Hilton Head Island Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Hilton Head Island holiday rentals

A covered outdoor seating area with a view of the sunset over a body of water.

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, (159 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$170
includes taxes & fees
30 Nov - 1 Dec
Marriott's Harbour Point and Sunset Pointe at Shelter Cove
A hotel entrance with a grand staircase, a covered walkway, and a brick-paved area.

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$235
includes taxes & fees
11 Dec - 12 Dec
Marriott's Harbour Club
A beachside resort with a swimming pool, lounge chairs, and a small building, likely a lifeguard station.

3. 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$561
includes taxes & fees
18 Nov - 19 Nov
Steps to the beach! Newly Remodeled! New furniture STR Permit #: 072116
A sandy beach with tall grasses in the foreground and a clear blue sky.

4. Oceanfront Hilton Head Island Condo w/ Pool!

Oceanfront Hilton Head Island Condo w/ Pool!
3.0 star property
South End
8.8 out of 10, Excellent, (6 reviews)
"Nice!! Location great, easy instructions on entry access, nice side view of the ocean from the balcony, the host Meagan was so very nice and accommodating, very close to restaurants and stores, would love to stay here again, Thanks a million!!!! ;)"
United States
Beverly
The price is NZ$532
includes taxes & fees
12 Nov - 13 Nov
Oceanfront Hilton Head Island Condo w/ Pool!
A bedroom with a large bed, a nightstand with a lamp, a dresser, and a window with curtains.

5. Cute Condo close to Coligny Beach

Cute Condo close to Coligny Beach
South End
9.4 out of 10, Exceptional, (26 reviews)
"Would definitely stay there again "
United States
Matilda F.
The price is NZ$301
includes taxes & fees
15 Nov - 16 Nov
Cute Condo close to Coligny Beach
A gated entrance with directional arrows and caution signs.

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
Beach

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

Feelin Tip'Sea-Oceanview Retreat Steps to Beach
South End
9.6 out of 10, Exceptional, (44 reviews)
"You truly are steps to the beach and can see the water from the balcony. This place was so close to shopping and dining. Excellent place to stay!"
United States
Sherri P.
The price is NZ$458
includes taxes & fees
12 Nov - 13 Nov
Feelin Tip'Sea-Oceanview Retreat Steps to Beach
A deck with sun loungers overlooking a natural landscape.

8. 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.
Family Beachfront Retreat: Walk to Coligny Plaza with Side Ocean Views
Beach

9. Coastal Nest - Oceanviews! Near Coligny

Coastal Nest - Oceanviews! Near Coligny
South End
9.6 out of 10, Exceptional, (27 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
Beach

10. Shore To Please! Oceanview couples retreat w/bikes

Shore To Please! Oceanview couples retreat w/bikes
South End
9.8 out of 10, Exceptional, (73 reviews)
"always a pleasant stay"
United States
Christopher R.
Shore To Please! Oceanview couples retreat w/bikes
An aerial view of a resort with multiple buildings, a central swimming pool, and a beach in the background.

11. Marriott's Grande Ocean

Marriott's Grande Ocean
3.5 star property
South End
9.4 out of 10, Exceptional, (180 reviews)
"The property and room was very good. Marriott Service polite and friendly."
United States
Robert Alan
The price is NZ$473
includes taxes & fees
30 Nov - 1 Dec
Marriott's Grande Ocean
A spacious living area with a high ceiling, large windows, and a central seating arrangement.

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$283
includes taxes & fees
2 Dec - 3 Dec
Marriott's Heritage Club
Ahhhhh beach please!

13. Castaways King Villa on Beach, Free Bikes!

Castaways King Villa on Beach, Free Bikes!
South End
10.0 out of 10, Exceptional, (123 reviews)
"Place was on the 1st floor and very convenient location. Pool is a little small but clean. Gate to get in was a little to be desired because it was hard for 2 cars to pass at the same time. Place was clean and host was very easy to deal with and answered any questions for me ASAP. Would stay again. Great for couples."
United States
Kathleen
The price is NZ$477
includes taxes & fees
12 Nov - 13 Nov
Castaways King Villa on Beach, Free Bikes!
A multi-story building with balconies, surrounded by various tropical plants and a clear view of the ocean.

14. 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
Our beautiful beach

15. 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, (185 reviews)
"Perfect for a couple. Great location, very clean and had everything we needed."
United States
Gina C.
Flip Flop Paradise-Steps to the Sand! Free Bikes
A living room with a dining area, a sofa, a coffee table, and a TV.

16. Harbour Town Gem: Serene Lagoon Views & Steps to the Lighthouse

Harbour Town Gem: Serene Lagoon Views & Steps to the Lighthouse
Sea Pines
9.2 out of 10, Wonderful, (219 reviews)
"Very clean and excellent location right around the corner from HarborTown."
United States
Matt K.
The price is NZ$539
includes taxes & fees
15 Nov - 16 Nov
Harbour Town Gem: Serene Lagoon Views & Steps to the Lighthouse
Beach

17. OceanEscape – Steps to the Beach

OceanEscape – Steps to the Beach
South End
9.8 out of 10, Exceptional, (87 reviews)
"Great location. Minutes from so many things. The room was great, super clean, very relaxing. Only advise, rent a bicycle it’s defiantly the way to get around!"
United States
Renee A.
OceanEscape – Steps to the Beach
A balcony with a table set for dining, overlooking a beach and a parking area with a car.

18. Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380

Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380
South End
9.6 out of 10, Exceptional, (109 reviews)
"Awesome spot to stay with everything we needed. Really enjoyed the pool access, walking distance to the beach, and bikes included with the property."
United States
Will K.
The price is NZ$514
includes taxes & fees
15 Nov - 16 Nov
Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380
A wooden boardwalk leading to a beach with palm trees on either side.

19. Resort Breeze-2 BR, Pools, Hot Tub, Tennis, Beach

Resort Breeze-2 BR, Pools, Hot Tub, Tennis, Beach
Mid Island
10.0 out of 10, Exceptional, (20 reviews)
"great stay !"
United States
Sara J.
The price is NZ$533
includes taxes & fees
12 Nov - 13 Nov
Resort Breeze-2 BR, Pools, Hot Tub, Tennis, Beach
A balcony with a view of the ocean, palm trees, and a building with large windows.

20. Elegance at the beach -Ocean View Villa, Gorgeous!

Elegance at the beach -Ocean View Villa, Gorgeous!
South End
10.0 out of 10, Exceptional, (133 reviews)
"Loved our stay!!! Perfect location! Great communication and loved the easy access to the beach and food/shops nearby. Highly recommend!"
United States
Allison A.
Elegance at the beach -Ocean View Villa, Gorgeous!
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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Find holiday rentals that suit your style

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Top Hilton Head Island Hotel Reviews

A modern cafe with exposed ductwork, a brick wall, and large windows.
Drury Plaza Hotel Savannah Pooler

Drury Plaza Hotel Savannah Pooler

Drury Plaza Hotel Savannah Pooler
Pooler

10/10 Excellent

It was great stay. The property was clean. The dinner and popcorn were also very good.
Australia
Ali
Reviewed October 16, 2026
Drury Plaza Hotel Savannah Pooler

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$169 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.

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.

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