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Hilton Head Vacation Rentals & Beach Rentals with Swimming Pool - 102 Rentals Available.

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102 Vacation rentals

Filters applied: Swimming pool

(4)

1 / 97

Hilton Head House

  • 5
  • 14
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$802.00

Excellent (4 reviews)

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from $802.00 / night

(1)

1 / 50

Hilton Head House

  • 6
  • 22
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$687.00

Excellent (1 reviews)

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from $687.00 / night

(1)

1 / 21

Hilton Head Villa

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

Responds fast! Avg. 2 hours 30 minutes

$251.00

Excellent (1 reviews)

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from $251.00 / night

(21)

1 / 23

Hilton Head Apartment

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Responds fast! Avg. 2 hours 47 minutes

“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

$344.00

Very Good (21 reviews)

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from $344.00 / night

(4)

1 / 31

Hilton Head Villa

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

Responds fast! Avg. 2 hours 30 minutes

$251.00

Very Good (4 reviews)

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from $251.00 / night

(3)

1 / 43

Hilton Head Condo

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

Responds fast! Avg. 2 hours 35 minutes

$132.00

Very Good (3 reviews)

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from $132.00 / night

(1)

1 / 18

Hilton Head Villa

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

$294.00

Excellent (1 reviews)

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from $294.00 / night

(2)

1 / 16

Hilton Head House

  • 3
  • 10
  • 7 nights min
  • 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

$344.00

Excellent (2 reviews)

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from $344.00 / night

(11)

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

$500.00

Excellent (11 reviews)

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from $500.00 / night

(1)

1 / 18

Hilton Head Villa

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

Responds fast! Avg. 2 hours 30 minutes

$228.00

Average (1 reviews)

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from $228.00 / night

(18)

1 / 45

Hilton Head Condo

  • 2
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 35 minutes

$121.00

Excellent (18 reviews)

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from $121.00 / night

(9)

1 / 25

Hilton Head Villa

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

Responds fast! Avg. 2 hours 30 minutes

“Accommodations were clean and refreshing. Well within the budget, close to the beach. Looking forward to staying again...”
- Review left on 04/08/2011

$228.00

Very Good (9 reviews)

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from $228.00 / night

(12)

1 / 12

Hilton Head Condo

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

Responds fast! Avg. 2 hours 24 minutes

“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

$172.00

Very Good (12 reviews)

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from $172.00 / night

(1)

1 / 29

Hilton Head Villa

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

Responds fast! Avg. 2 hours 30 minutes

$240.00

Average (1 reviews)

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from $240.00 / night

1 / 42

Hilton Head House

  • 7
  • 16
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$825.00

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from $825.00 / night

(2)

1 / 19

Hilton Head House

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

$165.00

Excellent (2 reviews)

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from $165.00 / night

1 / 18

Hilton Head Villa

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

$165.00

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from $165.00 / night

1 / 33

Hilton Head House

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

$165.00

Inquire

from $165.00 / night

1 / 18

Hilton Head Villa

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

$190.00

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from $190.00 / night

1 / 35

Hilton Head House

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$700.00

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from $700.00 / night

1 / 31

Hilton Head Villa

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

$150.00

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from $150.00 / night

(24)

1 / 48

Hilton Head House

  • 7
  • 16
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$750.00

Excellent (24 reviews)

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from $750.00 / night

(23)

1 / 29

Hilton Head House

  • 4
  • 9
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$445.00

Very Good (23 reviews)

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from $445.00 / night

1 / 22

Hilton Head House

  • 2
  • 7
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$165.00

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from $165.00 / night

(19)

1 / 24

Hilton Head House

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$300.00

Very Good (19 reviews)

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from $300.00 / night

(5)

1 / 26

Hilton Head House

  • 3
  • 9
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$450.00

Very Good (5 reviews)

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from $450.00 / night

(5)

1 / 24

Hilton Head Villa

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

$170.00

Excellent (5 reviews)

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from $170.00 / night

1 / 20

Hilton Head House

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

$175.00

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from $175.00 / night

1 / 45

Hilton Head House

  • 5
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$475.00

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from $475.00 / night

(16)

1 / 24

Hilton Head House

  • 6
  • 19
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$485.00

Excellent (16 reviews)

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from $485.00 / night

1 / 24

Hilton Head Villa

  • 2
  • 7
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$120.00

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from $120.00 / night

(3)

1 / 27

Hilton Head House

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

$450.00

Very Good (3 reviews)

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from $450.00 / night

(1)

1 / 27

Hilton Head Villa

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$200.00

Excellent (1 reviews)

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from $200.00 / night

1 / 24

Hilton Head Villa

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

$195.00

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from $195.00 / night

1 / 25

Hilton Head Cottage

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

$200.00

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from $200.00 / night

(6)

1 / 45

Hilton Head House

  • 7
  • 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$583.00

Very Good (6 reviews)

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from $583.00 / night

1 / 29

Hilton Head House

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

$390.00

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from $390.00 / night

(20)

1 / 26

Hilton Head House

  • 3
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$260.00

Very Good (20 reviews)

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from $260.00 / night

1 / 28

Hilton Head Villa

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

$165.00

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from $165.00 / night

(13)

1 / 42

Hilton Head House

  • 7
  • 18
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$850.00

Excellent (13 reviews)

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from $850.00 / night