Hilton Head Island Vacation Rentals

Our Favorite Vacation Rentals in Hilton Head Island

  • New Listing! Resort Condo W/ Pools & Beach Shuttle Villa
     Villa
    Booking.com
    From
    $117
  • Spectacular Villa, Breathtaking Views of Harbor!
    Good3br Country House
    HolidayLettings
    From
    $384
  • Home Away Home #2
    GoodCountry House
    Booking.com
    From
    $138
  • Book Your Summer Stay! Oceanfront Villa!
    ExcellentCountry House
    HolidayLettings
    From
    $186
  • Home Away Home #50
     Country House
    Booking.com
    From
    $99
  • BEAUTIFUL VILLA!! POOL AT YOUR DOOR! BEACH STEPS AWAY ! 100.00 RESERVES ME!!!
    Excellent2br Country House
    HolidayLettings
    From
    $180
  • Island Club Condos
    GoodHome/Apartment
    Booking.com
    From
    $116
  • Spacious 5 bedroom home with gorgeous lagoon views!
     5br Home/Apartment
    HolidayLettings
    From
    $428

Check prices for these upcoming dates

Hilton Head Island Vacation Rentals with a Pool

  • Island comfort room.
    ExcellentCottage
    Airbnb
    From
    $121
  • Brand New & Beautiful #58
    Good2br Home/Apartment
    Airbnb
    From
    $151
  • Island Vibe Oasis
    Excellent3br Home/Apartment
    Airbnb
    From
    $299
  • Tranquil Palm Retreat
    Excellent3br Home/Apartment
    Airbnb
    From
    $214

Hilton Head Island Vacation Rentals with Wi-Fi

  • The Private Islands of Old House Cay
    Excellent3br Home/Apartment
    Airbnb
    From
    $650
  • Shelter Cove Glamping Sailboat
    ExcellentHome/Apartment
    Airbnb
    From
    $68
  • LIVE LIKE A LOCAL: The Retreat at Broad Creek
     2br Home/Apartment
    Airbnb
    From
    $170
  • Pristine South End HHI Condo
    Excellent2br Home/Apartment
    Airbnb
    From
    $215

Hilton Head Island Pet-Friendly Vacation Rentals

  • Light-filled Home,Private pool,on Lagoon,near beach,Family & pet-friendly,Wifi
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $870
  • Bright home w/ private pool, entertainment & easy beach access - dogs ok!
     3br Home/Apartment
    HolidayLettings
    From
    $455
  • NEW! Updated Home, <1 Mile to Old Town Bluffton!
     3br Home/Apartment
    HolidayLettings
    From
    $274
  • "Banana" Caribbean-inspired, Studio Apartment
    ExcellentHome/Apartment
    HolidayLettings
    From
    $214

Hilton Head Island Travel Guide

Hilton Head Island in South Carolina is best known as a golfers paradise.

Things to Do in Hilton Head Island

When you're looking for a break from playing golf, top things to do include visiting the Harbour Town Lighthouse, exploring the Coastal Discovery Museum, which is made up of historic buildings and beautiful gardens, and spending the day at the Pinckney Island National Wildlife Refuge, where you can catch a glimpse of animals such as alligators and deer. There are also plenty of beautiful beaches nearby, where you can unwind or do a spot of watersports.

Best Time to Visit Hilton Head Island

The best time to visit Hilton Head Island is in the summer months of July and August, when the weather is hot and sunny.

A Local's Guide to Hilton Head Island Vacation Rentals

The South Carolina resort of Hilton Head Island is part of the Lowcountry region known for Atlantic Ocean beaches and golf courses. The perfect place for a family vacation, there is so much to do both on the island and the nearby mainland.

See & Do

The Harbor Town Lighthouse and Museum is on the southwest tip of the island, the Coastal Discovery Museum gives visitors a chance to discover the history of the area and there are plenty of places to take in views of the Atlantic Ocean. With 12 miles of beaches, 24 world-class golf courses, 300 tennis courts and hundreds of restaurants, bars and cafes, there are plenty of activities for travelers to enjoy.

Nature

A perfect vacation on Hilton Head Island includes lots of outdoor activities. Nature-lovers can take a trip to the Pinckney Island National Wildlife Refuge salt marsh, between the island and mainland, which is home to deer, alligators and birds.

Arts and culture enthusiasts can head to one of the many galleries in South Caroline including the Gullah museum or Heritage Library on Hilton Head.

Events

There are also many theaters on Hilton Head Island which show plays, concerts or performances throughout the year and there are also live music venues dotted around the resort.

Types of Rentals

There are hundreds of rentals in Hilton Head Island including beach houses, villas and condos, and oceanfront homes with a range of sizes and locations to suit family, friends and couples. There are places open to people on a budget that start at just $10 per night.

For working vacationers, WiFi is available at 2,612 locations and there are also 384 places with a gym on site for fitness fanatics. Pet-friendly rentals are also available for people traveling with a cat or dog and there are accommodations that also include breakfast.

Stay at a golf resort like Palmetto Dunes for on-site golfing or for an exclusive location the Port Royal Plantation is a premier private oceanfront residential community.

The peak season is in March when the rates for rooms and condos is most expensive. Vacation rentals are cheapest in September as it is the areas low season, the upside of staying in Sarasota in September is the fact the area will be quieter. Arrive midweek for the best deals and avoid weekends to get a cheaper stay.

Price and Availability in Hilton Head Island

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Hilton Head Island tends to be Saturday, while the most expensive day tends to be Monday. Vacation homes in Hilton Head Island tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Hilton Head Island is in July, while the cheapest month is in December. The most popular time to book a vacation rental in Hilton Head Island is in the high season in July. Hilton Head Island has its low season in December, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Hilton Head Island

Rainy days
88° 48°
3
81° 34°
5
72° 36°
8
75° 23°
2
79° 37°
2
84° 37°
2
82° 45°
3
90° 52°
2
97° 72°
4
93° 72°
8
93° 72°
3
93° 55°
1
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Rainy days

This climate histogram shows you the weather patterns in Hilton Head Island. The warmest months in Hilton Head Island are July and April, when temperatures reach 97 ˚F. The coolest month is December, when temperatures drop to 23 ˚F. The wettest month in Hilton Head Island is January with 8.48 inches of rain, while the driest month is April with 0.76 inches of rain.

What Expert Travelers Think

  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE

Vacation Rentals in Hilton Head Island

Browse accommodations from all the leading providers including Airbnb, RedAwning, Priceline and more at AllTheRooms.com. Hilton Head Island has 21,535 hotels, vacation rentals and other unique places to stay, with prices to suit careful travellers, extravagant travelers and everything in between. In general, a place to stay in Hilton Head Island will cost you $282 per night.

Those needing to get some work finished during their trip to Hilton Head Island can pick from 8,196 places to stay that provide WiFi. We have 82 accommodations that include a breakfast included. Choose from 2,489 places to stay that provide gym options, so you won't miss a single workout. If you're planning on getting to Hilton Head Island by car, be sure to choose from 7,128 accommodations that provide parking. 4,293 accommodations have a a pool or jacuzzi

AllTheRooms has 929 pet-friendly places to stay in Hilton Head Island, so if you're traveling with your cat or dog you won't have any problems.

In Hilton Head Island AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 4 providers, including 4,257 places to stay from Airbnb, 20 accommodations from RedAwning and 20 places to stay from Priceline.

7,707 of the accommodations in Hilton Head Island have been reviewed by previous guests. They rated 27% as excellent or good. You can instantly book any of 8,953 places to stay right now.

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