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Compare 200 Vacation Homes in Southampton with updated reviews, rates, and availability.

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Sprawling pool with outdoor kitchen
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
10.0 out of 10, Exceptional, (15)
"Our group of friends stayed at this house for a long weekend in October 2024. The house is just as good or better than the pictures in the listing. Very clean and updated inside and out. Most importantly, the bathrooms and kitchen are clean and updated. And the huge backyard with pool, hot tub, and outdoor shower takes this house to the next level. The backyard space is great for families, small groups, or anyone looking for a quiet private space to relax. The owner/manager was very...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Welcome to the J Luxury Southampton Estate w/Pool
Welcome to the J
Welcome to the J Luxury Southampton Estate w/Pool
9.8 out of 10, Exceptional, (30)
"Joe was an amazing host - always responsive from the moment of booking throughout the entire stay. The kitchen was a chef's dream - spacious and stocked with every appliance, seasoning, etc you can think of. We were a group of 8 and cooked family dinners each night. The highlight of the property was most definitely the deck, which was beautifully decorated and with a perfect amount of seating. Neighborhood was very walkable and it was a very short drive to the beach! I would note that there are...
Welcome to the J Luxury Southampton Estate w/Pool
Southampton Village Luxury with Pool House Spa - Guest Cottage. Walk to Town!
Private kitchen
Southampton Village Luxury with Pool House Spa - Guest Cottage. Walk to Town!
10.0 out of 10, Exceptional, (9)
"Great house close to Main Street. The sauna and pool were a big hit with our group!"
Southampton Village Luxury with Pool House Spa - Guest Cottage. Walk to Town!
Secluded Southampton Home That Has It All
Living area
Secluded Southampton Home That Has It All
10.0 out of 10, Exceptional, (1)
"This was a perfect getaway for a multigenerational family reunion! It's a beautifully maintained property. The bathroom to bedroom ratio was great for many families/couples. Great amenities included a heated pool and jacuzzi, and it's ideally located with easy access to Southampton and Sag Harbor downtown areas. Bob was a wonderful host and easy to reach. I recommend this place for anyone planning a family getaway. "
Secluded Southampton Home That Has It All
Beautiful Southampton Village home, new reno, Heated pool!
Pool
Beautiful Southampton Village home, new reno, Heated pool!
10.0 out of 10, Exceptional, (32)
"Stayed with my elderly parents and teenage kids. Great Southampton location, well stocked house from kitchen to beach needs. Loved the bikes! "
Beautiful Southampton Village home, new reno, Heated pool!
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Pool
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
10.0 out of 10, Exceptional, (10)
"Felt very welcome in a lovely home, did not feel fake or pretend. Well appointed with tons of space for our group. Loved the spacious backyard and had a great time cooking and relaxing outside. Would stay here again without question. Very close to town, didn't need to drive if we didn't want to. "
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Hamptons Modern Retreat NEW CONS
Hamptons Modern Retreat NEW CONS
10.0 out of 10, Exceptional, (7)
"This house is as advertised – very comfortable for a large group. We are a group of 12 and everyone fit at the dining table. The bedrooms we very nice – bed linens amazing! Pool was closed for the season but the hot tub was open and very clean. The outside seating is comfortable. We did run out of gas for the grill – so check in advance that the tank is full. You will have a great weekend - enjoy! "
Hamptons Modern Retreat NEW CONS
5BR, Luxury Home, Pool, Large Yard , Close to Beach & Town
Backyard
5BR, Luxury Home, Pool, Large Yard , Close to Beach & Town
9.6 out of 10, Exceptional, (10)
"The house was great for our family vacation. The pool was perfect to hang out when not at the beach. Fully stocked and comfortable. Would definitely recommend and stay again."
5BR, Luxury Home, Pool, Large Yard , Close to Beach & Town
Newly Renovated Southampton Getaway House
Pool
Newly Renovated Southampton Getaway House
10.0 out of 10, Exceptional, (3)
"This house is amazing. The space was perfect for a family week. Great open kitchen and hang out space including plenty of games and activities. The property is lovely with a great pool and plenty of space. We loved it and would easily return."
Newly Renovated Southampton Getaway House
Minutes from the beach, brand new 4 bedroom
Outdoor dining
Minutes from the beach, brand new 4 bedroom
The price is SAR 3,696
SAR 5,924 total
includes taxes & fees
10 Nov - 11 Nov
Minutes from the beach, brand new 4 bedroom
Southampton Village Family Tradition Mint 5BR-5BR. Walkable location.
Pool
Southampton Village Family Tradition Mint 5BR-5BR. Walkable location.
