Hilton Head Island holiday homes and lettings - HomeToGo base64Hash Hilton Head Island holiday homes and lettings - HomeToGo

Hilton Head Island holiday homes and lettings

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Top 15 Recommended holiday lettings in Hilton Head Island

Find your perfect holiday home, apartment or cottage in Hilton Head Island from just £147 per night!

Condo Hilton Head Island
Condo ∙ 10 guests ∙ 3 bedrooms

Flat with pool & hot tub | Nature view | Beach nearby

Hilton Head Island, Beaufort County, South Carolina, United States
from £255
per night
Outstanding(39 ratings)
from £255
per night
View deal
House Hilton Head Island
House ∙ 14 guests ∙ 6 bedrooms

Child-friendly holiday home with barbeque, terrace & private pool | Perfect for remote work

Hilton Head Island, Beaufort County, South Carolina, United States
from £309
per night
Outstanding(30 ratings)
from £309
per night
View deal
House Hilton Head Island
House ∙ 12 guests ∙ 4 bedrooms

House with terrace, barbecue & garden | Suitable for remote work

Hilton Head Island, Beaufort County, South Carolina, United States
from £368
per night
Very good(1 rating)
from £368
per night
View deal
House Hilton Head Island
House ∙ 12 guests ∙ 5 bedrooms

House with BBQ, private pool & terrace

Hilton Head Island, Beaufort County, South Carolina, United States
from £330
per night
Outstanding(102 ratings)
from £330
per night
View deal
House Hilton Head Island
House ∙ 24 guests ∙ 7 bedrooms

Family-friendly holiday home with private pool, terrace & barbecue | Pets allowed

Hilton Head Island, Beaufort County, South Carolina, United States
from £447
per night
Very good(115 ratings)
from £447
per night
View deal
House Hilton Head Island
House ∙ 11 guests ∙ 4 bedrooms

Holiday home with terrace, private pool & BBQ | Nature view

Hilton Head Island, Beaufort County, South Carolina, United States
from £559
per night
Outstanding(68 ratings)
from £559
per night
View deal
House Hilton Head Island
House ∙ 10 guests ∙ 3 bedrooms

Holiday home with terrace, jacuzzi & barbeque

Hilton Head Island, Beaufort County, South Carolina, United States
from £354
per night
Outstanding(27 ratings)
from £354
per night
View deal
House Hilton Head Island
House ∙ 12 guests ∙ 5 bedrooms

Children-friendly holiday home with barbeque, jacuzzi & private pool | Next to the beach

Hilton Head Island, Beaufort County, South Carolina, United States
from £454
per night
Outstanding(13 ratings)
from £454
per night
View deal
House Hilton Head Island
House ∙ 12 guests ∙ 5 bedrooms

Family-oriented house with private pool, hot tub & terrace | Close to the beach | Perfect for remote work | Pets allowed

Hilton Head Island, Beaufort County, South Carolina, United States
from £425
per night
Outstanding(109 ratings)
from £425
per night
View deal
House Hilton Head Island
House ∙ 12 guests ∙ 4 bedrooms

House with private pool, hot tub & barbeque

Hilton Head Island, Beaufort County, South Carolina, United States
from £485
per night
Outstanding(32 ratings)
from £485
per night
View deal
House Hilton Head Island
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped lovely holiday home with terrace, private pool & barbecue | Dogs allowed

Hilton Head Island, Beaufort County, South Carolina, United States
from £218
per night
Very good(107 ratings)
from £218
per night
View deal
House Hilton Head Island
House ∙ 12 guests ∙ 6 bedrooms

Family-friendly holiday home with terrace, jacuzzi & private pool | Good for workation

Hilton Head Island, Beaufort County, South Carolina, United States
from £409
per night
Excellent(31 ratings)
from £409
per night
View deal
House Hilton Head Island
House ∙ 12 guests ∙ 5 bedrooms

Fully equipped holiday home with barbeque, private pool & terrace | Nature view | Close to the beach | Good for workation

Hilton Head Island, Beaufort County, South Carolina, United States
from £675
per night
Excellent(44 ratings)
from £675
per night
View deal
House Hilton Head Island
House ∙ 10 guests ∙ 4 bedrooms

