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

Hilton Head Island Vacation Rentals

Q: What are some of the best vacation rentals that Hilton Head Island has to offer?

New Four BR Luxury Vacation Home on Hilton Head : Visitors give good reviews to this Hilton Head Island vacation home rental, which 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 you can cook with friends or family. Other favorite 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 .

Dates

November 2026

December 2026

Bundle & Save
Get more, spend less whenever you see Bundle & Save deals
OneKeyCash
Earn OneKeyCash on all your eligible bookings
Upfront pricing
We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Hilton Head Island vacation 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

Mid Island

Gary T

$87 nightly

Nov 30 - Dec 1

Total with taxes and fees

A hotel entrance with a grand staircase, a covered walkway, and a brick-paved area.

2. Marriott's Harbour Club

Sea Pines

Mark

$111 nightly

Dec 9 - Dec 10

Total with taxes and fees

A compact living space with a kitchenette, a sofa, a coffee table, and a balcony with a view.

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

South End

Sherri P.

$231 nightly

Nov 10 - Nov 11

Total with taxes and fees

A beachside resort with a swimming pool, lounge chairs, and a small building, likely a lifeguard station.

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

Mid Island

Dora D.

$280 nightly

Nov 18 - Nov 19

Total with taxes and fees

A multi-story building with balconies, surrounded by various tropical plants and a clear view of the ocean.

5. Beach Daze-Gorgeous new shower! Bikes Included

South End

Kathleen

$234 nightly

Nov 10 - Nov 11

Total with taxes and fees

A view of a beach with a parking lot and buildings in the foreground.

6. Castaways King Villa on Beach, Free Bikes!

South End

Kathleen

$240 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

South End

Gina C.

$234 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern kitchen with white cabinets, a dining area with a table and chairs, a sofa, and a ceiling fan.

8. Beachy Keen Seaside Villa Near Coligny W/Bikes!

South End

Katleen M.

$231 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

South End

Jake H.

$233 nightly

Nov 10 - Nov 11

Total with taxes and fees

A cozy living area with a wooden table, a sofa, and a kitchen in the background.

10. Totally Beachin' Coligny OceanViews w/new bikes/chairs

South End

Micah N.

A hotel room with a balcony, a dining area, and a seating area with a view of the ocean.

11. Marriott's Monarch at Sea Pines

Sea Pines

Cory

$222 nightly

Nov 19 - Nov 20

Total with taxes and fees

A spacious living area with a high ceiling, large windows, and a central seating arrangement.

12. Marriott's Heritage Club

Sea Pines

Christine

$145 nightly

Dec 2 - Dec 3

Total with taxes and fees

A room with a sliding glass door leading to an outdoor patio with a table and chairs, a ceiling fan, and a flat-screen TV mounted on the wall.

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

South End

Beth T.

$240 nightly

Nov 10 - Nov 11

Total with taxes and fees

A view of a beachfront property with palm trees and a clear sky.

14. OceanEscape – Steps to the Beach

South End

Renee A.

$231 nightly

Nov 10 - Nov 11

Total with taxes and fees

A balcony with a table and chairs, overlooking a landscaped garden and distant hills.

15. Oceanfront Hilton Head Island Condo w/ Pool!

South End

Beverly

$273 nightly

Nov 10 - Nov 11

Total with taxes and fees

16. STUNNING ocean view! Brand new listing

South End

xiaoming w.

$224 nightly

Nov 10 - Nov 11

Total with taxes and fees

A balcony with a view of the ocean, palm trees, and a building with large windows.

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

South End

Allison A.

A balcony with a wicker chair and a surfboard, overlooking a beach with palm trees and a clear sky.

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

South End

Matt W.

$230 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern building with a view of the ocean.

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

South End

Griffith S.

$240 nightly

Nov 10 - Nov 11

Total with taxes and fees

A covered outdoor area with a view of the sea, featuring a railing and a pathway.

20. Sunset Dunes Direct Beach Access

South End

Celeste G.

View all properties

Find vacation rentals that suit your style

Top Hilton Head Island Hotel Reviews

A pool area with lounge chairs and umbrellas, surrounded by palm trees.

Hilton Grand Vacations Club Ocean Oak Resort Hilton Head

South End

10/10 Excellent

Gregory

A covered outdoor area with a pool, lounge chairs, and a sofa.

Marriott's SurfWatch

Mid Island

10/10 Excellent

Anonymous traveler

A view through large windows of a landscaped garden with a circular stone feature, surrounded by potted plants.

Montage Palmetto Bluff

Palmetto Bluff

10/10 Excellent

We visited Montage bluffton couple of days ago. We cannot describe how delighted we were from the moment we reached the hotel till we left. We were greeted at the gate and were given a cd to tell us more about bluffton history on our way to the hotel grounds. Once we reached the hotel a wonderful team greeted us. The receptionist gave my 2 year old stuffed animals that she loved. The room was nice with a spacious bathroom, consideration to little details was obvious, like umbrellas, bath...

al qudah family

A modern kitchen with a built-in island, a flat-screen TV, and a coffee station.

