COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Search 105,200+ Vacation Rentals

Hilton Head Vacation Rentals & Beach Rentals with Swimming Pool - 105 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

105 Vacation rentals

Filters applied: Swimming pool

(4)

1 / 97

Hilton Head House

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

Responds fast! Avg. 3 hours 38 minutes

$802.00

Excellent (4 reviews)

Book

from $802.00 / night

(6)

1 / 21

Hilton Head Villa

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

Responds fast! Avg. 3 hours 15 minutes

$297.00

Average (6 reviews)

Book

from $297.00 / night

(21)

1 / 23

Hilton Head Apartment

  • 2
  • 6
  • 7 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

$344.00

Very Good (21 reviews)

Book

from $344.00 / night

(4)

1 / 31

Hilton Head Villa

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

Responds fast! Avg. 3 hours 15 minutes

$125.00

Very Good (4 reviews)

Book

from $125.00 / night

(1)

1 / 27

Hilton Head Villa

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

Responds fast! Avg. 3 hours 15 minutes

$274.00

Average (1 reviews)

Book

from $274.00 / night

(18)

1 / 43

Hilton Head Condo

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

$132.00

Excellent (18 reviews)

Book

from $132.00 / night

(14)

1 / 25

Hilton Head Villa

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

Responds fast! Avg. 3 hours 15 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 (14 reviews)

Book

from $228.00 / night

(13)

1 / 12

Hilton Head Condo

  • 2
  • 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 18 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 (13 reviews)

Book

from $172.00 / night

(2)

1 / 18

Hilton Head House

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

$155.00

Excellent (2 reviews)

Inquire

from $155.00 / night

1 / 18

Hilton Head Villa

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

$150.00

Inquire

from $150.00 / night

1 / 30

Hilton Head House

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

$165.00

Inquire

from $165.00 / night

1 / 26

Hilton Head Villa

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

$190.00

Inquire

from $190.00 / night

1 / 35

Hilton Head House

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

$575.00

Inquire

from $575.00 / night

1 / 32

Hilton Head Villa

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

$135.00

Inquire

from $135.00 / night

(24)

1 / 52

Hilton Head House

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

$650.00

Excellent (24 reviews)

Inquire

from $650.00 / night

(23)

1 / 30

Hilton Head House

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

$250.00

Very Good (23 reviews)

Inquire

from $250.00 / night

1 / 21

Hilton Head House

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

$155.00

Inquire

from $155.00 / night

(19)

1 / 29

Hilton Head House

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

$330.00

Very Good (19 reviews)

Inquire

from $330.00 / night

(5)

1 / 23

Hilton Head House

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

$285.00

Very Good (5 reviews)

Inquire

from $285.00 / night

(7)

1 / 27

Hilton Head Villa

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

$145.00

Very Good (7 reviews)

Inquire

from $145.00 / night

1 / 20

Hilton Head House

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

$170.00

Inquire

from $170.00 / night

(16)

1 / 27

Hilton Head House

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

$100.00

Excellent (16 reviews)

Inquire

from $100.00 / night

(3)

1 / 27

Hilton Head House

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

$250.00

Very Good (3 reviews)

Inquire

from $250.00 / night

(1)

1 / 31

Hilton Head Villa

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

$175.00

Excellent (1 reviews)

Inquire

from $175.00 / night

1 / 24

Hilton Head Villa

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

$180.00

Inquire

from $180.00 / night

1 / 27

Hilton Head Cottage

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

$205.00

Inquire

from $205.00 / night

1 / 28

Hilton Head House

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

$300.00

Inquire

from $300.00 / night

(20)

1 / 33

Hilton Head House

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

$250.00

Very Good (20 reviews)

Inquire

from $250.00 / night

1 / 28

Hilton Head Villa

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

$165.00

Inquire

from $165.00 / night

(13)

1 / 48

Hilton Head House

  • 7
  • 19
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$950.00

Excellent (13 reviews)

Inquire

from $950.00 / night

1 / 25

Hilton Head Villa

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

$150.00

Inquire

from $150.00 / night

(6)

1 / 85

Hilton Head House

  • 7
  • 22
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$2,870.00

Excellent (6 reviews)

Inquire

from $2,870.00 / night

(19)

1 / 27

Hilton Head House

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

$420.00

Very Good (19 reviews)

Inquire

from $420.00 / night

(4)

1 / 28

Hilton Head Villa

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

$150.00

Excellent (4 reviews)

Inquire

from $150.00 / night

(6)

1 / 67

Hilton Head House

  • 7
  • 20
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$695.00

Very Good (6 reviews)

Inquire

from $695.00 / night

(2)

1 / 26

Hilton Head Villa

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

$155.00

Excellent (2 reviews)

Inquire

from $155.00 / night

(4)

1 / 33

Hilton Head House

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

$250.00

Very Good (4 reviews)

Inquire

from $250.00 / night

(21)

1 / 49

Hilton Head House

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

$400.00

Very Good (21 reviews)

Inquire

from $400.00 / night

(4)

1 / 25

Hilton Head Villa

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

$165.00

Very Good (4 reviews)

Inquire

from $165.00 / night

1 / 27

Hilton Head Apartment

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

$375.00

Inquire

from $375.00 / night