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Hilton Head Vacation Rentals & Beach Rentals with Swimming Pool - 438 Rentals Available.

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438 Vacation rentals

Filters applied: Swimming pool

1 / 21

Hilton Head Villa

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

Responds fast! Avg. 3 hours 51 minutes

$89.00

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from $89.00 / night

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(31)

1 / 26

Hilton Head Villa

  • 1
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 23 minutes

“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 (31 reviews)

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from $75.00 / 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

$120.00

Very Good (21 reviews)

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from $120.00 / night

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(2)

1 / 26

Hilton Head House

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

Responds fast! Avg. 2 hours 57 minutes

$700.00

Excellent (2 reviews)

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from $700.00 / night

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(1)

1 / 31

Hilton Head House

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

Responds fast! Avg. 2 hours 57 minutes

$650.00

Excellent (1 reviews)

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from $650.00 / night

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(18)

Certificate of Excellence

1 / 25

Hilton Head Apartment

  • 1
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Responds fast! Avg. 46 minutes

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 (18 reviews)

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from $109.00 / night

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(2)

1 / 31

Hilton Head Villa

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

Responds fast! Avg. 3 hours 51 minutes

$89.00

Excellent (2 reviews)

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from $89.00 / night

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(1)

1 / 18

Hilton Head Villa

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

Responds fast! Avg. 3 hours 51 minutes

$174.00

Average (1 reviews)

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from $174.00 / night

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(3)

1 / 40

Hilton Head Condo

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

$80.00

Very Good (3 reviews)

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from $80.00 / night

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(18)

1 / 39

Hilton Head Condo

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

$80.00

Excellent (18 reviews)

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from $80.00 / 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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(10)

1 / 25

Hilton Head Villa

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

Responds fast! Avg. 3 hours 51 minutes

“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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(1)

1 / 18

Hilton Head Villa

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

Responds fast! Avg. 2 hours 36 minutes

$170.00

Excellent (1 reviews)

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from $170.00 / night

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1 / 22

Hilton Head House

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

Responds fast! Avg. 2 hours 57 minutes

$600.00

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from $600.00 / night

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(2)

1 / 24

Hilton Head House

  • 7
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 36 minutes

“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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(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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(9)

1 / 12

Hilton Head Condo

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

Responds fast! Avg. 2 hours 7 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

$150.00

Excellent (9 reviews)

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from $150.00 / night

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1 / 15

Hilton Head House

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

$251.00

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from $251.00 / night

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(4)

1 / 47

Hilton Head House

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

$2,001.00

Excellent (4 reviews)

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from $2,001.00 / night

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(1)

1 / 43

Hilton Head House

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

Responds fast! Avg. 36 minutes

$600.00

Excellent (1 reviews)

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from $600.00 / night

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1 / 45

Hilton Head House

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

Responds fast! Avg. 36 minutes

$650.00

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from $650.00 / night

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1 / 25

Hilton Head House

  • 5
  • 15
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 26 minutes

$501.00

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from $501.00 / night

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(1)

1 / 29

Hilton Head Villa

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

Responds fast! Avg. 3 hours 51 minutes

$130.00

Average (1 reviews)

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from $130.00 / night

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(9)

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 (9 reviews)

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from $50.00 / night

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(3)

1 / 23

Hilton Head Villa

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

$200.00

Excellent (3 reviews)

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from $200.00 / night

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1 / 25

Hilton Head Villa

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

$340.00

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from $340.00 / night

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(10)

1 / 15

Hilton Head Villa

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

$200.00

Very Good (10 reviews)

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from $200.00 / night

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1 / 36

Hilton Head Villa

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$215.00

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from $215.00 / night

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1 / 23

Hilton Head House

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

$240.00

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from $240.00 / night

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1 / 23

Hilton Head Villa

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

$160.00

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from $160.00 / night

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(5)

1 / 27

Hilton Head Villa

  • 3
  • 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$138.00

Very Good (5 reviews)

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from $138.00 / night

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1 / 27

Hilton Head Villa

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

$180.00

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from $180.00 / night

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1 / 30

Hilton Head Villa

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

$180.00

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from $180.00 / night

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(6)

1 / 27

Hilton Head Villa

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

$300.00

Very Good (6 reviews)

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from $300.00 / night

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1 / 33

Hilton Head Villa

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

$200.00

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from $200.00 / night

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1 / 38

Hilton Head House

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

$200.00

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from $200.00 / night

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(1)

1 / 24

Hilton Head House

  • 5
  • 14
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$560.00

Excellent (1 reviews)

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from $560.00 / night

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(13)

1 / 32

Hilton Head Villa

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

$380.00

Very Good (13 reviews)

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from $380.00 / night

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(10)

1 / 26

Hilton Head Villa

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

$340.00

Very Good (10 reviews)

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from $340.00 / night

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1 / 31

Hilton Head House

  • 5
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$400.00

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from $400.00 / night

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