Southampton vacation rentals

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Booking Insights
Recommended by KAYAK

Best Southampton vacation rentals

Beautiful renovated house with views . Available for the 2026 US OPEN - Southampton - Living room
Beautiful renovated house with views . Available for the 2026 US OPEN
Southampton, NY
10Wonderful(14)
House
$828+
Check availability
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets! - Southampton - Living room
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton, NY
8.8Very good(9)
House
Free Wi-Fi
$1,414+
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1898 Renovated Cottage 100' from Bullhead Bay - Southampton - Living room
1898 Renovated Cottage 100' from Bullhead Bay
Southampton, NY
9.0Wonderful(2)
House
Free Wi-Fi
$944+
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New Listing: Recently Renovated, Inviting Terrace Overlooking Pool, Minutes - Southampton - Kitchen
New Listing: Recently Renovated, Inviting Terrace Overlooking Pool, Minutes
Southampton, NY
10Wonderful(3)
House
$1,278+
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Waterfront Southhampton Home - Southampton - Kitchen
Waterfront Southhampton Home
Southampton, NY
8.0Very good(2)
House
Free Wi-Fi
$859+
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Beautiful Southampton Cottage with Saltwater Pool steps from Bay - Southampton - Living room
Beautiful Southampton Cottage with Saltwater Pool steps from Bay
Southampton, NY
Cottage
Free Wi-Fi
$933+
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Southampton Summer Retreat - Southampton - Living room
Southampton Summer Retreat
Southampton, NY
House
Free Wi-Fi
$2,458+
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Private Bayfront Living, Water Views - Southampton - Living room
Private Bayfront Living, Water Views
Southampton, NY
10Wonderful(1)
House
$855+
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Luxurious Gated 4-Bedroom retreat with BayOcean View - Southampton - Building
Luxurious Gated 4-Bedroom retreat with BayOcean View
Southampton, NY
10Wonderful(4)
House
$1,712+
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Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More! - Southampton - Living room
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Southampton, NY
10Wonderful(12)
House
Free Wi-Fi
$1,330+
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Southampton House Perfect for Families and Entertaining - Southampton - Kitchen
Southampton House Perfect for Families and Entertaining
Southampton, NY
10Wonderful(16)
House
$1,630+
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Location and views! Located directly on Shinnecock Bay! - Southampton
Location and views! Located directly on Shinnecock Bay!
Southampton, NY
9.1Wonderful(21)
Cottage
Free Wi-Fi
$403+
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Villa Lalam - Southampton
Villa Lalam
Southampton, NY
Villa
Parking
Free Wi-Fi
Pool
Pet friendly
$1,064+
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Villa Perlman - Southampton
Villa Perlman
Southampton, NY
10Wonderful(1)
Villa
Parking
Free Wi-Fi
Pool
Pet friendly
$3,202+
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Villa Revello - Luxury with pool - Southampton
Villa Revello - Luxury with pool
Southampton, NY
Villa
Parking
Free Wi-Fi
Pool
Pet friendly
$1,270+
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4 Bed 2 Bath - Salt Water Pool Close & Beaches - Southampton
4 Bed 2 Bath - Salt Water Pool Close & Beaches
Southampton, NY
10Wonderful(1)
House
Parking
Free Wi-Fi
Pool
Pet friendly
$862+
Check availability
Booking Insights

KAYAK’s insights for vacation rentals in Southampton

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Southampton with confidence.

What is the cheapest day of the week to book a vacation rental in Southampton?

Tuesday offers the lowest rates in Southampton, with an average nightly price of $639. The highest prices are found on Sunday, with average rates at $2,216.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

September
May
$1,730
$1,689
Cheapest month to stay with an average 65% drop in price.
Most expensive month to stay with an average 59% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Southampton vacation rental deals

  • Vacation rentals in Southampton are around 85% more expensive than hotels on average. Search here to compare prices for all accommodation types in Southampton.
  • The best vacation rental properties in Southampton are Charming Village home in the heart of Southampton (9.9, 20 reviews), Location and views! Located directly on Shinnecock Bay! (9.1, 21) and Location and views! Located directly on Shinnecock Bay! (9.1, 21), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Southampton, you should consider visiting during the low season. The cheapest vacation homes in Southampton can be found in September and June.
  • The cheapest night for renting a vacation home in Southampton is Tuesday. In contrast, the most expensive is Sunday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Southampton for 16 days.

FAQs when booking a vacation home in Southampton

  • How much is a vacation rental for a week in Southampton?

    The average price for a weekly Southampton vacation rental found by KAYAK users in the last 2 weeks is $16,136.

  • How much is a vacation rental for a month in Southampton?

    The average price for a monthly Southampton vacation rental found by KAYAK users in the last 2 weeks is $69,156.

  • What types of vacation rentals are available in Southampton?

    There are loads of different property types that you can make your vacation home in Southampton. You’ll find apartments, condos, cottages, houses, homestays and villas.

  • Are there any pet-friendly vacation rentals in Southampton?

    There are a number of dog and pet-friendly Southampton vacation rentals, with around 6% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Southampton?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Southampton?

Our map will help you find the perfect place to stay in Southampton by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Southampton