Hilton Head Island holiday rentals

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Booking Insights
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Best Hilton Head Island vacation rentals

Direct Oceanfront Villa - Heated Pool & Breathtaking Ocean View - Hilton Head Island - Pool
Parking
Free Wi-Fi
Pool
Air conditioning
Spacious, cozy villa w/parking in Coligny Villas - Hilton Head Island - Bedroom
Parking
Free Wi-Fi
Pool
Air conditioning
Village House 303, 2 Bedrooms, Sleeps 6, - Hilton Head Island - Living room
Village House 303, 2 Bedrooms, Sleeps 6,
Hilton Head Island, SC, United States
Free Wi-Fi
Air conditioning
Marriott's Grande Ocean - Hilton Head Island - Pool
Marriott's Grande Ocean
Hilton Head Island, SC, United States
Pool
Air conditioning
Village House 102 - Hilton Head Island - Living room
Village House 102
Hilton Head Island, SC, United States
Parking
Free Wi-Fi
Pool
Air conditioning
Hilton Head Island Escape - Walk to Beach! - Hilton Head Island - Balcony
Hilton Head Island Escape - Walk to Beach!
Hilton Head Island, SC, United States
Free Wi-Fi
Air conditioning
4102 Windsor Court-Oceanviews And Coastal Inspired - Hilton Head Island - Pool
Free Wi-Fi
Air conditioning
Ocean Front Condo with Private Water Front Balcony - Hilton Head Island
Ocean Front Condo with Private Water Front Balcony
Hilton Head Island, SC, United States
Parking
Free Wi-Fi
Air conditioning
Springwood Villas with pool excess half a mile from beach - Hilton Head Island
Parking
Free Wi-Fi
Pool
Air conditioning
Beachfront Condo w/ Pool Access in Hilton Head! - Hilton Head Island
Beachfront Condo w/ Pool Access in Hilton Head!
Hilton Head Island, SC, United States
Free Wi-Fi
Air conditioning
Booking Insights

KAYAK’s insights for holiday 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 February, with average rates of €161. In comparison, July is the most expensive month, with prices at €1,364.

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

Tuesday offers the lowest rates in Hilton Head Island, with an average nightly price of €175. The highest prices are found on Wednesday, with average rates at €305.

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

Book at least 47 days before your stay begins to get the best price for your Hilton Head Island vacation rental.

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

  • If you’re wanting a good deal then consider staying at the four-star Omni Hilton Head Oceanfront Resort. Included in the price of your stay, you can benefit from free parking and free Wi-Fi, and also access to a variety of pools.
  • Consider staying at Okatie Hilton Head Hotel if you want to be at a short distance from Island West Gold Club. The accommodation is located only a short distance of 1.4 miles from the attraction and offers free breakfast to its guests.
  • Those who are seeking a bit of luxury on their trip to Hilton Head Island should consider staying at the house Beachfront Escape. The house is the optimism of luxury and sleeps up to 12 guests. With four bedrooms and six bathrooms, guests will find themselves near attractions like Tanger Outlet Centre. This accommodation is located directly on the beach and offers a hot tub and free Wi-Fi to its guests.
  • Hilton Head Island Beach is a great visiting attraction for adults and children alike. Those wishing to stay here should consider the Hilton Head Island holiday rental and three-star Holiday Inn Resort Beach House. The accommodation is located 5.4 miles away and is the perfect choice of stay.
  • If you’re visiting Hilton Head Island as a couple then consider staying at the four-star Marriott Hilton Head Resort & Spa. This accommodation has spa facilities on offer and is accommodating to guests seeking a romantic getaway or small break.
  • Kitchen/kitchenette, beachfront, hot tub, pool, pet friendly, and wifi are the most popular holiday rental property amenities in Hilton Head Island
  • Holiday rentals in Hilton Head Island are around 67% more expensive than hotels on average. Search here to compare prices for all accommodation types in Hilton Head Island.
  • The best holiday rental properties in Hilton Head Island are Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown (9.8, 83 reviews), Hilton Head Island Condo w/ Coligny Beach Access! (9.7, 34), and Marriott's Grande Ocean (9.6, 35), based on ratings and reviews from real travellers.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Hilton Head Island for 4 days.

FAQs when booking a holiday home in Hilton Head Island

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

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

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

    If you’re looking for something special, the holiday rental most loved by KAYAK users is Marriott's Surf Watch, A Marriott Vacation Club Resort.

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

    There are a number of dog and pet-friendly Hilton Head Island holiday rentals, with around 5% allowing you to bring your pet along with you.

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

    In the last 72 hours, users have found Hilton Head Island holiday rentals for tonight for as low as €245. Search here for similar prices

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

    In the last 72 hours, users have found Hilton Head Island holiday rentals for this weekend for as low as €148 per night. Search here for similar prices

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

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

  • If I want to stay near Hilton Head Island city centre, where should I stay?

    The Hilton Head Island holiday home, Hilton Head Golfers Getaway Waterfront Location, is the ideal choice of location for those who are wanting to be located only a short distance of 0.6 miles from the city centre of Hilton Head Island. Sleeping up to ten, this house is also equipped with four bedrooms and two bathrooms. Guests will find themselves at a short distance of two miles from attractions like Hudson’s and Skull Creek. It’s the perfect choice of stay, no matter the occasion.

  • Where should I stay if I want to be close to Hilton Head Airport (HHH)?

    The Hilton Island house rental, Brand New & Beautiful #82, is the ideal choice of stay for those wanting to only be at a 0.6-mile distance from the airport. Guests will also be located directly near a movie theatre, shops, and the Sea Turtle Market.

  • Where can I stay if I’m visiting Hilton Head Island in a group?

    Consider staying at the Hilton Head holiday rental, Evian 166 – Two Bedroom Condo, if you’re planning on visiting Hilton Head Island in a group. The condo an accommodate up to six guests and offers two bedrooms and two bathrooms. Guests staying here can also benefit from the free parking and free Wi-Fi available. Guests will find themselves within one mile of attractions like Coligny Beach and Van Der Meer Tennis Academy.

  • If I’m visiting Hilton Head Island on a budget, where should I stay?

    Those who are looking for budget-friendly accommodation at a low price should consider the Hilton Head Island holiday rental and two-star Candlewood Suits Bluffton – Hilton Head. If you’re staying here, then you can also benefit from free parking and also free Wi-Fi.

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 holiday rental.