Best Western Sea Island Inn

Historic District

10/10 Excellent

Brooke

A waterfront hotel with multiple red-roofed buildings, a dock, and a marina.

Disney's Hilton Head Island Resort

Mid Island

10/10 Excellent

Marriott's Heritage Club

Sea Pines

10/10 Excellent

Anonymous traveler

An aerial view of a resort with multiple buildings, a central swimming pool, and a beach in the background.

Marriott's Grande Ocean

South End

10/10 Excellent

It is so nice to have a full kitchen and grills right outside, especially when you have a child with several food allergies (gluten, soy, milk and corn). And there's also a whole food close by which is great for us. The hotel staff is very friendly and accommodating. My parents were home with my 5 year old son when he locked then out of the master bedroom and the second bathroom. I called the front desk and they sent Nate (maintenance engineer) right over who opened the doors for them. He was...

Cristina

An indoor swimming pool with clear glass ceilings, multiple lounge chairs, and a view of the outdoors.

Marriott's Barony Beach Club

Mid Island

10/10 Excellent

lisa

Marriott's Harbour Point and Sunset Pointe at Shelter Cove

Mid Island

10/10 Excellent

Me and my family live about 2 1/2 hours away from HHI, so we come to this beautiful island several times a year. We've stayed at many different hotels during our past visits. I MUST say that this hotel was by far the nicest we've every stayed in. The cleanliness was just unbelievable. The Location was prefect. Our room faced the river and marsh, the seen was amazing. My wife didn't won't to leave. I would recommend this hotel to everyone no matter your age or family size.

Robert

A Holiday Inn Express hotel with a covered entrance, columns, and a well-lit facade.

Holiday Inn Express Bluffton at Hilton Head Area by IHG

Bluffton

10/10 Excellent

Bill

Marriott's Monarch at Sea Pines

Sea Pines

10/10 Excellent

Phil

A hotel room with a bed, a desk, a chair, a small table, a TV mounted on the wall, and a window with curtains.

Palmera Inn and Suites

South End

10/10 Excellent

Shaneke

A Courtyard by Marriott hotel with a brick facade, multiple balconies, and a covered entrance area.

Courtyard by Marriott Hilton Head Island

South End

10/10 Excellent

Location, Location, Location! Walk to the beach. Walk to restaurants. Walk to shop and groceries. HOWEVER: I originally chose you for your pictures of your pool. Your page states nothing about it being closed for the season. We're near the Canadian border and motels have OUTDOOR HEATED POOLS IN THE WINTER! You have no excuse. GOOGLE: Polar Plunge. People cut holes in the ice of Lake Superior and dive in!

David

A resort with multiple swimming pools, sun loungers, and a view of the ocean.

Omni Hilton Head Oceanfront Resort

Mid Island

10/10 Excellent

Milan

A covered outdoor patio with seating, a fire pit, and a brick wall.

Home2 Suites by Hilton Hilton Head

Mid Island

10/10 Excellent

Anonymous traveler

Marriott's Harbour Club

Sea Pines

10/10 Excellent

Nicole

An outdoor seating area with a brick fire pit, a sofa, and a table.

SpringHill Suites by Marriott Hilton Head Island

Mid Island

10/10 Excellent

Jason

Find out more about Hilton Head Island

Everything you need to know about Hilton Head Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hilton Head Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hilton Head Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Hilton Head Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $95 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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 vacation rentals in Hilton Head Island?

Yes, you can find vacation rentals in Hilton Head Island close to The Sandbox, or you can select a 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 vacation rentals that Hilton Head Island has to offer?

New Four BR Luxury Vacation Home on Hilton Head: Visitors give good reviews to this Hilton Head Island vacation home rental, which 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 you can cook with friends or family. Other favorite 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 vacation rentals are there in Hilton Head Island?

With 986 Expedia vacation rentals, you're sure 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 vacation rental in Hilton Head Island like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Hilton Head Island. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for small groups.

Hilton Head Island Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Hilton Head Island vacation rentals

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

2. Marriott's Harbour Club

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

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

5. Beach Daze-Gorgeous new shower! Bikes Included

6. Castaways King Villa on Beach, Free Bikes!

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

8. Beachy Keen Seaside Villa Near Coligny W/Bikes!

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

10. Totally Beachin' Coligny OceanViews w/new bikes/chairs

11. Marriott's Monarch at Sea Pines

12. Marriott's Heritage Club

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

14. OceanEscape – Steps to the Beach

15. Oceanfront Hilton Head Island Condo w/ Pool!

16. STUNNING ocean view! Brand new listing

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

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

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

20. Sunset Dunes Direct Beach Access

Find vacation rentals that suit your style

Top Hilton Head Island Hotel Reviews

Hilton Grand Vacations Club Ocean Oak Resort Hilton Head

10/10 Excellent

Find out more about Hilton Head Island

Everything you need to know about Hilton Head Island vacation rentals

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

How to find incredible deals on Hilton Head Island rentals

Frequently Asked Questions

Are there vacation rentals in Hilton Head Island?

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

How many vacation rentals are there in Hilton Head Island?

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

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

Explore a world of travel with Expedia