We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals with Pools in Southampton

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
0 rentals in Southampton.
The following properties match some of your filters:
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to, holiday rental in Southampton
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to, holiday rental in Southampton
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to, holiday rental in Southampton

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Gorgeous private Hamptons house with pool and volleyball court, holiday rental in Southampton
Gorgeous private Hamptons house with pool and volleyball court, holiday rental in Southampton
Gorgeous private Hamptons house with pool and volleyball court, holiday rental in Southampton

Gorgeous private Hamptons house with pool and volleyball court

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Come to the Hamptons and Getaway!, holiday rental in Southampton
Come to the Hamptons and Getaway!, holiday rental in Southampton
Come to the Hamptons and Getaway!, holiday rental in Southampton

Come to the Hamptons and Getaway!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!, holiday rental in Southampton
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!, holiday rental in Southampton
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!, holiday rental in Southampton

Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!, holiday rental in Southampton
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!, holiday rental in Southampton
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!, holiday rental in Southampton

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach, holiday rental in Southampton
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach, holiday rental in Southampton
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach, holiday rental in Southampton

Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Beautiful Garden with pool & koi fish pond - 2 cottages fully renovated, holiday rental in Southampton
Beautiful Garden with pool & koi fish pond - 2 cottages fully renovated, holiday rental in Southampton
Beautiful Garden with pool & koi fish pond - 2 cottages fully renovated, holiday rental in Southampton

Beautiful Garden with pool & koi fish pond - 2 cottages fully renovated

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Walk to the Village! Charming modern farmhouse., holiday rental in Southampton
Walk to the Village! Charming modern farmhouse., holiday rental in Southampton
Walk to the Village! Charming modern farmhouse., holiday rental in Southampton

Walk to the Village! Charming modern farmhouse.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Charming Southampton Village Home  4 Bedroom, 2 Bath 
5 minutes from the beach, holiday rental in Southampton
Charming Southampton Village Home  4 Bedroom, 2 Bath 
5 minutes from the beach, holiday rental in Southampton
Charming Southampton Village Home  4 Bedroom, 2 Bath 
5 minutes from the beach, holiday rental in Southampton

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Charming Hampton Bays Home 5 Mi to Cooper’s Beach, holiday rental in Southampton
Charming Hampton Bays Home 5 Mi to Cooper’s Beach, holiday rental in Southampton
Charming Hampton Bays Home 5 Mi to Cooper’s Beach, holiday rental in Southampton

Charming Hampton Bays Home 5 Mi to Cooper’s Beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Beautiful Vacation Home in Hampton Bays walking distance to Peconic Bay Beaches!, holiday rental in Southampton
Beautiful Vacation Home in Hampton Bays walking distance to Peconic Bay Beaches!, holiday rental in Southampton
Beautiful Vacation Home in Hampton Bays walking distance to Peconic Bay Beaches!, holiday rental in Southampton

Beautiful Vacation Home in Hampton Bays walking distance to Peconic Bay Beaches!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms, holiday rental in Southampton
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms, holiday rental in Southampton
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms, holiday rental in Southampton

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Cozy home in Hampton Bays near Ponquogue beach, holiday rental in Southampton
Cozy home in Hampton Bays near Ponquogue beach, holiday rental in Southampton
Cozy home in Hampton Bays near Ponquogue beach, holiday rental in Southampton

Cozy home in Hampton Bays near Ponquogue beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Newly Listed - Updated Carriage House Apt - Centrally Located, holiday rental in Southampton
Newly Listed - Updated Carriage House Apt - Centrally Located, holiday rental in Southampton
Newly Listed - Updated Carriage House Apt - Centrally Located, holiday rental in Southampton

Newly Listed - Updated Carriage House Apt - Centrally Located

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Hamptons Waterfront- On A Sandy Beach- Relax & Getaway! (SH), holiday rental in Southampton
Hamptons Waterfront- On A Sandy Beach- Relax & Getaway! (SH), holiday rental in Southampton
Hamptons Waterfront- On A Sandy Beach- Relax & Getaway! (SH), holiday rental in Southampton

Hamptons Waterfront- On A Sandy Beach- Relax & Getaway! (SH)

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Beach Hot tub Enjoy a getaway. Winery near, holiday rental in Southampton
Beach Hot tub Enjoy a getaway. Winery near, holiday rental in Southampton
Beach Hot tub Enjoy a getaway. Winery near, holiday rental in Southampton

