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 Monarch at Sea Pines

Marriott's Monarch at Sea Pines
3.0 star property
Sea Pines
9.2 out of 10, Wonderful, (133 reviews)
"After a booking mixup on what Expedia had listed & what the property details were.. we were happily surprised that the staff & GM made an exception for our reservation. Everyone was very helpful, room was great, clean, great outdoor spaces & easy beach access."
United States
Cory
The price is NZ$336
includes taxes & fees
20 Nov - 21 Nov
Marriott's Monarch at Sea Pines

2. 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$276
includes taxes & fees
19 Nov - 20 Nov
Marriott's Heritage Club

3. STUNNING ocean view! Brand new listing

STUNNING ocean view! Brand new listing
South End
9.8 out of 10, Exceptional, (26 reviews)
"Absolutely loved our stay would recommend"
United States
xiaoming w.
The price is NZ$463
includes taxes & fees
27 Oct - 28 Oct
STUNNING ocean view! Brand new listing

4. Feelin Tip'Sea-Oceanview Retreat Steps to Beach

Feelin Tip'Sea-Oceanview Retreat Steps to Beach
South End
9.6 out of 10, Exceptional, (43 reviews)
"Great trip, great host"
United States
Carter K.
Feelin Tip'Sea-Oceanview Retreat Steps to Beach

5. Beach Daze-Gorgeous new shower! Bikes Included

Beach Daze-Gorgeous new shower! Bikes Included
South End
9.8 out of 10, Exceptional, (31 reviews)
"Excellent location! The place was so close to the beach & walking/biking distance to shops and restaurants."
United States
Kathleen
Beach Daze-Gorgeous new shower! Bikes Included

6. 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

7. Crashin' Waves-Oceanview w/new bikes, Chairs& King Bed

Crashin' Waves-Oceanview w/new bikes, Chairs& King Bed
South End
9.6 out of 10, Exceptional, (190 reviews)
"Loved the bikes and location to everything. We were comfortable and had all we needed for the beach too."
United States
Margaret
Crashin' Waves-Oceanview w/new bikes, Chairs& King Bed

8. SeaGem-Oceanview! Steps to ocean Many Upgrades New Reno

SeaGem-Oceanview! Steps to ocean Many Upgrades New Reno
South End
9.8 out of 10, Exceptional, (108 reviews)
"Kendall's place was comfortable, clean and just as described. The location was great and easy to find. We will definitely stay here again."
United States
Beth T.
SeaGem-Oceanview! Steps to ocean Many Upgrades New Reno

9. 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

10. 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.
Beachfront Condo w/ Pool Access in Hilton Head!

11. Marriott's SurfWatch

Marriott's SurfWatch
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (202 reviews)
"Great resort, great room "
United States
Crista
The price is NZ$542
includes taxes & fees
17 Nov - 18 Nov
Marriott's SurfWatch

12. 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$276
includes taxes & fees
3 Nov - 4 Nov
Marriott's Harbour Club

13. Flip Flop Paradise-Steps to the Sand! Free Bikes

Flip Flop Paradise-Steps to the Sand! Free Bikes
South End
9.8 out of 10, Exceptional, (182 reviews)
"Amazing place to vacation. Loved the view. Beach paradise extremely clean, quiet, easy beach access."
United States
Linda P.
Flip Flop Paradise-Steps to the Sand! Free Bikes

14. Seabatical-Beautiful ocean view! w/new bikes & Chairs

Seabatical-Beautiful ocean view! w/new bikes & Chairs
South End
10.0 out of 10, Exceptional, (95 reviews)
"The room was perfect myself and my cousin. We loved how the room was right on the beach. We also enjoyed the bikes, beach chairs, toys and how close it was to Coligny beach park. Would definitely stay here again."
United States
Raven
Seabatical-Beautiful ocean view! w/new bikes & Chairs

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

Coligny Beach, Pools, & Shops- Few Steps Away
South End
9.6 out of 10, Exceptional, (98 reviews)
"The place is immaculate and the location is excellent."
United States
Margarita
The price is NZ$622
includes taxes & fees
23 Nov - 24 Nov
Coligny Beach, Pools, & Shops- Few Steps Away

16. OceanEscape – Steps to the Beach

OceanEscape – Steps to the Beach
South End
9.8 out of 10, Exceptional, (87 reviews)
"Great location!"
United States
Alycia R.
OceanEscape – Steps to the Beach

17. 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)
"Everything was perfect from location, cleanliness, and communication with the host"
United States
Victor A.
The price is NZ$513
includes taxes & fees
2 Nov - 3 Nov
Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views

18. 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$417
includes taxes & fees
27 Oct - 28 Oct
At beach. No price increase! Also #5406326 renovated, #2320603 panoramic view.

19. 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, (120 reviews)
"Short, but enjoyable stay. Would stay again!"
United States
Dora D.
The price is NZ$583
includes taxes & fees
25 Nov - 26 Nov
Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116

20. Good Times and Tan Lines!-Central air, free bikes!

Good Times and Tan Lines!-Central air, free bikes!
South End
9.8 out of 10, Exceptional, (91 reviews)
"Such a great experience! This condo is directly on the beach and the hosts were excellent! We would definitely stay here again!"
United States
Valerie G.
Good Times and Tan Lines!-Central air, free bikes!
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

Everything you need to know about Hilton Head Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hilton Head Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hilton Head Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hilton Head Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hilton Head Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hilton Head Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hilton Head Island holiday rentals we have selected for you start as low as NZ$245 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hilton Head Island rentals

At Expedia, we put the best Hilton Head Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hilton Head Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hilton Head Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hilton Head Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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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.