House with terrace, hot tub & barbecue | Nature view

Hilton Head Island, Beaufort County, South Carolina, United States
from £541
per night
Outstanding(59 ratings)
from £541
per night
View deal
House Hilton Head Island
House ∙ 11 guests ∙ 4 bedrooms

Holiday home with garden, terrace & private pool

Hilton Head Island, Beaufort County, South Carolina, United States
from £278
per night
Outstanding(91 ratings)
from £278
per night
View deal

Most popular holiday lettings with a fireplace

House  Hilton Head Island
from £191 per night
House ∙ 10 guests ∙ 4 bedrooms

Child-friendly nice holiday home with terrace, private pool & BBQ | Nature view | Pets are welcome

4.2
Very good(65 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
Fireplace
View deal
House  Hilton Head Island
from £252 per night
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly wonderful holiday home with barbeque, pool & terrace | Nature view | Perfect for remote work

5.0
Outstanding(38 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
Fireplace
View deal
House  Hilton Head Island
from £155 per night
House ∙ 8 guests ∙ 3 bedrooms

House with terrace, barbeque & private pool

4.0
Very good(45 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
Fireplace
View deal
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Holiday lettings and apartments with air conditioning

House  Hilton Head Island
from £346 per night
House ∙ 14 guests ∙ 5 bedrooms

Fully equipped house with terrace, garden & jacuzzi | Close to the beach

Hilton Head Island, Beaufort County, South Carolina, United States
Air conditioning
View deal
House  Hilton Head Island
from £247 per night
House ∙ 15 guests ∙ 5 bedrooms

Children-friendly house with private pool, BBQ & terrace

5.0
Outstanding(58 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
Air conditioning
View deal
House  Hilton Head Island
from £1,299 per night
House ∙ 26 guests ∙ 8 bedrooms

Holiday home with jacuzzi, terrace & barbeque | Lake view | Good for workation

5.0
Outstanding(36 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
Air conditioning
View deal
See all offers

Best holiday homes with a patio or terrace

House  Hilton Head Island
from £224 per night
House ∙ 10 guests ∙ 3 bedrooms

House with private pool, terrace & BBQ | Perfect for remote work

5.0
Outstanding(2 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
Balcony/Patio
View deal
House  Hilton Head Island
from £227 per night
House ∙ 14 guests ∙ 5 bedrooms

House with terrace, barbecue & private pool | Nature view

4.5
Excellent(64 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
Balcony/Patio
View deal
House  Hilton Head Island
from £289 per night
House ∙ 12 guests ∙ 5 bedrooms

Family-friendly house with pool & barbecue | Next to the beach

4.0
Very good(1 rating)
Hilton Head Island, Beaufort County, South Carolina, United States
Balcony/Patio
View deal
See all offers

Budget-friendly Holiday Homes in Hilton Head Island

Find Fantastic yet Cheap Lettings

House Hilton Head Island
from £541 per night
House ∙ 13 guests ∙ 5 bedrooms

Fully equipped charming house with hot tub, private pool & barbecue | Next to the beach | Good for workation

4.8
Outstanding(26 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal
House Hilton Head Island
from £209 per night
House ∙ 15 guests ∙ 5 bedrooms

Family-friendly big house with terrace, private pool & barbecue | Nature view | Pets are welcome

4.6
Excellent(46 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal
House Hilton Head Island
from £477 per night
House ∙ 14 guests ∙ 6 bedrooms

Fully equipped house with barbeque, private pool & terrace | Beach nearby

4.5
Excellent(17 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal

Top-Rated Lettings and Properties in Hilton Head Island

Book Holiday Letting Offers with the Highest User Rating

House Hilton Head Island
from £349 per night
House ∙ 12 guests ∙ 4 bedrooms

Family-oriented pleasant house with terrace, private pool & barbeque | Good for workation | Pet-friendly

5.0
Outstanding(78 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal
House Hilton Head Island
from £261 per night
House ∙ 11 guests ∙ 3 bedrooms

Fully equipped holiday home with terrace, barbeque & private pool | Nature view

4.9
Outstanding(64 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal
Villa Hilton Head Island
from £214 per night
Villa ∙ 8 guests ∙ 3 bedrooms

Villa with barbeque, terrace & pool

5.0
Outstanding(60 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal

Customer ratings and reviews

How are reviews collected?
Darlene W.
Guest verified by HomeToGo

The home was clean and a great location. Although the bed was a little to firm for my liking, our overall stay was delightful.

