285 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Southampton Vacation Rentals with air conditioning(285)

285 Results
$1,100 - $2,100
per night
2 night minimum stay
  • 6 BR,
  • 4 BA,
  • Sleeps 16
2 night minimum stay
(5)
$750 - $1,000
per night
2 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
2 - 7 night minimum stay
(16)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(14)
$500 - $2,150
per night
1 - 5 night minimum stay
  • 6 BR,
  • 3 BA,
  • Sleeps 12
1 - 5 night minimum stay
(5)
$2,800 - $6,300
per week
7 - 14 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 14 night minimum stay
(4)
$750 - $1,250
per night
2 - 14 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 14 night minimum stay
(6)
$7,995 - $8,995
per week
7 night minimum stay
  • 7 BR,
  • 5 BA,
  • Sleeps 18
7 night minimum stay
(25)
$1,000 - $2,500
per night
4 - 6 night minimum stay
  • 6 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 12
4 - 6 night minimum stay
2 Reviews
  • 4 BR,
  • 2 BA,
  • Sleeps 10
1 - 14 night minimum stay
(12)
$3,000 - $6,500
per week
14 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 9
14 night minimum stay
1 Review
$3,967 - $9,333
per week
14 - 31 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 11
14 - 31 night minimum stay
(4)
$1,250 - $4,250
per night
2 - 3 night minimum stay
  • 6 BR,
  • 7 BA,
  • 1 HF BA,
  • Sleeps 14
2 - 3 night minimum stay
(8)
$500 - $1,500
per night
7 - 31 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
7 - 31 night minimum stay
1 Review
$1,250 - $4,250
per night
2 night minimum stay
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 14
2 night minimum stay
(5)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
1 - 2 night minimum stay
$9,872 - $10,161
per week
31 - 39 night minimum stay
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 14
31 - 39 night minimum stay
1 Review
$5,000 - $15,000
per week
7 - 14 night minimum stay
  • 7 BR,
  • 7 BA,
  • 1 HF BA,
  • Sleeps 14
7 - 14 night minimum stay
(4)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 night minimum stay
(4)
$714 - $929
per night
6 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
6 night minimum stay
(8)
  • 5 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 12
14 night minimum stay
2 Reviews
  • 4 BR,
  • 4 BA,
  • Sleeps 8
7 night minimum stay
$11,200
per week
5 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
5 - 7 night minimum stay
$8,500 - $10,000
per week
7 - 14 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 - 14 night minimum stay
$550 - $850
per night
2 - 21 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 21 night minimum stay
(6)
  • 7 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 25
2 Reviews
$2,000 - $8,500
per night
2 - 3 night minimum stay
  • 10 BR,
  • 9 BA,
  • 2 HF BA,
  • Sleeps 30
2 - 3 night minimum stay
  • 5 BR,
  • 4 BA,
  • 3 HF BA,
  • Sleeps 10
14 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 20
2 night minimum stay
$7,500
per night
2 night minimum stay
  • 10 BR,
  • 17 BA,
  • 1 HF BA,
  • Sleeps 40
2 night minimum stay
(3)
  • 6 BR,
  • 5 BA,
  • Sleeps 14
2 Reviews
Advertisement
 

Recent Southampton Reviews

Daughter's 30th Birthday Celebration

5 of 5
I wanted to give this beautiful home a 5 star rating. It could not have been more perfect for our gathering spot to celebrate my daughter's 30th Birthday. Her friends were so grateful to escape the city for the weekend to this paradise. The weather was a bit frigid but the house was warm and toasty. The view of the Shinnecock Bay was amazing as we sat in the family room watching TV and the fire in the fireplace. Swans and ducks swimming in the frozen water. We dined at a local restaurant and got to watch the seals swimming in the water. The home is beautifully decorated and the beds so cozy. The kitchen is fully stocked with any appliance necessary to cook your meals. We explored the Duckwalk Winery for their wine tasting which I highly recommend (ask for Michael) and the Art Museum right next door. We drove to Montauk where they filmed The Affair and found the Lobster Roll where Noah met Allison and the horse stables where Allison's husband family owned. The owner of our VRBO home was so attentive to our needs. It is in a great location in Southampton/Hampton Bays. Order in your groceries from Waldbaums and libations from Bottle Hamptons (delivery is free) and you have a stress free vacation. Kick back and enjoy!
  • Submitted: Feb 27, 2015
  • Stayed: Feb 2015

Beautifully decorated, centrally located home

5 of 5
Our family rented this house for 2 summers and we couldn't have been happier. It is walking distance to Southampton Village, the train station and a short bike ride to Village beaches. Brand new construction, high end furnishings, chef's kitchen made this a perfect family get-away. We highly recommend!
  • Submitted: Nov 24, 2014
  • Stayed: Jan 2014

Great experience

5 of 5
We had a great time in Southampton. Robert and his team were fantastic hosts, the property was exactly as expected, and our group had a lot of fun. Would definitely rent again.
  • Submitted: Nov 8, 2014
  • Stayed: Sep 2014