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Hilton Head Vacation Rentals & Beach Rentals with Swimming Pool - 430 Rentals Available.

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430 Vacation rentals

Filters applied: Swimming pool

1 / 23

Hilton Head Villa

  • 2
  • 7
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$208.00

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from $208.00 / night

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(15)

1 / 25

Hilton Head Apartment

  • 1
  • 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
“We loved loved the location of this condo! It was half a mile from Coligny Plaza, a super fun beachy place with restaurants, bars, and shopping. The condo was clean, very nice, and modern. Quick access directly to the beach was so great!...”
- Review left on 10/14/2017

$109.00

Excellent (15 reviews)

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from $109.00 / night

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1 / 18

Hilton Head Villa

  • 2
  • 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

$174.00

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from $174.00 / night

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(1)

1 / 25

Hilton Head House

  • 5
  • 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$700.00

Excellent (1 reviews)

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from $700.00 / night

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1 / 21

Hilton Head Villa

  • 2
  • 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

$89.00

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from $89.00 / night

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1 / 31

Hilton Head Villa

  • 2
  • 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

$89.00

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from $89.00 / night

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1 / 40

Hilton Head Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$99.00

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from $99.00 / night

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(21)

1 / 18

Hilton Head Apartment

  • 2
  • 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
“Great family rental. Tennis courts, pool close by, bike trails and private beach access. Plenty of room in the condo for the family...”
- Review left on 07/17/2016

$70.00

Very Good (21 reviews)

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from $70.00 / night

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(1)

1 / 18

Hilton Head Villa

  • 2
  • 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$169.00

Excellent (1 reviews)

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from $169.00 / night

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(10)

1 / 17

Hilton Head Condo

  • 1
  • 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We're so happy we chose this villa, and loved absolutely EVERYTHING about it! It's tastefully decorated,comfortable,peaceful and hands down the most relaxing and romantic retreat we've taken in years. We enjoyed breathtaking sunsets each evening...”
- Review left on 01/10/2017

$125.00

Excellent (10 reviews)

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from $125.00 / night

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(28)

1 / 26

Hilton Head Villa

  • 1
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The condo is in a very nice resort in Hilton Head Island. Also, within that resort it is prime location. There are lots of condos with quite a walk to the beach/pool. This one was ocean view/pool view and just a short walk to both. It was also...”
- Review left on 06/21/2016

$75.00

Very Good (28 reviews)

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from $75.00 / night

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(10)

1 / 25

Hilton Head Villa

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We stayed 10 days at Marys Villa, it felt like home. The furniture was comfy. The A/C kept us cool and comfortable. I've stayed at a few different villas in the Spa in the past and Marys was the best by far. Everything we needed was right there. I...”
- Review left on 09/21/2015

$174.00

Very Good (10 reviews)

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from $174.00 / night

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(8)

1 / 22

Hilton Head House

  • 7
  • 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Our family of 9 enjoyed a week at this beautiful home as we came together for a family vacation. We have adult children and one grandchild so the rooms were spacious and more than adequate for our needs. The interior is tastefully decorated and the...”
- Review left on 06/17/2016

$575.00

Excellent (8 reviews)

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from $575.00 / night

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(2)

1 / 16

Hilton Head House

  • 3
  • 10
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
“House was awesome, large and comfortable. We had seven guests and could have easily accommodated 3 more. The pool was great, and the community was wonderful. The house is a little over half a mile from the beach which, in this neighborhood, was...”
- Review left on 06/26/2016

$250.00

Excellent (2 reviews)

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from $250.00 / night

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(1)

1 / 24

Hilton Head House

  • 5
  • 22
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$700.00

Excellent (1 reviews)

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from $700.00 / night

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1 / 15

Hilton Head House

  • 4
  • 10
  • Min stay varies
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly

$250.00

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from $250.00 / night

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1 / 34

Hilton Head Villa

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$145.00

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from $145.00 / night

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(9)

1 / 12

Hilton Head Condo

  • 2
  • 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Very pleasant and clean unit, furnished with everything we needed for our 2 night stay. Enjoyed being able to walk to the beach and the Coligny Plaza for shopping and eating. Owner was very easy to reach when needed. Would highly recommend renting...”
- Review left on 11/01/2016

$125.00

Excellent (9 reviews)

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from $125.00 / night

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(3)

1 / 28

Hilton Head House

  • 8
  • 20
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$2,000.00

Excellent (3 reviews)

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from $2,000.00 / night

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(7)

1 / 50

Hilton Head House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Our trip was wonderful! We had 6 adults, 2 young children, and a dog. Toba and Andy make packing super easy because they provided a high chair, pack n play, toys, and beach towels, chairs, etc. The beach is a short walk and the house is located...”
- Review left on 06/09/2016

$50.00

Excellent (7 reviews)

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from $50.00 / night

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(3)

1 / 24

Hilton Head Villa

  • 3
  • 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“What a great place! We were two couples, each with one high school age student. Megan's place was really lovely. The pictures are spot on. It wasn't too big or too small-just right. Lots of space for us all to spread out. We LOVED the deck...”
- Review left on 04/21/2017

$225.00

Excellent (3 reviews)

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from $225.00 / night

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(1)

1 / 29

Hilton Head Villa

  • 2
  • 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

$174.00

Average (1 reviews)

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from $174.00 / night

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(1)

1 / 24

Hilton Head House

  • 4
  • 16
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$911.00

Excellent (1 reviews)

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from $911.00 / night

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(18)

1 / 39

Hilton Head Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$99.00

Excellent (18 reviews)

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from $99.00 / night

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(2)

1 / 24

Hilton Head House

  • 7
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The house is a great layout for a large family vacation. We had 10 adults and a baby and it was perfectly accommodating. The owners were attentive to any concerns or issues we had upon arrival and were prompt with response - for example, we had one...”
- Review left on 06/03/2015

$450.00

Very Good (2 reviews)

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from $450.00 / night

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1 / 22

Hilton Head House

  • 5
  • 15
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$550.00

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from $550.00 / night

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1 / 45

Hilton Head House

  • 6
  • 18
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$550.00

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from $550.00 / night

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(1)

1 / 43

Hilton Head House

  • 5
  • 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$550.00

Excellent (1 reviews)

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from $550.00 / night

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1 / 25

Hilton Head House

  • 5
  • 15
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$450.00

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from $450.00 / night

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(2)

1 / 19

Hilton Head House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$78.00

Excellent (2 reviews)

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from $78.00 / night

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1 / 33

Hilton Head House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$221.00

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from $221.00 / night

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1 / 24

Hilton Head House

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$150.00

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from $150.00 / night

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1 / 24

Hilton Head Villa

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$125.00

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from $125.00 / night

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1 / 18

Hilton Head House

  • 5
  • 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$428.00

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from $428.00 / night

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1 / 28

Hilton Head House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$99.00

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from $99.00 / night

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1 / 25

Hilton Head Villa

  • 3
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$164.00

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from $164.00 / night

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1 / 30

Hilton Head House

  • 4
  • 11
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$327.00

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from $327.00 / night

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(7)

1 / 23

Hilton Head Villa

  • 2
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$154.00

Excellent (7 reviews)

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from $154.00 / night

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1 / 23

Hilton Head Villa

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$123.00

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from $123.00 / night

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1 / 30

Hilton Head Villa

  • 2
  • 7
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$138.00

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from $138.00 / night

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