10.0 out of 10, Exceptional, (12)
"We had a wonderful stay at this beautiful home. Clean, beautifully decorated and all the amenities for a family vacation . The host was fabulous and shared recommendations for dinners and places to visit. We would definitely stay here again!"
Southampton Village Family Tradition Mint 5BR-5BR. Walkable location.
Private 2.1 acre gated home with heated pool and tennis & pickleball court
Exterior
Private 2.1 acre gated home with heated pool and tennis & pickleball court
10.0 out of 10, Exceptional, (17)
"With a baby we needed a place with enough entertainment, so we didn’t have to go out much. This place has ALL of that and more. We loved it. We cooked, grilled, swam, played tennis, pickleball, ping pong, pool; all at the house. It was perfect."
Private 2.1 acre gated home with heated pool and tennis & pickleball court
Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis
Private pool
Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis
9.8 out of 10, Exceptional, (25)
"Ken was great and easy to work with. The house was nice and perfect for our stay!"
Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis
Newly Renovated Southampton Home with Heated Pool
Pool
Newly Renovated Southampton Home with Heated Pool
7.6 out of 10, Good, (4)
"Wonderful home. Perfect for family and entertaining. "
Newly Renovated Southampton Home with Heated Pool
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Pool
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
9.6 out of 10, Exceptional, (7)
"The house is in a great location but was definitely showing some wear and tear. Things like the pool having damage around the sides, a lot of dishes/cutlery missing, broken glass from prior guests behind chairs, etc. The house could use a walk through with a handyman to fix the issues popping up with fixtures and finishes and a restock on household basics."
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Open LR and Dining
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (98)
"The house is immaculate, stylishly decorated, perfectly located and wonderfully outfitted from kitchen to beach. The very best of VRBO. "
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Sprawling Southampton Home: Private Pool, Game Room
Large private pool for the whole group to enjoy!
Sprawling Southampton Home: Private Pool, Game Room
9.0 out of 10, Wonderful, (44)
"My family and I had a wonderful stay at this property. The house was well-situated in a quiet neighborhood - very private, surrounded by trees and a few wild turkeys. There were many amenities that made our stay enjoyable from the large patio and pool, 3 full baths in the main house, one of which had an amazing shower system with body spray, and a designated work area for those that can’t leave work behind. Communication with the property manager was easy and Debbie was very helpful and...
Sprawling Southampton Home: Private Pool, Game Room
Stellar Ocean Front Hamptons Getaway
Beach
Stellar Ocean Front Hamptons Getaway
Stellar Ocean Front Hamptons Getaway
Charming Village home in the heart of Southampton
Pool
Charming Village home in the heart of Southampton
10.0 out of 10, Exceptional, (19)
"Great location, clean, easy checkin, slept 7 comfortably"
Charming Village home in the heart of Southampton
Southampton estate with oversized pool, chefs kitchen, vast lawn,...
Outdoor dining
Southampton estate with oversized pool, chefs kitchen, vast lawn,...
Southampton estate with oversized pool, chefs kitchen, vast lawn,...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Southampton

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Sprawling pool with outdoor kitchen
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
10.0 out of 10, Exceptional, (15)
"Our group of friends stayed at this house for a long weekend in October 2024. The house is just as good or better than the pictures in the listing. Very clean and updated inside and out. Most importantly, the bathrooms and kitchen are clean and updated. And the huge backyard with pool, hot tub, and outdoor shower takes this house to the next level. The backyard space is great for families, small groups, or anyone looking for a quiet private space to relax. The owner/manager was very...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Beautiful Southampton Home One Block from Shinnecock Bay, Town Shopping,...
Pool
Beautiful Southampton Home One Block from Shinnecock Bay, Town Shopping,...
9.4 out of 10, Exceptional, (3)
"We loved being together and the house and pool made it ideal for two weeks with an infant. We wished that there was better information/communication about lawn and pool service, pest treatment and trash pick-up. We were also bit disappointed that the outdoor table was not replace and we could not do any outdoor dinners."
Beautiful Southampton Home One Block from Shinnecock Bay, Town Shopping,...
Secluded Southampton Home That Has It All
Living area
Secluded Southampton Home That Has It All
10.0 out of 10, Exceptional, (1)
"This was a perfect getaway for a multigenerational family reunion! It's a beautifully maintained property. The bathroom to bedroom ratio was great for many families/couples. Great amenities included a heated pool and jacuzzi, and it's ideally located with easy access to Southampton and Sag Harbor downtown areas. Bob was a wonderful host and easy to reach. I recommend this place for anyone planning a family getaway. "
Secluded Southampton Home That Has It All
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.