Hilton Head Island Vacation Rentals from $316: Search Short-Term Rentals

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Our top choices for Hilton Head Island vacation rentals

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

1. Marriott's SurfWatch

Mid Island

Crista

$458 nightly

Sep 2 - Sep 3

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

CLAUDIA

$297 nightly

Sep 2 - Sep 3

Total with taxes and fees

A waterfront restaurant with outdoor seating and a view of the water.

3. Disney's Hilton Head Island Resort

Mid Island

Melissa

$282 nightly

Sep 15 - Sep 16

Total with taxes and fees

4. Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

South End

$834 nightly

Sep 4 - Sep 5

Total with taxes and fees

A beach with a row of blue umbrellas and a path leading to the water.

5. Ocean Palms Villas at Port Royal Resort

Mid Island

Melanie

$401 nightly

Sep 10 - Sep 11

Total with taxes and fees

A historic building with a covered porch and a brick pathway.

6. Montage Palmetto Bluff Residences

Palmetto Bluff

john j

$1,584 nightly

Sep 28 - Sep 29

Total with taxes and fees

A modern kitchen with granite countertops, a stainless steel sink, and wooden cabinets.

7. Palmetto Dunes Golf Getaway: Pool + Beach Access!

Mid Island

minoshka

$375 nightly

Sep 6 - Sep 7

Total with taxes and fees

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

8. Marriott's Barony Beach Club

Mid Island

Pauline

$463 nightly

Sep 28 - Sep 29

Total with taxes and fees

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

9. Marriott's Heritage Club

Sea Pines

Christine

$311 nightly

Sep 8 - Sep 9

Total with taxes and fees

10. Steps to Beach-hilton Head Condo-pet Friendly

Mid Island

$475 nightly

Sep 1 - Sep 2

Total with taxes and fees

A wooden boardwalk leading to a gate, surrounded by lush greenery and palm trees.

11. Walk to Bars & Shops: Resort Condo in Hilton Head!

South End

$332 nightly

Sep 13 - Sep 14

Total with taxes and fees

A wooden boardwalk leading to a beach with a bicycle parked on it.

12. Marriott's Monarch at Sea Pines

Sea Pines

Sharon

$411 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

13. Marriott's Grande Ocean

South End

Richard

$507 nightly

Sep 8 - Sep 9

Total with taxes and fees

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

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

Mid Island

$287 nightly

Sep 7 - Sep 8

Total with taxes and fees

A dining area with a glass table, white chairs, a central plant, and a geometric ceiling light fixture.

15. Walk to Beach: Hilton Head Condo w/ Pool Access

Mid Island

LUMINITA

$304 nightly

Sep 7 - Sep 8

Total with taxes and fees

A modern living room with a glass coffee table, a sofa, a white nightstand, and a large mirror.

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

South End

Roger

$353 nightly

Sep 22 - Sep 23

Total with taxes and fees

A dining area with a wooden table, chairs, and a chandelier. There is a painting on the wall and a cabinet with decorative items.

17. Hilton Head Condo: Beach Supplies, Walk to Shore!

Mid Island

"I’m thrilled with the location of this condo. It’s just a quick walk to the beach, and there are also easy-to-access walking, running, and biking trails. There are plenty of local restaurants, food trucks, grocery stores, and attractions nearby. The only downside is that I didn’t receive the email from Evolve with the check-in/out instructions, as it was delivered to my spam folder. The unit was a bit dusty, probably because it was the off-season when I visited, but a quick trip to the local...

Derval

A living room with a flat-screen TV, a fireplace, a sofa, and a dining area with a table and chairs.

18. Serene Hilton Head Island Condo w/ Community Pool!

South End

$395 nightly

Aug 30 - Aug 31

Total with taxes and fees

A spacious living area with a ceiling fan, a dining table with chairs, a sofa, a coffee table, and a TV mounted on the wall.

19. Oceanfront Condo! Breakers 210 w/ Sunrise Views

South End

20. Breakers 328 Oceanfront Hilton Head Condo Direct Beach Access

South End

$654 nightly

Sep 3 - Sep 4

Total with taxes and fees

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Top Hilton Head Island Hotel Reviews

Beach House Resort Hilton Head

10/10 Excellent

"Staff are friendly and the room was clean and comfortable. Would definitely stay again!"

The Westin Hilton Head Island Resort & Spa

10/10 Excellent

"Great experience. Beautiful beach, 3 pools, friendly non-pushy staff, plenty of pool seating, clean rooms, great fitness center, free water daily, decent food, quality covered self parking. The only negative we noticed is that the hallways in our area were loud because there was laminate floors due to beach/pool access. Walls are a little thin. But, no issue with sleeping at all."

Price trends for vacation rentals in Hilton Head Island

Less expensive	More expensive	Next month
January	April	$283

Month	Price
January	$282
February	$303
March	$330
April	$343
May	$314
June	$336
July	$325
August	$304
September	$283
October	$285
November	$293
December	$287

Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Hilton Head Island. Select dates and complete search for nightly totals inclusive of taxes and fees.

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 $316 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.

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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 popular beaches 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?

Spacious Upscale Home with Direct Private Access to the Beach and Heated Pool!: Visitors give good reviews to this Hilton Head Island vacation home rental, which is located on the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade game room. Another good choice for your trip to Hilton Head Island is Custom Built GORGEOUS 5 Bedroom Sea Pines Home w/ Private Pool + Screen Porch.

How many vacation rentals are there in Hilton Head Island?

With 1026 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. Tybee Island Beach and Marine Corps Recruit Depot Parris Island 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

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Check prices for these dates

Our top choices for Hilton Head Island vacation rentals

1. Marriott's SurfWatch

2. Marriott's Harbour Club

3. Disney's Hilton Head Island Resort

4. Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

5. Ocean Palms Villas at Port Royal Resort

6. Montage Palmetto Bluff Residences

7. Palmetto Dunes Golf Getaway: Pool + Beach Access!

8. Marriott's Barony Beach Club

9. Marriott's Heritage Club

10. Steps to Beach-hilton Head Condo-pet Friendly

11. Walk to Bars & Shops: Resort Condo in Hilton Head!

12. Marriott's Monarch at Sea Pines

13. Marriott's Grande Ocean

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

15. Walk to Beach: Hilton Head Condo w/ Pool Access

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

17. Hilton Head Condo: Beach Supplies, Walk to Shore!

18. Serene Hilton Head Island Condo w/ Community Pool!

19. Oceanfront Condo! Breakers 210 w/ Sunrise Views

20. Breakers 328 Oceanfront Hilton Head Condo Direct Beach Access

Find vacation rentals that suit your style

Top Hilton Head Island Hotel Reviews

Beach House Resort Hilton Head

Price trends for vacation rentals in Hilton Head Island

Find out more about Hilton Head Island

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

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