Reviewed on 19/03/2025
Villa Hilton Head Island
from £168 per night
HomeToGo
Villa ∙ 8 guests ∙ 2 bedrooms
5.0
Outstanding(19 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal
John W.
Guest verified by HomeToGo

We did enjoy our stay and loved the location of the house. Close to bike rentals & restaurants. The den & wifi were wonderful as well as the washer & dryer! Loved exploring HH Island The house could use some TLC sliding glass doors/screen hard to open; kitchen pots/pans tough shape and mattresses were not very comfortable for a stay over a week. Overall, the house was very cute, nicely decorated & in a great location.

Reviewed on 01/03/2025 | Family
House Hilton Head Island
from £225 per night
HomeToGo
House ∙ 8 guests ∙ 3 bedrooms
4.5
Excellent(2 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal
Tom G.
Guest verified by HomeToGo

House very spacious, good location on back side of island. Prompt and clear communication. A few maintenance projects needed.

Reviewed on 20/02/2025 | Couple
House Hilton Head Island
from £208 per night
HomeToGo
House ∙ 8 guests ∙ 3 bedrooms
4.2
Very good(78 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal
Calvin C.
Guest verified by HomeToGo

We loved our stay at this beautiful vacation rental. The location is perfect for the shops and restaurants at Shelter Cove Marina. The property manager, Tricia was so easy to communicate with and answered all our questions quickly. The condo itself was updated and although we did not cook, the kitchen was fully outfitted. The beds were comfy and the master shower was great! The little porch was nice if you wanted to sit outside and get some fresh air. The beach access was an easy drive (pretty far to walk) and our pup loved chasing balls on the beautiful wide beach. Our only issue was the master bedroom tv lost interest access one evening and would not work. I had to reset the router the next morning which solved the issue. You do have to be a little tech savvy to work the tvs. We would definitely stay here again. Can’t wait to come back!

Reviewed on 16/11/2024 | Couple
Apartment Hilton Head Island
from £129 per night
HomeToGo
Apartment ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding(44 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal
Nell H.
Guest verified by HomeToGo

The home was nicely decorated and well equipped for cooking. The bed was most comfortable. The wifi was great. Unfortunately, the coolness of the weather did not allow us to enjoy the romantic patio setting.

Reviewed on 29/10/2024 | Couple
Condo Hilton Head Island
from £96 per night
HomeToGo
Condo ∙ 4 guests ∙ 1 bedroom
4.0
Very good(11 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal
Jeff M.
Guest verified by HomeToGo

Unit 903 was actually in Ship Master within the community of Shipyard. Was a very nice stay and management was very communicative quickly. Our personal preference was to have walk-in showers and this unit only had bathtubs. They had two coffee pots which took care of pods or filters so that was really nice.

Reviewed on 02/09/2024 | Couple
Villa Hilton Head Island
from £109 per night
HomeToGo
Villa ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(50 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal
Rosemary S.
Guest verified by HomeToGo

The home was clean, comfortable and very well equipped with everything we needed for our yearly vacation to HHI. Furnishings were new and not beaten down like some vacation rentals.

Reviewed on 26/08/2024 | Family
House Hilton Head Island
from £506 per night
HomeToGo
House ∙ 25 guests ∙ 6 bedrooms
5.0
Outstanding(10 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal
Brian P.
Guest verified by HomeToGo

Had everything we needed. This was our second time in this home, will definitely be back. Plenty of room for a family of 8.

Reviewed on 17/06/2024 | Family
House Hilton Head Island
from £443 per night
HomeToGo
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding(24 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal
Jennifer C.
Guest verified by HomeToGo

A large enough space for everyone to spread out and do their own thing but still able to gather all in on area for games and meals. The decor was very nice but the light fabrics kept me tense with small children.

Reviewed on 22/05/2024 | Family
House Hilton Head Island
from £343 per night
HomeToGo
House ∙ 13 guests ∙ 5 bedrooms
5.0
Outstanding(6 ratings)
Hilton Head Island, Beaufort County, South Carolina, United States
View deal
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Trust in the quality and comfort of your stay with verified guest reviews.

