50 Best Hilton Head Vacation rentals on Holiday Lettings - Beach rentals

Close

Hilton Head

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

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

1,339 Vacation rentals

Travelers going to Hilton Head are booking May dates now. Secure your vacation rental today and have the perfect trip.

10

Hilton Head Vacation condo rental

Coastal South Carolina / Hilton Head

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
HILTON HEAD ISLAND, SOUTH CAROLINA, USA. "SMILING FACES, BEAUTIFUL PLACES"PRETTY 2 BED/2 BATHROOM CONDO IN FIDDLERS COVE, 3 MINUTES WALK FROM AWARD WINNING BEACH. GOLFERS PARADISE. CYCLE THE ISLAND, GO TO THE GYM, PLAY TENNIS IN 10 TENNIS COURTS ON SI  …see more

from $135 / night

$875 / week

Book View

from $135 / night

32

Villa rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The Island: Hilton Head Island may only be 12 miles by 5 miles wide, but you’ll find everything you need here for the ultimate Island retreat. Enjoy days basking in the sun on some of the best beaches in the country. Get into the swing of things at your choice of  …see more

from $90 / night

$525 - $1030 / week

Book View

from $90 / night

(1) Excellent 

14

Hilton Head Vacation villa rental

Coastal South Carolina / Hilton Head

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
Our villa is an end unit with lots of natural light and magnificent views over the waterway and the George Fazio golf course. The deck, which overlooks the 3rd and 7th fairways, provides mile long water vistas while the dining room has a great view of the 7th green and  …see more

from $116 / night

$810 - $1150 / week

Book View

from $116 / night

10

Vacation villa in Hilton Head

Coastal South Carolina / Hilton Head

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Immaculately clean unit. Tile and carpet throughout. The views are outstanding from the unit's balcony. This Villa is a beautifully decorated one bedroom stay with a queen bed, queen-size sleeper sofa, and built-in bunk beds for 2 children (sleeps 4-6 comfortabl  …see more

from $100 / night

$600 - $750 / week

Book View

from $100 / night

(10) Excellent 

66

Coastal South Carolina / Hilton Head

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

 …see more

from $91 / night

$636 - $1360 / week

Book View

from $91 / night

(4) Excellent 

26

Coastal South Carolina / Hilton Head

3 8 Min stay varies

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

 …see more

from $160 / night

$960 - $1960 / week

Book View

from $160 / night

18

Coastal South Carolina / Hilton Head

2 10 Min stay varies

  • 2 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $169 / night

$825 - $1775 / week

Inquire View

from $169 / night

26

Coastal South Carolina / Hilton Head

Studio 12 7 nights min

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

 …see more

from $422 / night

$2950 - $7850 / week

Inquire View

from $422 / night

(11) Very Good 

21

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $75 / night

$525 - $850 / week

Book View

from $75 / night

30

Coastal South Carolina / Hilton Head

Studio 16 7 nights min

  • Studio
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $600 / night

$3500 - $9900 / week

Inquire View

from $600 / night

(4) Very Good 

24

Coastal South Carolina / Hilton Head

2 6 Min stay varies

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

 …see more

from $249 / night

$1245 - $2695 / week

Inquire View

from $249 / night

(4) Very Good 

30

Coastal South Carolina / Hilton Head

Studio 10 7 nights min

  • Studio
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $143 / night

$995 - $2895 / week

Inquire View

from $143 / night

(21) Excellent 

22

Coastal South Carolina / Hilton Head

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $125 / night

$750 - $950 / week

Book View

from $125 / night

(2) Good 

26

Coastal South Carolina / Hilton Head

2 6 Min stay varies

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

 …see more

from $129 / night

$665 - $1435 / week

Inquire View

from $129 / night

(10) Very Good 

20

Coastal South Carolina / Hilton Head

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $209 / night

$1045 - $2255 / week

Inquire View

from $209 / night

(15) Very Good 

28

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $94 / night

$548 - $737 / week

Book View

from $94 / night

29

Coastal South Carolina / Hilton Head

Studio 16 7 nights min

  • Studio
  • Sleeps 16
  • 7 nights min
  • Ask about children
  • Air conditioning

