Vacation Rentals & Beach Rentals in Hilton Head

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Hilton Head Island - Spa on Port Royal Sound

Hilton Head apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Quiet relaxation” We absolutely loved our stay! The condo is on the third floor, so there’s great views of the grounds, and a walking path to the ocean and pier. The Plantation was extremely quiet, and the people we did come across were welcoming and friendly. The condo was clean, cozy, stocked with necessary kitchen and even toiletries for the bathroom! That was a pleasant surprise. We spent most of our time sitting on the screened porch listening to the fountains and birds. The owner is very responsive to texts and emails. We definitely recommend this as a vacation spot, and will be back.

Match: Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$115

Spacious Pet Friendly Sea Pines Home, Free Bikes, Private Pool, Walk to Beach

Hilton Head house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$1,669

Sea Pines Home, Private Pool, Golf Views, Walk to Beach, Free Bikes

Hilton Head house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$1,575

4th Row Ocean, 4 Bd, Dog Friendly, Heated Private Pool, Free Bikes

Hilton Head house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$833

Gated community condo 200/300 steps to beach

Hilton Head apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great location and clean unit” The location of this unit is great. The back gate is just outside the unit and the walk to the beach is an easy one. The walk or bike ride to Coligny Beach Park and the shopping plaza was very easy. It's about half a mile. The beach off Ibis St is quiet and not nearly as crowded as the beach at the Shipyard Plantation club house. The club house beach was great because of the restroom facilities and ability to rent chairs and an umbrella, but our family preferred the quieter beach access outside the back gate. Also, the pictures do not do this unit justice. It was much nicer than I expected. The unit was clean and quiet. Our week long stay was great.

Match: Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$345

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6 Bedroom Direct Oceanfront Luxury in South Forest Beach

Hilton Head house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 18

1 of 2 match: Private outdoor pool (unheated), Private outdoor pool (heated)

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Price per night from

$2,530

North Shore Place Unit 405

Hilton Head condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Private outdoor pool (heated)

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Price per night from

$518

Desirable Seacrest Oceanfront

Hilton Head condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Private outdoor pool (heated)

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Price per night from

$518

Newly Updated Breakers Villa. Sleeps 4, Beachfront, Pool

Hilton Head villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Private outdoor pool (heated)

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Price per night from

$334

331 Breakers, Fully Remodeled! Beautiful Oceanfront, Pool, Beach Free Bikes

Hilton Head villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Private outdoor pool (heated)

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Price per night from

$334

Direct Oceanfront Views, 339 Breakers. Sleeps 4

Hilton Head villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Private outdoor pool (heated)

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Price per night from

$367

29 Sandpiper

Hilton Head house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 20

1 of 2 match: Private outdoor pool (unheated), Private outdoor pool (heated)

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Price per night from

$1,149

Beachfront Paradise, 336 Breakers. Sleeps 4-6, Free Bikes

Hilton Head villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Private outdoor pool (heated)

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Price per night from

$367

Shorewood 103 - Oceanfront 1st Floor Condo

Hilton Head apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Conditions of Condo” We had a great time while on the island. The location of Shorewood with beach and pool was great for our 6 year old son. The number of families with kids made the trip enjoyable. The condo we stayed 103 is in need of some repair however. The bathrooms were a bit "worn" and in need of some cosmetic upgrading. We are planning to stay at Shorewood again August 2014.

1 of 2 match: Private outdoor pool (unheated), Private outdoor pool (heated)

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Price per night from

$440

Shorewood 202 - Direct Oceanfront Beautiful Condo!!

Hilton Head apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Perfect Location!” We stayed four nights at this great condo and it just wasn't long enough! Shorewood is the perfect location and unit 202 was a great location with in the complex. The second floor view was beautiful while not having to use the elevator or climb a lot of stairs. We were very happy with the condo itself. The kitchen is beautifully updated and well stocked. While the rest of the unit could use a little bit of updating and freshening up, it was clean and it wouldn't stop me from renting here again. My only complaint was that we didn't have more time!

1 of 2 match: Private outdoor pool (unheated), Private outdoor pool (heated)

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Price per night from

$415

Beautifully Decorated, Cozy, Warm And Inviting 1st Floor Retreat!

Hilton Head condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$98

Responds fast! avg. 3 hours 47 minutes

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$208

Responds fast! avg. 3 hours 47 minutes

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$139

Comfortable Beach Home with Private Heatable Pool & Hot Tub! Easy Peasy 8 Min.

Hilton Head house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 47 minutes

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$379

Responds fast! avg. 3 hours 47 minutes

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$312

Responds fast! avg. 3 hours 47 minutes

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$116

Responds fast! avg. 3 hours 47 minutes

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$115

Responds fast! avg. 3 hours 47 minutes

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$139

Responds fast! avg. 3 hours 47 minutes

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$156

Responds fast! avg. 3 hours 47 minutes

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$417

Sea Pines home with private pool. Light filled and open floor plan.

Hilton Head house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Private outdoor pool (heated)

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Price per night from

$357

Oceanfront, Sea Pines, 22 Black Skimmer Ln.

Hilton Head house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Responds fast! avg. 9 minutes

1 of 2 match: Private outdoor pool (unheated), Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,637

REMODELED 2 BR 2 BATH UNIT IN ADMIRALS

Hilton Head condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$213

Charming Sea Pines Home, Private Pool, Free Bikes

Hilton Head house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,510

21 Heron - Oceanfront Home, Private Boardwalk, Remodeled Back Deck 2023

Hilton Head house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$575

1 St. George Rd.

Hilton Head house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$245

1 Osprey - Beach Cottage with HUGE pool! Steps to the sand

Hilton Head house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Great week at the beach!” This is our second year staying at 1 Osprey and we really like the house and location. It is clean, nicely decorated, and equipped with everything you need on vacation.

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$260

65 Baynard Cove Rd - Lagoon Views in Sea Pines

Hilton Head house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$335

Short Walk to the Beach, Private Pool/Spa, Near Coligny Plaza

Hilton Head house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

“Since we found this house we've not stayed anywhere else!” This was our 3rd year staying at 2 Bayberry and we have already booked it for next year! It is perfect for the whole family with a 2nd den upstairs. It is also wonderful working with the ladies at Beachside Getaway! Whatever we need we just call them up. When I arrived this year I noticed the tea kettle was missing so I asked them about it...one was delivered the next day! We wouldn't stay anywhere else!!!

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$225

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$290

14 Bittern St - 5 Bedroom Home close to Ocean and Coligny

Hilton Head house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

“Fabulous location, great vacation for the whole family!” Our family has been coming to Hilton Head on vacation for over 20 years. With our children marrying and blessing us with grandchildren, we needed a larger place to stay to include everyone comfortably. 14 Bittern is in a fabulous location, steps from the beach and Coligny plaza. There are plenty of bedrooms, a large gathering area, and wonderful outdoor space for everyone to spread out. The house is not "fancy" and the rental price reflects that, but it is perfectly nice and comfortable with a lot of people and especially children it's nice not to have to worry about messing something up. The fabulous location makes this a steal! Plenty of parking for everyone too. The rental agency, Beachside Getaway, was very accommodating and followed up several times to be sure all was to our satisfaction. We had a great time!

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

13 Sandpiper Street - Pet Friendly

Hilton Head house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“One of our best trips EVER at HHI” Very close to beach and within short bike ride to Coligny. Pet friendly and VERY clean which is a must for me! Lots of space

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$305

4 Pelican Street - 4 Bedroom Dog Friendly North Forest Beach Home

Hilton Head house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$320

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