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Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform holiday planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in Hilton Head Island

  • Pool (12,693)
  • WiFi (13,349)
  • Parking (1,093)
  • TV (13,538)
  • Air conditioning (14,018)
  • Balcony/patio (6,188)
  • Kitchen (13,656)
  • Washing machine (11,367)
  • Grill (7,440)
  • No pets (12,208)
  • Garden (2,157)
  • Hot tub (3,239)

You will have a lot of holiday lettings from which to choose if you are looking for a letting offering a pool in Hilton Head Island. More condo include a pool than apartment rental. Typically, condo with pools in Hilton Head Island accommodate 6 people and cost £413 a night. Nearly half of Hilton Head Island's properties including a pool are located within 2 kilometres of water, so you can choose between some pool time or waterfront moments.

Price and Availability Index for Hilton Head Island

Click on any bar to see price and availability information

Holiday Letting Price Information in Hilton Head Island

We analysed price data and summarised our findings in this graph, which shows holiday accommodation prices for the upcoming months in Hilton Head Island. The most expensive month in Hilton Head Island is June (13/06 – 20/06), when average prices are £410 a night. Conversely, the cheapest average prices are in one week of October (25/10 – 01/11).

Rental availability information in Hilton Head Island

Check out the graph above to find out how many holiday rentals are available in Hilton Head Island (in %). It is harder to find accommodation during the week of January (10/01 – 17/01), as 81% of the rentals are booked. It will be easy to find a holiday home that suits you in one week in September (06/09 – 13/09), when 69 of the rentals are still available.

Discover Hilton Head Island with your own luxury holiday accommodation

Voted the number one island on the continent, Hilton Head Island holiday accommodation offers you an unforgettable experience with beautiful beach front cottages or stylish apartments. Whether it's world class tennis or top golf courses you're after, Hilton Head has you covered. Supreme dining experiences and a rich natural heritage are yours when you book holiday accommodation on Hilton Head Island.

What are the best activities for families in Hilton Head Island?

Family holidays on Hilton Head Island

The island'sinteractive kids' museum is specially designed for little people, with a thrilling range of exhibits that will delight and stimulate them. They'll discover perfect play places, aquariums and a room that blends sound with colour. For the little engineers, there are Builders of Tomorrow, while future pilots will love the Flight Deck. Programs like Imagination Hour and Leap into Learning Wednesdays bring the community together to learn through play.

What are the must-see attractions in Hilton Head Island?

Highlights of Hilton Head

Coastal Discovery Museum

When you visit this museum, you will be immersed in the ecology of the South Carolina coast. Discover natural history and cultural heritage all in one place as you explore 68 acres filled with oaks, marshes, and gardens. Meet alligators at live demonstrations and enter the butterfly enclosure to see these insects in full flutter.

Pinckney Island National Wildlife Reserve

Over 250 species inhabit this diverse landscape. Songbirds warble in the branches of the scrub, red foxes, and bobcats dart silently through the bushes, and raptors cruise overhead. Follow the trails through this natural paradise, where learning and exploration cross paths.

Harbour Town Light

This lighthouse houses a remarkable collection of artwork, antique golf memorabilia, vintage apparel, and automobiles. You'll also find classic games here, clocks, and timekeepers, and a library of historic books that you'll want to pore over for hours.

Arts Centre of Coastal Carolina

There's always an exciting performance happening at Hilton Head's vibrant Arts Centre. Whether you're a jazz enthusiast, a musical fanatic or you have a passion for contemporary dance, there's something for everyone. What's more, enthralling contemporary art exhibits fill the gallery space in the Bank of America Room and Walter Greer Gallery.

Harbour Town Golf Links

This course requires finesse, creativity, and precision as opposed to strength, and its various par threes rank among the best in the world. Harbour Town's par four 18th hole is one of the most feared in the golfing world. Constant enhancements to the course provide you with a premium game.

Information about holiday rentals in Hilton Head Island

🏡 Holiday homes available 14,281 rentals
💳 Discounts available up to 13%
🌙 Nightly prices from £147
⭐ Popular amenities Pool, Internet and Parking
🐾 Pet friendly rentals 2,101 properties
🏊 Holiday rentals with pools 12,675 properties
52 reviews
Hilton Head Island holiday rentals have an average rating of 4.3/5 across 52 reviews left by travellers.

