walk to Pier & Golf: Heart of Harbour Town Condo (9.9, 54 reviews), Beautiful 3 BR Villa Across From Beach w/Lagoon & Golf View & 2 Private Decks (9.9, 32), and Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown (9.8, 110), 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 Wednesday. In contrast, the most expensive is Saturday.
  • 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 4 days.

FAQs when booking a vacation home in Hilton Head Island

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

    The average price for a weekly Hilton Head Island vacation rental found by KAYAK users in the last 2 weeks is $2,535.

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

    The average price for a monthly Hilton Head Island vacation rental found by KAYAK users in the last 2 weeks is $10,865.

  • What types of vacation rentals are available in Hilton Head Island?

    There are loads of different property types that you can make your vacation home in Hilton Head Island. You’ll find apartments, aparthotels, condos, cottages, houses, holiday parks, homestays, hotels, resorts, timeshares and villas.

  • What are some of the most-loved vacation rentals available in Hilton Head Island?

    There are many types of properties available for Hilton Head Island vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Marriott's Surf Watch, A Marriott Vacation Club Resort and Steps to Beach! Top-Floor Condo in Hilton Head.

  • What are the most popular Hilton Head Island vacation rentals for a large group?

    If you’re a large group then you’ll need plenty of space. The highest rated vacation homes that can sleep 6 people or more by KAYAK users are Walk to Beach: Hilton Head Resort Condo w/ Pools!, Walk to Beach: Family Hilton Head Island Condo and Ocean Views and 3 Pools Hilton Head Resort Condo.

  • Are there any pet-friendly vacation rentals in Hilton Head Island?

    There are a number of dog and pet-friendly Hilton Head Island vacation rentals, with around 7% allowing you to bring your pet along with you.

  • How much is a vacation rental in Hilton Head Island for tonight?

    In the last 72 hours, users have found Hilton Head Island vacation rentals for tonight for as low as $256. Search here for similar prices

  • How much is a vacation rental in Hilton Head Island for this weekend?

    In the last 72 hours, users have found Hilton Head Island vacation rentals for this weekend for as low as $205 per night. Search here for similar prices

  • How can I find vacation rentals near me in Hilton Head Island?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

  • 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.

More options for your stay in Hilton Head Island