Beach Hot tub Enjoy a getaway. Winery near

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Stunning Bayfront Views, holiday rental in Southampton
Stunning Bayfront Views, holiday rental in Southampton
Stunning Bayfront Views, holiday rental in Southampton

Stunning Bayfront Views

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Luxury Southampton Village House, holiday rental in Southampton
Luxury Southampton Village House, holiday rental in Southampton
Luxury Southampton Village House, holiday rental in Southampton

Luxury Southampton Village House

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Southampton Village So of Hwy with Fireplace - water View, holiday rental in Southampton
Southampton Village So of Hwy with Fireplace - water View, holiday rental in Southampton
Southampton Village So of Hwy with Fireplace - water View, holiday rental in Southampton

Southampton Village So of Hwy with Fireplace - water View

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Hampton's Retreat, holiday rental in Southampton
Hampton's Retreat, holiday rental in Southampton
Hampton's Retreat, holiday rental in Southampton

Hampton's Retreat

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14, holiday rental in Southampton
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14, holiday rental in Southampton
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14, holiday rental in Southampton

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Modern Beach house-5 minutes from the beach!, holiday rental in Southampton
Modern Beach house-5 minutes from the beach!, holiday rental in Southampton
Modern Beach house-5 minutes from the beach!, holiday rental in Southampton

Modern Beach house-5 minutes from the beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Beautiful resort style backyard with newly added professional PICKLEBALL COURT., holiday rental in Southampton
Beautiful resort style backyard with newly added professional PICKLEBALL COURT., holiday rental in Southampton
Beautiful resort style backyard with newly added professional PICKLEBALL COURT., holiday rental in Southampton

Beautiful resort style backyard with newly added professional PICKLEBALL COURT.

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Private Beach front Home, holiday rental in Southampton
Private Beach front Home, holiday rental in Southampton
Private Beach front Home, holiday rental in Southampton

Private Beach front Home

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Studio on Tianna Bay (Memorial Day - Labor Day), holiday rental in Southampton
Studio on Tianna Bay (Memorial Day - Labor Day), holiday rental in Southampton
Studio on Tianna Bay (Memorial Day - Labor Day), holiday rental in Southampton

Studio on Tianna Bay (Memorial Day - Labor Day)

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Southampton Home #5, holiday rental in Southampton
Southampton Home #5, holiday rental in Southampton
Southampton Home #5, holiday rental in Southampton

Southampton Home #5

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Beautiful Beach Front 1 Bedroom Triplex, holiday rental in Southampton
Beautiful Beach Front 1 Bedroom Triplex, holiday rental in Southampton
Beautiful Beach Front 1 Bedroom Triplex, holiday rental in Southampton

Beautiful Beach Front 1 Bedroom Triplex

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Southampton Home #2, holiday rental in Southampton
Southampton Home #2, holiday rental in Southampton
Southampton Home #2, holiday rental in Southampton

Southampton Home #2

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Southampton Home #1, holiday rental in Southampton
Southampton Home #1, holiday rental in Southampton
Southampton Home #1, holiday rental in Southampton

Southampton Home #1

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Southampton Home #3, holiday rental in Southampton
Southampton Home #3, holiday rental in Southampton
Southampton Home #3, holiday rental in Southampton

Southampton Home #3

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Hampton Chic3 Bedroom 2 Bathrooms with Pool, holiday rental in Southampton
Hampton Chic3 Bedroom 2 Bathrooms with Pool, holiday rental in Southampton
Hampton Chic3 Bedroom 2 Bathrooms with Pool, holiday rental in Southampton

Hampton Chic3 Bedroom 2 Bathrooms with Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Tiny Southampton House on the Bay, holiday rental in Southampton
Tiny Southampton House on the Bay, holiday rental in Southampton
Tiny Southampton House on the Bay, holiday rental in Southampton

Tiny Southampton House on the Bay

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Million Dollar Sunsets Overlooking Bayfront Beach, holiday rental in Southampton
Million Dollar Sunsets Overlooking Bayfront Beach, holiday rental in Southampton
Million Dollar Sunsets Overlooking Bayfront Beach, holiday rental in Southampton

Million Dollar Sunsets Overlooking Bayfront Beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Hamptons getaway - let’s go ! Close to ocean beach-family friendly-walk to bay, holiday rental in Southampton
Hamptons getaway - let’s go ! Close to ocean beach-family friendly-walk to bay, holiday rental in Southampton
Hamptons getaway - let’s go ! Close to ocean beach-family friendly-walk to bay, holiday rental in Southampton

