Southampton, New York

Vacation Rentals in Southampton, New York

Discover 169 vacation rental properties in Southampton. From 1 to 10 bedrooms. Average $1911/night. 100% have pools.

169 verified listings Book securely on VRBO Prices updated March 2026

169 properties available

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

3 beds 4 baths
PoolA/CWiFiBalcony
$954/night
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3BR 3BA one-level home with Pool.Walk to private bay beach. Tennis, BB, kayak

3BR 3BA one-level home with Pool.Walk to private bay beach. Tennis, BB, kayak

3 beds 3 baths
PoolA/CWiFiBalcony
$706/night
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Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool

Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool

4 beds 3 baths
PoolA/CWiFiBalcony
$1,693/night
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Southampton Private getaway. Private heated salt pool & beach-family fun.

Southampton Private getaway. Private heated salt pool & beach-family fun.

5 beds 3 baths
PoolA/CWiFiBalcony
$699/night
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Southampton Village Charmer - South of Highway

Southampton Village Charmer - South of Highway

4 beds 3 baths
PoolA/CWiFiBalcony
$1,754/night
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Chic Southampton Home, close to Village and Ocean Beaches

Chic Southampton Home, close to Village and Ocean Beaches

3 beds 2 baths
PoolA/CWiFiBalcony
$1,132/night
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Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

3 beds 2 baths
PoolA/CWiFiBalcony
$870/night
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Southampton Beach & Town Cottage

Southampton Beach & Town Cottage

3 beds 1 bath
PoolA/CWiFiBalcony
$918/night
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Luxury - 5 beds, New Pool, Outdoor Kitchen, walk to beach. Luxury throughout.

Luxury - 5 beds, New Pool, Outdoor Kitchen, walk to beach. Luxury throughout.

5 beds 6 baths
PoolA/CWiFiBalcony
$1,030/night
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New Construction Modern Luxury Retreat w 6 Beds

New Construction Modern Luxury Retreat w 6 Beds

6 beds 6 baths
PoolA/CWiFiBalcony
$1,608/night
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Waterfront Beach Cottage with Dock

Waterfront Beach Cottage with Dock

3 beds 4 baths
PoolA/CWiFiBalcony
$1,179/night
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Charming Cottage close to Main Street

Charming Cottage close to Main Street

3 beds 1 bath
PoolA/CWiFiBalcony
$789/night
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New Duplex Apartment

New Duplex Apartment

1 bed 1 bath
PoolA/CWiFiBalcony
$396/night
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South of the highway, walking distance to town.

South of the highway, walking distance to town.

5 beds 6 baths
PoolA/CWiFiBalcony
$2,659/night
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Large 1 bedroom apt on 9 acre estate property

Large 1 bedroom apt on 9 acre estate property

1 bed 1 bath
PoolA/CWiFiBalcony
$203/night
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Southampton Waterfront, Bay Beach & Spectacular Sunsets

Southampton Waterfront, Bay Beach & Spectacular Sunsets

3 beds 3 baths
PoolA/CWiFiBalcony
$502/night
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Year-Round Hamptons Waterfront, Renovated, Sunsets, Prime Location, Dock

Year-Round Hamptons Waterfront, Renovated, Sunsets, Prime Location, Dock

4 beds 3 baths
PoolA/CWiFiBalcony
$734/night
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Charming Southampton Village Home 4 Bedroom, 2 Bath 5 minutes from the beach

Charming Southampton Village Home 4 Bedroom, 2 Bath 5 minutes from the beach

4 beds 2 baths
PoolA/CWiFiBalcony
$301/night
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Southampton Village Walk to All

Southampton Village Walk to All

1 bed 1 bath
PoolA/CWiFiBalcony
$361/night
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Southampton Village Family Tradition Mint 5BR-5BR. Walkable location.

Southampton Village Family Tradition Mint 5BR-5BR. Walkable location.

5 beds 5 baths
PoolA/CWiFiBalcony
$1,455/night
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Southampton 1 Block From Village, Lovely 4-Bedroom

Southampton 1 Block From Village, Lovely 4-Bedroom

4 beds 3 baths
PoolA/CWiFiBalcony
$632/night
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Spacious Southampton Village Home Walking Distance to Town, Private Pool,...

Spacious Southampton Village Home Walking Distance to Town, Private Pool,...

4 beds 4 baths
PoolA/CWiFiBalcony
$1,894/night
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Perfect SouthHampton getaway

Perfect SouthHampton getaway

3 beds 2 baths
PoolA/CWiFiBalcony
$1,149/night
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Cozy 3 Bedroom Southampton Village Oasis

Cozy 3 Bedroom Southampton Village Oasis

3 beds 1 bath
PoolA/CWiFiBalcony
$653/night
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Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom

4 beds 3 baths
PoolA/CWiFiBalcony
$1,073/night
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1 min drive to Ocean beaches and to Southampton village.

1 min drive to Ocean beaches and to Southampton village.

