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Hilton Head Vacation Rentals & Beach Rentals with Swimming Pool - 448 Rentals Available.

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448 Vacation rentals

Filters applied: Swimming pool

1 / 18

Hilton Head Villa

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

$69

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from $69 / night

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(12)

1 / 25

Hilton Head Apartment

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

$109

Excellent (12 reviews)

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from $109 / night

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(24)

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

Very Good (24 reviews)

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from $75 / night

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1 / 23

Hilton Head Villa

  • 2
  • 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$208

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from $208 / night

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1 / 24

Hilton Head Villa

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$69

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from $69 / night

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(1)

1 / 24

Hilton Head House

  • 5
  • 21
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$550

Excellent (1 reviews)

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from $550 / night

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1 / 15

Hilton Head House

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

$250

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from $250 / 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

Very Good (21 reviews)

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from $70 / night

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1 / 24

Hilton Head House

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

$650

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from $650 / night

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(1)

1 / 24

Hilton Head House

  • 7
  • 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The house was perfect. One beach block. Heated pool. Sleeps 20. Hot tub. Very clean and well kept. Great family vacation. My daughter graduated from college and we had a family reunion to celebrate. The house was large enough for all to...”
- Review left on 05/18/2016

$400

Excellent (1 reviews)

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from $400 / night

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1 / 22

Hilton Head House

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

$500

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from $500 / night

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1 / 21

Hilton Head Villa

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

$79

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from $79 / night

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1 / 12

Hilton Head House

  • 6
  • 16
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$650

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from $650 / night

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(2)

1 / 24

Hilton Head House

  • 7
  • 14
  • 3 nights min
  • Swimming pool
  • Ask about children
  • 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

$550

Very Good (2 reviews)

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from $550 / 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

Excellent (1 reviews)

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from $169 / night

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(8)

1 / 22

Hilton Head House

  • 7
  • 20
  • Min stay varies
  • Swimming pool
  • Ask about children
  • 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

$499

Excellent (8 reviews)

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from $499 / night

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(1)

1 / 16

Hilton Head House

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

$195

Excellent (1 reviews)

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from $195 / night

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(1)

1 / 43

Hilton Head House

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

$450

Excellent (1 reviews)

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from $450 / night

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(3)

1 / 28

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

$214

Excellent (3 reviews)

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from $214 / night

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1 / 29

Hilton Head Villa

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

$59

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from $59 / night

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1 / 33

Hilton Head Villa

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

$145

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from $145 / night

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(11)

1 / 25

Hilton Head Villa

  • 2
  • 6
  • Min stay varies
  • 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

$59

Very Good (11 reviews)

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from $59 / night

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(2)

1 / 9

Hilton Head House

  • 5
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Our recent stay at Southwind met our expectations and more. The property had everything a large family needed to make our stay pleasurable. My husband is in a wheelchair and found the island on a whole wheelchair friendly. If only one suggestion...”
- Review left on 07/26/2011

$500

Excellent (2 reviews)

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from $500 / night

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(3)

1 / 24

Hilton Head Villa

  • 3
  • 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“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

Excellent (3 reviews)

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from $225 / night

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1 / 31

Hilton Head Villa

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

$79

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from $79 / night

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1 / 28

Hilton Head House

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

$1655

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from $1655 / night

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(9)

1 / 12

Hilton Head Condo

  • 2
  • 5
  • Min stay varies
  • 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

Excellent (9 reviews)

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from $125 / night

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(9)

1 / 36

Hilton Head House

  • 6
  • 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This was the first time we rented a luxury property, and it was for the occasion of our wedding. Being new, we were unfamiliar with the pricing range as well as the general services that might be available. We found Ted to be very reachable and...”
- Review left on 03/06/2017

$550

Excellent (9 reviews)

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from $550 / night

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(1)

1 / 24

Hilton Head House

  • 4
  • 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$769

Excellent (1 reviews)

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from $769 / night

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1 / 22

Hilton Head House

  • 5
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$320

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from $320 / night

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1 / 23

Hilton Head House

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

$560

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from $560 / night

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1 / 21

Hilton Head Villa

  • 2
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$165

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from $165 / night

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1 / 27

Hilton Head House

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$260

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from $260 / night

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1 / 24

Hilton Head House

  • 6
  • 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$600

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from $600 / night

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1 / 24

Hilton Head Villa

  • 3
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$143

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from $143 / night

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1 / 18

Hilton Head Villa

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$140

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from $140 / night

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1 / 23

Hilton Head House

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

$320

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from $320 / night

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1 / 20

Hilton Head Villa

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

$165

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from $165 / night

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1 / 30

Hilton Head House

  • 5
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$422

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from $422 / night

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1 / 27

Hilton Head House

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

$390

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from $390 / night

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