Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Bungalows
Cabins
Condos
Cottages
Estates
Homes
Studios
Townhomes
Villas
Barns
Boats
Castles
Chalets
Farmhouses
Hotels
Lodges
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Hilton Head Vacation Rentals with Air Conditioning(3,376)

3,376 Results
  • 2 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night minimum stay
(20)
$236 - $336
per night
4 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
4 - 7 night minimum stay
(37)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
(93)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
(21)
$107 - $240
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
3 - 7 night minimum stay
(93)
$614 - $1,329
per night
4 - 7 night minimum stay
  • 5 BR,
  • 5 BA,
  • Sleeps 10
4 - 7 night minimum stay
(29)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 7 night minimum stay
(14)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(51)
$2,095 - $4,795
per week
7 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 12
7 night minimum stay
(22)
$750 - $1,450
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
(16)
  • 4 BR,
  • 1 HF BA,
  • Sleeps 12
3 - 7 night minimum stay
(15)
$125 - $146
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night minimum stay
(15)
$95 - $149
per night
4 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
(35)
  • 2 BR,
  • 2 BA,
  • Sleeps 7
4 - 28 night minimum stay
(38)
$650 - $1,141
per night
4 - 7 night minimum stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 24
4 - 7 night minimum stay
(31)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
4 night minimum stay
(32)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(17)
  • 6 BR,
  • 7 BA,
  • Sleeps 20
4 - 7 night minimum stay
(7)
$295 - $495
per night
4 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
4 - 7 night minimum stay
(22)
$485 - $857
per night
3 - 7 night minimum stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 20
3 - 7 night minimum stay
(11)
  • 1 BR,
  • 1 BA,
  • Sleeps 6
7 night minimum stay
(112)
  • 2 BR,
  • 2 BA,
  • Sleeps 7
2 - 7 night minimum stay
(46)
  • 7 BR,
  • 7 BA,
  • 1 HF BA,
  • Sleeps 22
4 - 7 night minimum stay
(14)
$204 - $325
per night
4 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
(16)
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 20
4 - 7 night minimum stay
(30)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(32)
$140 - $245
per night
4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
4 night minimum stay
(11)
$145 - $285
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(18)
  • 4 BR,
  • 4 BA,
  • Sleeps 10
4 - 7 night minimum stay
(15)
$68 - $164
per night
1 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
1 - 7 night minimum stay
(17)
 

Recent Hilton Head Reviews

Wonderful experience -- fantastic villa!

5 of 5
Our family of four had a wonderful few days at Hilton Head -- and we loved staying in this villa. Stan was extremely helpful and prompt in all of his correspondence, and every thoughtful detail was in place. The villa was absolutely perfect for us, and we're already talking about making Hilton Head an annual destination. And when we do, we'll be contacting Stan to stay here again. We loved it and can't wait to return!
  • Submitted: Oct 18, 2014
  • Stayed: Oct 2014

Fabulous home for vacay in Hilton Head

5 of 5
We wanted a large home near the beach that would comfortably accommodate our family and our daughter's bridal party for her wedding at the Beach Club in the Shipyard. Everyone was amazed by this beautiful home and how much room it provided for all of us. The kitchen is fully equipped and the spacious family room/dining area provides plenty of seating area for a large group. The property manager, Fred, was always available for any questions we had about operating the TV remote and hot tub (which we all loved!). The beach is a short walk and is quite private since it fronts a long stretch of private homes. I can't imagine a more perfect place to stay in Hilton Head.
  • Submitted: Oct 11, 2014
  • Stayed: Sep 2014

Excellent location; roomy but homey.

5 of 5
My family had a wonderful time at Black Skimmer. The pool was great and the house had every ammenity one could ask for. The a/c failed while we were there and it was replaced in one day. We had 2 preschoolers with us so we cooked at the house quite often and loved that everything we needed was available. The Fresh Market grocery was a frequent stop! We ate out at Nosh in Bluffton and Marley's. Breakfast at Signe's is a tradition.
  • Submitted: Oct 1, 2014
  • Stayed: Sep 2014