A coastal town with a lighthouse, marina, and golf course.

Hilton Head Island Holiday Rentals

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Our top choices for Hilton Head Island holiday rentals

1. Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Marriott's Harbour Point and Sunset Pointe at Shelter Cove
3.5 star property
Mid Island
9.2 out of 10, Wonderful, (157 reviews)
"It was a very nice vacation club. They had activities planned throughout the day that you could attend if you’d like. My kids really enjoyed themselves."
United States
Gary T
The price is NZ$246
includes taxes & fees
19 Nov - 20 Nov
Marriott's Harbour Point and Sunset Pointe at Shelter Cove

2. Marriott's Harbour Club

Marriott's Harbour Club
3.5 star property
Sea Pines
9.0 out of 10, Wonderful, (64 reviews)
"We are vacation club owner and we extended our stay with Hotels.com Harbor Club is our favorite property on HHI. "
United States
Mark
The price is NZ$277
includes taxes & fees
8 Nov - 9 Nov
Marriott's Harbour Club

3. Seas the Day! Beach & Sun, with Bikes & Chairs

Seas the Day! Beach & Sun, with Bikes & Chairs
South End
9.6 out of 10, Exceptional, (40 reviews)
"Great Stay."
United States
Robert
Seas the Day! Beach & Sun, with Bikes & Chairs

4. Beachfront Condo w/ Pool Access in Hilton Head!

Beachfront Condo w/ Pool Access in Hilton Head!
South End
9.2 out of 10, Wonderful, (94 reviews)
"Great stay"
United States
Matt H.
The price is NZ$676
includes taxes & fees
26 Oct - 27 Oct
Beachfront Condo w/ Pool Access in Hilton Head!

5. SeaClusion-Oceanview, Mini split AC, Beach Chairs

SeaClusion-Oceanview, Mini split AC, Beach Chairs
South End
9.6 out of 10, Exceptional, (85 reviews)
"We had a great stay. We love the location, close to everything. My family loved staying here and we can't wait to come back."
United States
Michael C.
SeaClusion-Oceanview, Mini split AC, Beach Chairs

6. Fresh Coastal Retreat with Ocean Views | Bikes Incl.

Fresh Coastal Retreat with Ocean Views | Bikes Incl.
South End
9.6 out of 10, Exceptional, (16 reviews)
"Beautiful view, clean, and great communication"
United States
Crystal H.
Fresh Coastal Retreat with Ocean Views | Bikes Incl.

7. Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views
South End
9.4 out of 10, Exceptional, (87 reviews)
"This condo has a nice view, but that's about all it has going for it. It's very small...I think it would be too crowded for more than 2 people. It was adequately furnished, but the sofa, chair, and footstools were badly stained. The bed was comfy, but there was a bad odor in the apt. The property management company was pleasant to deal with."
United States
Patsy
The price is NZ$548
includes taxes & fees
2 Nov - 3 Nov
Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

8. Coastal Nest - Oceanviews! Near Coligny

Coastal Nest - Oceanviews! Near Coligny
South End
9.4 out of 10, Exceptional, (24 reviews)
"This place was a great stay! It was as close to the beach as advertised. A couple minute walk if that. The location was near lots of restaurants and shops. Parking was easy. The host communicated very well. We had no issues!"
United States
Ellie
Coastal Nest - Oceanviews! Near Coligny

9. At beach. No price increase! Also #5406326 renovated, #2320603 panoramic view.

At beach. No price increase! Also #5406326 renovated, #2320603 panoramic view.
Mid Island
10.0 out of 10, Exceptional, (155 reviews)
"Cozy condo that was perfect for our stay."
United States
Shawn K.
The price is NZ$463
includes taxes & fees
31 Oct - 1 Nov
At beach. No price increase! Also #5406326 renovated, #2320603 panoramic view.

10. Castaways King Villa on Beach, Free Bikes!

Castaways King Villa on Beach, Free Bikes!
South End
10.0 out of 10, Exceptional, (122 reviews)
"Great place to stay, we will be back for another stay."
United States
Kopitar Kings 1.
Castaways King Villa on Beach, Free Bikes!

11. Marriott's Monarch at Sea Pines

Marriott's Monarch at Sea Pines
3.0 star property
Sea Pines
9.2 out of 10, Wonderful, (132 reviews)
"Loved this property "
United States
Sharon
The price is NZ$341
includes taxes & fees
19 Nov - 20 Nov
Marriott's Monarch at Sea Pines

12. Marriott's Heritage Club

Marriott's Heritage Club
3.5 star property
Sea Pines
9.4 out of 10, Exceptional, (71 reviews)
"Great Villa! Very roomy and excellent location close to everything!"
United States
Christine
The price is NZ$316
includes taxes & fees
5 Nov - 6 Nov
Marriott's Heritage Club

13. SunnyDaze-Brand new reno- King bed, Free bikes!

SunnyDaze-Brand new reno- King bed, Free bikes!
South End
9.6 out of 10, Exceptional, (112 reviews)
"Great place to stay!"
United States
Jake H.
SunnyDaze-Brand new reno- King bed, Free bikes!