6 beds 5 baths
PoolA/CWiFiBalcony
$2,960/night
View Details → Book on VRBO
Newly remodeled Southampton Village Retreated with heated pool & tennis courts.

Newly remodeled Southampton Village Retreated with heated pool & tennis courts.

4 beds 4 baths
PoolA/CWiFiBalcony
$715/night
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Charming Village home in the heart of Southampton

Charming Village home in the heart of Southampton

3 beds 2 baths
PoolA/CWiFiBalcony
$396/night
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Southampton Village Luxury with Pool House Spa - Guest Cottage. Walk to Town!

Southampton Village Luxury with Pool House Spa - Guest Cottage. Walk to Town!

4 beds 6 baths
PoolA/CWiFiBalcony
$2,144/night
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Private Village Home-South Of Hill Street, Walk To Coopers Beach/Village

Private Village Home-South Of Hill Street, Walk To Coopers Beach/Village

5 beds 2 baths
PoolA/CWiFiBalcony
$777/night
View Details → Book on VRBO
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

7 beds 7 baths
PoolA/CWiFiBalcony
$2,804/night
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Beautiful Southampton Village/Fall Heated pool!

Beautiful Southampton Village/Fall Heated pool!

4 beds 2 baths
PoolA/CWiFiBalcony
$1,806/night
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Gorgeously Renovated SH Village 5 bd w/ Large Pool

Gorgeously Renovated SH Village 5 bd w/ Large Pool

5 beds 4 baths
PoolA/CWiFiBalcony
$1,505/night
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Luxury Southampton Village House

Luxury Southampton Village House

4 beds 4 baths
PoolA/CWiFiBalcony
$1,939/night
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Walk to the Village! Charming modern farmhouse.

Walk to the Village! Charming modern farmhouse.

3 beds 2 baths
PoolA/CWiFiBalcony
$1,887/night
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Hamptons Style. Close to village restaurants, shops and ocean beach!

Hamptons Style. Close to village restaurants, shops and ocean beach!

7 beds 7 baths
PoolA/CWiFiBalcony
$3,214/night
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Recently Renovated, Inviting Terrace Overlooking Pool, Minutes Away from...

Recently Renovated, Inviting Terrace Overlooking Pool, Minutes Away from...

4 beds 3 baths
PoolA/CWiFiBalcony
$1,435/night
View Details → Book on VRBO
Southampton Village 5 Bedroom Estate, Near Beaches & Village @Lee & Ox Pasture

Southampton Village 5 Bedroom Estate, Near Beaches & Village @Lee & Ox Pasture

5 beds 4 baths
PoolA/CWiFiBalcony
$2,324/night
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Home page of Southampton Village

Home page of Southampton Village

3 beds 2 baths
PoolA/CWiFiBalcony
$702/night
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Southampton estate with saltwater pool, chefs kitchen, vast lawn,...

Southampton estate with saltwater pool, chefs kitchen, vast lawn,...

9 beds 7 baths
PoolA/CWiFiBalcony
$2,750/night
View Details → Book on VRBO
NEW Charming Southampton Village Beach House 5 min from Beach & Town.

NEW Charming Southampton Village Beach House 5 min from Beach & Town.

3 beds 3 baths
PoolA/CWiFiBalcony
$1,472/night
View Details → Book on VRBO
New Southampton Village Gem. 6 bedroom, 6 + bath and 5 minutes drive to beach.

New Southampton Village Gem. 6 bedroom, 6 + bath and 5 minutes drive to beach.

6 beds 7 baths
PoolA/CWiFiBalcony
$4,415/night
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Stunning House: Tennis & Pool in Southampton Estate section

Stunning House: Tennis & Pool in Southampton Estate section

6 beds 7 baths
PoolA/CWiFiBalcony
$5,437/night
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Southampton Village Gem

Southampton Village Gem

3 beds 3 baths
PoolA/CWiFiBalcony
$1,537/night
View Details → Book on VRBO
Open Floor Plan, Spacious and Private Backyard with Patio and Pool, Close...

Open Floor Plan, Spacious and Private Backyard with Patio and Pool, Close...

4 beds 3 baths
PoolA/CWiFiBalcony
$960/night
View Details → Book on VRBO
Summer Rental with Private Heated Pool &Tennis Near Beach & Village

Summer Rental with Private Heated Pool &Tennis Near Beach & Village

3 beds 3 baths
PoolA/CWiFiBalcony
$1,003/night
View Details → Book on VRBO
Fantastic Cottage in Southampton, 2 miles to top beaches and to the town center.

Fantastic Cottage in Southampton, 2 miles to top beaches and to the town center.

4 beds 3 baths
PoolA/CWiFiBalcony
$2,320/night
View Details → Book on VRBO
Beautiful Southampton Village Home, Perfect for Families with Private Pool...

Beautiful Southampton Village Home, Perfect for Families with Private Pool...

6 beds 5 baths
PoolA/CWiFiBalcony
$5,784/night
View Details → Book on VRBO

Showing 48 of 169 properties

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