 …see more

from $165 / night

$1150 - $2250 / week

Inquire View

from $165 / night

(3) Very Good 

25

Coastal South Carolina / Hilton Head

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $209 / night

$1045 - $2255 / week

Inquire View

from $209 / night

(28) Excellent 

27

Coastal South Carolina / Hilton Head

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $70 / night

$475 - $850 / week

Book View

from $70 / night

(3) Excellent 

25

Coastal South Carolina / Hilton Head

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool

 …see more

from $310 / night

$1790 - $2295 / week

Book View

from $310 / night

25

Coastal South Carolina / Hilton Head

Studio 7 7 nights min

  • Studio
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $128 / night

$895 - $2195 / week

Inquire View

from $128 / night

(6) Excellent 

27

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $140 / night

$900 - $1145 / week

Book View

from $140 / night

22

Coastal South Carolina / Hilton Head

Studio 6 7 nights min

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

 …see more

from $114 / night

$795 - $1495 / week

Inquire View

from $114 / night

24

Coastal South Carolina / Hilton Head

Studio 8 7 nights min

  • Studio
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $114 / night

$795 - $1995 / week

Inquire View

from $114 / night

27

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.2 mi
  • Swimming pool
  • Child friendly

 …see more

from $90 / night

$600 - $850 / week

Book View

from $90 / night

24

Coastal South Carolina / Hilton Head

Studio 14 7 nights min

  • Studio
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $428 / night

$2995 - $6995 / week

Inquire View

from $428 / night

(3) Very Good 

24

Coastal South Carolina / Hilton Head

Studio 20 7 nights min

  • Studio
  • Sleeps 20
  • 7 nights min
  • Ask about children
  • Ask about pets

 …see more

from $850 / night

$3221 - $11954 / week

Inquire View

from $850 / night

(8) Good 

21

Coastal South Carolina / Hilton Head

Studio 4 7 nights min

  • Studio
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $71 / night

$495 - $1095 / week

Inquire View

from $71 / night

(2) Very Good 

24

Coastal South Carolina / Hilton Head

4 10 Min stay varies

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

 …see more

from $209 / night

$1055 - $2275 / week

Inquire View

from $209 / night

29

Coastal South Carolina / Hilton Head

Studio 14 7 nights min

  • Studio
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $550 / night

$3775 - $9975 / week

Inquire View

from $550 / night

(8) Very Good 

35

Coastal South Carolina / Hilton Head

2 6 3 nights min

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

 …see more

from $79 / night

$500 - $675 / week

Book View

from $79 / night

(4) Very Good 

17

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $94 / night

$564 - $1400 / week

Book View

from $94 / night

(1) Very Good 

29

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $90 / night

$500 - $903 / week

Book View

from $90 / night

(8) Very Good 

25

Coastal South Carolina / Hilton Head

Studio 8 7 nights min

  • Studio
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $85 / night

$595 - $1595 / week

Inquire View

from $85 / night

24

Coastal South Carolina / Hilton Head

Studio 12 7 nights min

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

 …see more

from $465 / night

$3250 - $5550 / week

Inquire View

from $465 / night

31

Coastal South Carolina / Hilton Head

Studio 14 7 nights min

  • Studio
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $514 / night

$3595 - $9695 / week

Inquire View

from $514 / night

(5) Very Good 

19

Coastal South Carolina / Hilton Head

2 8 Min stay varies

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

 …see more

from $119 / night

$585 - $1265 / week

Inquire View

from $119 / night

(5) Excellent 

25

Coastal South Carolina / Hilton Head

2 6 Min stay varies

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

 …see more

from $119 / night

$595 - $1285 / week

Inquire View

from $119 / night

20

Coastal South Carolina / Hilton Head

Studio 4 7 nights min

  • Studio
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $157 / night

$1095 - $2195 / week

Inquire View

from $157 / night

(2) Very Good 

22

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $75 / night

$800 / week

Book View

from $75 / night

1