Frequently Asked Questions

What is a common nightly price for a holiday rental in Hilton Head Island?

Nightly rates for holiday rentals in Hilton Head Island start from around £147. Rates will depend on location, property size, and extras like a pool or pet-friendly access. Check HomeToGo to see current rates and discounts.

How many holiday cottages are available to rent in Hilton Head Island? And what are the most popular types of holiday lets?

Currently there are 14,281 holiday lettings from 33 providers on offer in Hilton Head Island. Nearly half of holiday rentals in Hilton Head Island are condos, making them a top pick among travellers. These properties are perfect for families, couples, or groups looking for a cosy base. Find your perfect match on HomeToGo today.

What is the most searched holiday rental amenity in Hilton Head Island?

Three most popular holiday rental amenities among our customers in Hilton Head Island are Pool, Internet and Parking.

Do you offer holiday homes with a swimming pool in Hilton Head Island?

Looking for a pool? You’ll find that nearly half of holiday cottages and homes in Hilton Head Island have one. Whether you’re travelling with kids or just want a splash, you’re sorted with 12,675 options available. Use HomeToGo to browse offers with pools and book your dream holiday rental!

What's the perfect time to travel to Hilton Head Island?

Book your Hilton Head Island holiday in October or November to avoid a washout; these are the months with the least amount of rain.

Can you get deals on holiday lettings in Hilton Head Island?

You can find brilliant bargains on holiday lets in Hilton Head Island with prices for a let starting at just £147 - and HomeToGo has introduced plenty of filters that mean it's quick and simple to uncover some awesome deals. When considering different dates for a trip, search with HomeToGo's flexible dates technology to easily look for low-price timings and see discounts of up to 13%. Additionally, HomeToGo's 'distance from' filter enables you to discover hidden gem holiday homes in lower-price, lesser-known locales that are just as close to the area of your choice, whether that's the coastline, a swimming lake, winter sports area or town centre. Start searching with time to spare to get the best of the greatest variety of options and low prices - and do so with confidence by using HomeToGo's 'free cancellation' filter when you search.

What are the advantages of booking a holiday rental in Hilton Head Island with HomeToGo?

From serenity away from the crowds to more space for relaxing with your family, friends or partner, holiday rentals in Hilton Head Island bring plenty of benefits. HomeToGo surfaces real reviews written by previous guests, and searching is secure, easy, and stress-free - so with 14,281 rentals from 33 providers in the region, you're bound to uncover the perfect type of accommodation with all of the amenities to suit you in Hilton Head Island.

Do you offer holiday accommodation for couples in Hilton Head Island?

Yes, there are many romantic holiday rentals in Hilton Head Island perfect for two. Enjoy a romantic retreat with just the right amount of space and charm. Let HomeToGo help you plan your next romantic break.

Can I book a waterfront holiday rental in Hilton Head Island?

Absolutely! You’ll find 14230 holiday rentals close to lakes, rivers or the sea in Hilton Head Island. They're great for beach lovers or anyone seeking a peaceful retreat by the water. Book with HomeToGo for a stay just steps from the water.

Why should I book my holiday rental with HomeToGo?

HomeToGo brings together over 15 million holiday rentals from trusted providers, so you can find the best deal in one place. Our smart search makes it easy to find what suits you. Book with confidence and enjoy support every step of the way.

Can I find family-friendly holiday lettings in Hilton Head Island?

Yes, there are lots of family-friendly holiday homes in Hilton Head Island. You’ll find options for every budget and family size. Use HomeToGo to explore family-friendly holiday cottages with ease.

Can I cancel my holiday rental booking for free?

Worried about changes? Plenty of holiday rentals listed on HomeToGo come with free cancellation options. Just make sure to check the property's policy before booking.

Is it possible to rent a holiday home for a weekend getaway in Hilton Head Island?

Short stays are absolutely possible in Hilton Head Island, including weekends. Many homes offer short stays without long commitments. Discover your ideal holiday home with ease on HomeToGo.

Are there any last-minute holiday rental deals in Hilton Head Island?

Need a quick break? Last-minute holiday is just a few clicks away in Hilton Head Island. With HomeToGo, you can find great value — and save up to 13%, even at short notice. Check often and book quickly to grab the best offers.

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