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Hilton Head Vacation Rentals & Beach Rentals with Swimming Pool - 532 Rentals Available.

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532 Vacation rentals

Filters applied: Swimming pool

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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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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(30)

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 (30 reviews)

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from $75.00 / night

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(1)

1 / 24

Hilton Head House

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

$650.00

Excellent (1 reviews)

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from $650.00 / night

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(1)

1 / 31

Hilton Head Villa

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

$89.00

Excellent (1 reviews)

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from $89.00 / night

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(16)

Certificate of Excellence

1 / 25

Hilton Head Apartment

  • 1
  • 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Certificate of Excellence

“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 (16 reviews)

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from $109.00 / 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 / 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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(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 / 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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(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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(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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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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(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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1 / 22

Hilton Head House

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

$600.00

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from $600.00 / 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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(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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(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

$275.00

Excellent (2 reviews)

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from $275.00 / 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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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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(3)

1 / 40

Hilton Head House

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

$2,159.00

Excellent (3 reviews)

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from $2,159.00 / 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)

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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(4)

1 / 33

Hilton Head Villa

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$279.00

Very Good (4 reviews)

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from $279.00 / night

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1 / 22

Hilton Head Villa

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

$280.00

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from $280.00 / night

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1 / 17

Hilton Head Villa

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

$114.00

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from $114.00 / 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 / 29

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)

1 / 28

Hilton Head Villa

  • 3
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$179.00

Average (1 reviews)

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from $179.00 / night

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(2)

1 / 25

Hilton Head Villa

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

$107.00

Average (2 reviews)

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from $107.00 / night

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1 / 24

Hilton Head Villa

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

$78.00

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from $78.00 / 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)

1 / 26

Hilton Head House

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$381.00

Excellent (1 reviews)

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from $381.00 / night

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1 / 23

Hilton Head House

  • 4
  • 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$320.00

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from $320.00 / night

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1 / 22

Hilton Head Villa

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

$152.00

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from $152.00 / night

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(6)

1 / 23

Hilton Head Villa

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

$141.00

Very Good (6 reviews)

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from $141.00 / night

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(5)

1 / 28

Hilton Head Villa

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$399.00

Excellent (5 reviews)

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from $399.00 / night

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1 / 38

Hilton Head House

  • 2
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$99.00

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from $99.00 / night

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