Hamptons getaway - let’s go ! Close to ocean beach-family friendly-walk to bay

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
New Duplex Apartment, holiday rental in Southampton
New Duplex Apartment, holiday rental in Southampton
New Duplex Apartment, holiday rental in Southampton

New Duplex Apartment

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Southampton Village Walk to All, holiday rental in Southampton
Southampton Village Walk to All, holiday rental in Southampton
Southampton Village Walk to All, holiday rental in Southampton

Southampton Village Walk to All

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Expansive Hamptons Mansion!, holiday rental in Southampton
Expansive Hamptons Mansion!, holiday rental in Southampton
Expansive Hamptons Mansion!, holiday rental in Southampton

Expansive Hamptons Mansion!

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Hamptons 2 bedroom with heated pool, holiday rental in Southampton
Hamptons 2 bedroom with heated pool, holiday rental in Southampton
Hamptons 2 bedroom with heated pool, holiday rental in Southampton

Hamptons 2 bedroom with heated pool

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Retro Mid-Century Cottage 1/2 mile to CPI, holiday rental in Southampton
Retro Mid-Century Cottage 1/2 mile to CPI, holiday rental in Southampton
Retro Mid-Century Cottage 1/2 mile to CPI, holiday rental in Southampton

Retro Mid-Century Cottage 1/2 mile to CPI

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Guest House Overlooking Pool, holiday rental in Southampton
Guest House Overlooking Pool, holiday rental in Southampton
Guest House Overlooking Pool, holiday rental in Southampton

Guest House Overlooking Pool

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Stunning Waterfront Beach House, holiday rental in Southampton
Stunning Waterfront Beach House, holiday rental in Southampton
Stunning Waterfront Beach House, holiday rental in Southampton

Stunning Waterfront Beach House

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Chic sunny 2bedroom guest cottage 5 mins from beach and village, holiday rental in Southampton
Chic sunny 2bedroom guest cottage 5 mins from beach and village, holiday rental in Southampton
Chic sunny 2bedroom guest cottage 5 mins from beach and village, holiday rental in Southampton

Chic sunny 2bedroom guest cottage 5 mins from beach and village

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Water mill cottage on a 5 acre estate near  beaches, holiday rental in Southampton
Water mill cottage on a 5 acre estate near  beaches, holiday rental in Southampton
Water mill cottage on a 5 acre estate near  beaches, holiday rental in Southampton

Water mill cottage on a 5 acre estate near beaches

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Southampton Home #4, holiday rental in Southampton
Southampton Home #4, holiday rental in Southampton
Southampton Home #4, holiday rental in Southampton

Southampton Home #4

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Southampton Home #6, holiday rental in Southampton
Southampton Home #6, holiday rental in Southampton
Southampton Home #6, holiday rental in Southampton

Southampton Home #6

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Cottage on the Bay in Hampton Bays, holiday rental in Southampton
Cottage on the Bay in Hampton Bays, holiday rental in Southampton
Cottage on the Bay in Hampton Bays, holiday rental in Southampton

Cottage on the Bay in Hampton Bays

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Hamptons Haven: Sunny 1-bedroom oasis with modern comforts near the bay!, holiday rental in Southampton
Hamptons Haven: Sunny 1-bedroom oasis with modern comforts near the bay!, holiday rental in Southampton
Hamptons Haven: Sunny 1-bedroom oasis with modern comforts near the bay!, holiday rental in Southampton

Hamptons Haven: Sunny 1-bedroom oasis with modern comforts near the bay!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Spacious Hamptons Apartment - Below Ground Level, holiday rental in Southampton
Spacious Hamptons Apartment - Below Ground Level, holiday rental in Southampton
Spacious Hamptons Apartment - Below Ground Level, holiday rental in Southampton

Spacious Hamptons Apartment - Below Ground Level

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
3 Bedroom House 4-5 Month Rental Unfurnished, holiday rental in Southampton
3 Bedroom House 4-5 Month Rental Unfurnished, holiday rental in Southampton
3 Bedroom House 4-5 Month Rental Unfurnished, holiday rental in Southampton

3 Bedroom House 4-5 Month Rental Unfurnished

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Fall in the�beautiful sunsets, holiday rental in Southampton
Fall in the�beautiful sunsets, holiday rental in Southampton
Fall in the�beautiful sunsets, holiday rental in Southampton

Fall in the�beautiful sunsets

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Vrbo.com logo
Showing results 1-50 of 732
Things to DoRestaurantsFlightsTravel StoriesCruisesCar Hire