14. Coligny Beach, Pools, & Shops- Few Steps Away

Coligny Beach, Pools, & Shops- Few Steps Away
South End
9.6 out of 10, Exceptional, (98 reviews)
"Great Location. Was very clean and accommodating."
United States
Cheryl M.
The price is NZ$627
includes taxes & fees
2 Nov - 3 Nov
Coligny Beach, Pools, & Shops- Few Steps Away

15. Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116

Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116
Mid Island
9.6 out of 10, Exceptional, (119 reviews)
"Short, but enjoyable stay. Would stay again!"
United States
Dora D.
The price is NZ$568
includes taxes & fees
1 Nov - 2 Nov
Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116

16. Shore Beats Work!-Stunning view 3 from oceanfront new bikes Incl.

Shore Beats Work!-Stunning view 3 from oceanfront new bikes Incl.
South End
9.4 out of 10, Exceptional, (65 reviews)
"The room has a good view of the ocean and the hosts were great!"
United States
Matt W.
Shore Beats Work!-Stunning view 3 from oceanfront new bikes Incl.

17. Beachfront Condo w/ Pool Access in Hilton Head!

Beachfront Condo w/ Pool Access in Hilton Head!
4.0 star property
South End
8.0 out of 10, Very good, (3 reviews)
"The security guard was friendly. The condo was clean. I am not sure if all of these were from the host or left behind but there was a coffee maker, spice rack (which I’ve never seen in a condo before), dishwasher, plenty of pots and pans, not a lot of utensils for cooking, a hair dryer, small tin of coffee creamer, pool towel (clean), extra blankets (clean), a single trash bag for the kitchen, paper towels, kitchen towel, chairs and beach things on the deck. It was on the beach just have to walk...
United States
Manuel
Beachfront Condo w/ Pool Access in Hilton Head!

18. Coastal Getaway: Oceanview Condo in Hilton Head

Coastal Getaway: Oceanview Condo in Hilton Head
South End
9.6 out of 10, Exceptional, (25 reviews)
"The perfect stay for us. Beach was easily accessible, condo was well cleaned, and host was very easy to contact. Would recommend!"
United States
Samantha K.
Coastal Getaway: Oceanview Condo in Hilton Head

19. Just Beachy! Absolute top notch design, Oceanviews

Just Beachy! Absolute top notch design, Oceanviews
South End
9.8 out of 10, Exceptional, (48 reviews)
"Great communication and smooth check-in process! Convenient location and easy access to the beach!"
United States
Casey B.
Just Beachy! Absolute top notch design, Oceanviews

20. True Oceanfront Last Min Oct22 10Nts S990 ALL IN Price!

True Oceanfront Last Min Oct22 10Nts S990 ALL IN Price!
South End
9.8 out of 10, Exceptional, (144 reviews)
"Great location! Everything went as expected. Thank you!"
United States
Jennifer S.
The price is NZ$635
includes taxes & fees
31 Oct - 1 Nov
True Oceanfront Last Min Oct22 10Nts S990 ALL IN Price!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hilton Head Island Hotel Reviews

Find out more about Hilton Head Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Hilton Head Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Hilton Head Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Hilton Head Island. Seeing all the best attractions is bound to make you fall in love with Hilton Head Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Hilton Head Island short-term rentals, that won’t be hard to do.

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Frequently asked questions

Are there holiday rentals in Hilton Head Island?

Yes, there are holiday rentals in Hilton Head Island close to The Sandbox, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the scenic seaside and waterfront in Hilton Head Island. Make sure you have time to check out the golf courses while you're in the area.

What are some of the best holiday rentals that Hilton Head Island has to offer?

New Four BR Luxury Vacation Home on Hilton Head: This highly rated holiday home rental in Hilton Head Island has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a microwave, so that you can cook with friends or family. Other favourite homes for rent in Hilton Head Island are Palmetto Dunes, pool, hot tub, walk to beach, dog friendly, bikes, sleeps 15 and Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380.

How many holiday rentals are there in Hilton Head Island?

With 986 Expedia holiday rentals, you're guaranteed to find just the right place for your Hilton Head Island stay.

What’s there to see and do in Hilton Head Island?

Cultural attractions include Arts Center of Coastal Carolina and Coastal Discovery Museum, whereas Sea Pines Forest Preserve and Coligny Beach are a couple of picturesque spots to enjoy the outdoors. Marine Corps Recruit Depot Parris Island and River Street are other popular places to visit in the area.

What’s a holiday rental in Hilton Head Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hilton Head Island. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.