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1,161 Holiday homes

Filters applied: Swimming pool (1,161)

Travellers going to Hilton Head are booking June dates now. Secure your holiday home today and have the perfect trip.

(3) Very Good 

1 / 40

Hilton Head holiday home rental

Coastal South Carolina / Hilton Head

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay

from $185 / night

$1295 - $1995 / week

Book Book View

from $185 / night

(1) Excellent 

1 / 17

Holiday condo with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $91 / night

$675 - $1875 / week

Book Book View

from $91 / night

(4) Excellent 

1 / 24

Holiday home with golf nearby in Hilton Head

Coastal South Carolina / Hilton Head

4 bedroomsSleeps 12Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies

from $501 / night

$2751 - $6000 / week

Book Book View

from $501 / night

(4) Very Good 

1 / 26

Holiday villa with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $121 / night

$750 - $851 / week

Book Book View

from $121 / night

(2) Very Good 

1 / 15

Holiday condo with golf nearby in Hilton Head

Coastal South Carolina / Hilton Head

4 bedroomsSleeps 11Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies

from $315 / night

$1501 - $2351 / week

Book Book View

from $315 / night

(8) Excellent 

1 / 21

Hilton Head holiday villa rental

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $62 / night

$425 - $826 / week

Book Book View

from $62 / night

(30) Excellent 

1 / 41

Holiday villa with swimming pool, tennis court in Hilton Head

Coastal South Carolina / Hilton Head

1 bedroomSleeps 62 nights min stay

  • 1 bedroom
  • Sleeps 6
  • 2 nights min stay

from $110 / night

$675 - $800 / week

Book Book View

from $110 / night

(12) Excellent 

1 / 20

Hilton Head holiday apartment let

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $115 / night

$756 - $945 / week

Book Book View

from $115 / night

(4) Excellent 

1 / 23

Hilton Head holiday apartment let

Coastal South Carolina / Hilton Head

1 bedroomSleeps 43 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay

from $126 / night

$651 - $851 / week

Book Book View

from $126 / night

(10) Very Good 

1 / 28

Holiday villa in Hilton Head

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $89 / night

$524 - $712 / week

Book Book View

from $89 / night

(17) Excellent 

1 / 21

Holiday apartment letting

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $121 / night

$701 - $800 / week

Book Book View

from $121 / night

(2) Excellent 

1 / 23

Holiday apartment with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $141 / night

$750 - $1325 / week

Book Book View

from $141 / night

(6) Excellent 

1 / 10

Apartment rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $200 / night

$1400 / week

Book Book View

from $200 / night

(18) Very Good 

1 / 22

Apartment rental in Hilton Head with shared pool, golf nearby

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 62 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $101 / night

$701 / week

Book Book View

from $101 / night

(8) Excellent 

1 / 22

Hilton Head holiday apartment rental

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $86 / night

$0 / week

Book Book View

from $86 / night

1 / 24

Hilton Head holiday villa rental

Coastal South Carolina / Hilton Head

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $145 / night

$725 - $1365 / week

Book Book View

from $145 / night

(3) Excellent 

1 / 32

Hilton Head holiday villa rental

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 44 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay

from $126 / night

$851 - $895 / week

Book Book View

from $126 / night

(3) Excellent 

1 / 28

Holiday villa in Hilton Head

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $130 / night

$796 - $875 / week

Book Book View

from $130 / night

(7) Very Good 

1 / 60

Holiday apartment in Hilton Head

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $66 / night

$631 - $690 / week

Book Book View

from $66 / night

(9) Excellent 

1 / 11

Holiday apartment with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $75 / night

$526 / week

Book Book View

from $75 / night

1 / 20

Holiday villa with golf nearby in Hilton Head

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 7Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies

from $170 / night

$1200 - $2198 / week

Book Book View

from $170 / night

(1) Excellent 

1 / 13

Holiday condo accommodation

Coastal South Carolina / Hilton Head

1 bedroomSleeps 63 nights min stay

  • 1 bedroom
  • Sleeps 6
  • 3 nights min stay

from $141 / night

$526 / week

Book Book View

from $141 / night

(4) Very Good 

1 / 19

Apartment rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

1 bedroomSleeps 67 nights min stay

  • 1 bedroom
  • Sleeps 6
  • 7 nights min stay

from $93 / night

$651 - $901 / week

Book Book View

from $93 / night

(26) Excellent 

1 / 27

Hilton Head holiday apartment rental

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 8Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies

from $71 / night

$475 - $800 / week

Book Book View

from $71 / night

1 / 26

Holiday villa with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $200 / night

$1051 - $1850 / week

Book Book View

from $200 / night

(2) Excellent 

1 / 13

Holiday apartment with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $275 / night

$1376 / week

Book Book View

from $275 / night

(3) Very Good 

1 / 19

Villa rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $101 / night

$500 - $851 / week

Book Book View

from $101 / night

(4) Excellent 

1 / 24

Hilton Head holiday villa let

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 87 nights min stay

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min stay

from $79 / night

$550 - $1200 / week

Enquire Enquire View

from $79 / night

(3) Very Good 

1 / 16

Holiday condo rental

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $100 / night

$695 - $1420 / week

Book Book View

from $100 / night

(1) Excellent 

1 / 20

Holiday villa with shared pool, golf nearby in Hilton Head

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $93 / night

$651 - $1000 / week

Book Book View

from $93 / night

(9) Very Good 

1 / 22

Holiday villa with shared pool, golf nearby in Hilton Head

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $101 / night

$501 - $875 / week

Book Book View

from $101 / night

1 / 8

Holiday apartment with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay

from $75 / night

$490 - $750 / week

Book Book View

from $75 / night

(5) Excellent 

1 / 27

Holiday villa rental

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $121 / night

$725 - $1070 / week

Book Book View

from $121 / night

(5) Very Good 

1 / 27

Holiday villa in Hilton Head

Coastal South Carolina / Hilton Head

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $121 / night

$701 - $901 / week

Book Book View

from $121 / night

(1) Excellent 

1 / 13

Holiday villa with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $79 / night

$550 - $1051 / week

Enquire Enquire View

from $79 / night

1 / 22

Villa rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay

from $193 / night

$1350 - $1400 / week

Book Book View

from $193 / night

(13) Very Good 

1 / 26

Condo rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 8Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies

from $71 / night

$475 - $800 / week

Book Book View

from $71 / night

(5) Excellent 

1 / 35

Hilton Head holiday apartment rental

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $75 / night

$501 - $675 / week

Book Book View

from $75 / night

1 / 20

Holiday villa in Hilton Head

Coastal South Carolina / Hilton Head

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $150 / night

$901 - $1600 / week

Book Book View

from $150 / night

1 / 18

Hilton Head holiday condo rental

Coastal South Carolina / Hilton Head

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $106 / night

$730 - $1156 / week

Book Book View

from $106 / night

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