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$345
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, (25 reviews)
"Absolutely loved our stay would recommend"
United States
xiaoming w.
The price is NZ$483
includes taxes & fees
25 Oct - 26 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.
The price is NZ$451
includes taxes & fees
25 Oct - 26 Oct
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
The price is NZ$460
includes taxes & fees
25 Oct - 26 Oct
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
The price is NZ$452
includes taxes & fees
25 Oct - 26 Oct
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
The price is NZ$469
includes taxes & fees
25 Oct - 26 Oct
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$390
includes taxes & fees
14 Nov - 15 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, (181 reviews)
"Amazing place to vacation. Loved the view. Beach paradise extremely clean, quiet, easy beach access."
United States
Linda P.
The price is NZ$460
includes taxes & fees
25 Oct - 26 Oct
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
The price is NZ$452
includes taxes & fees
25 Oct - 26 Oct
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$601
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)
"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$522
includes taxes & fees
23 Nov - 24 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$422
includes taxes & fees
26 Oct - 27 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, (119 reviews)
"Short, but enjoyable stay. Would stay again!"
United States
Dora D.
The price is NZ$566
includes taxes & fees
1 Nov - 2 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, (89 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.
The price is NZ$471
includes taxes & fees
25 Oct - 26 Oct
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

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.