Town of Southampton Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Top Holiday Rentals Destinations in Town of Southampton

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (166)
"Perfect family home"
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (16)
"Had the best girls weekend with old college roommates! The house is stunning and incredibly clean. Was well stocked with everything we needed for our stay. Great location as well for checking out downtown, the beach, wineries, etc. "
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Hamptons - Pool & Private Tennis Court, Hot Tub, 2 Pickleball Courts

10.0 out of 10, Exceptional, (14)
"Really great spot. Quiet, great rooms and bathrooms. Pool and hot tub were perfect. Communication was great. Would definitely stay again! "
Hamptons - Pool & Private Tennis Court, Hot Tub, 2 Pickleball Courts

Beautiful Family Home Nestled In The Heart Of Sagaponack

10.0 out of 10, Exceptional, (30)
"Great space and location. We loved the house and enjoyed our stay. "
Beautiful Family Home Nestled In The Heart Of Sagaponack

Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub

9.6 out of 10, Exceptional, (95)
"We had an absolutely amazing time at Brian’s home. The pool was beautiful and the hot tub was perfect! The home was spacious and the deck was perfect for grilling and hanging outside. This home was great for a big family to get together and have a relaxing fun weekend together. We would definitely recommend and would love to go back ! "
Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub

5 bedroom Private Family Get Away w/ Heated Pool

10.0 out of 10, Exceptional, (13)
"We were a group age 3 to 75! The house was clean, well stocked and things for everyone’s interest. Our host, Carrie, was kind and responsive. It will be a beautiful memory of spending time with our children and grandchildren. "
5 bedroom Private Family Get Away w/ Heated Pool

Fall in the🌅beautiful sunsets

10.0 out of 10, Exceptional, (24)
"Margaret is just wonderful. We felt like we were staying at a dear family member’s home. Stayed in her very private upstairs suite and it was perfect for me, my wife and our pup. He had a blast running around the yard, meeting the chickens going to the bay beach etc. We had the best time! Thank you Margaret!!"
Fall in the🌅beautiful sunsets

2 Bedroom Hamptons Waterfront Cottage Rental

10.0 out of 10, Exceptional, (10)
"Everything first class. Air co and heat units in each tooth Everything thing you might need for a great vacation "
2 Bedroom Hamptons Waterfront Cottage Rental

Hamptons apartment getaway

10.0 out of 10, Exceptional, (1)
"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "
The price is AU$354
includes taxes & fees
29 Nov - 30 Nov
Hamptons apartment getaway

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

Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

10.0 out of 10, Exceptional, (18)
"Exceptional property, extremely well designed, location is outstanding; it is a true Hamptons Estate fit ideally for family stays and relaxing experience. "
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

Gorgeous private Hamptons house with pool and volleyball court

8.4 out of 10, Very good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court

Summer getaway

9.2 out of 10, Wonderful, (10)
"Overall, we had a terrific time at the house. Thank-you so much Andres for sharing your home with us. Getting there, checking in, all simple and easy. House was very well stocked. There was plenty of room for the eight of us. The beds were all comfortable. The deck was delightful. A couple of minor things that we had happen, or noticed that might want to be addressed. Given the house is controlled by Alexa, some detailed instructions as to how to work with "her" might be a good idea for...
Summer getaway

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

10.0 out of 10, Exceptional, (33)
"The house was perfect, a home away from home located in a nice quiet area, with stores and restaurants close by. House was clean, spacious and stocked with the essentials. The kids loved the pool and the ping pong table. Thank you Val for the perfect weekend, hope to see you next Summer!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

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

Sag Harbor Village Chic with water views

9.8 out of 10, Exceptional, (8)
"The lilacs were in bloom and we could walk to town for eggs and milk. A relaxing stay in a beautiful town."
Sag Harbor Village Chic with water views

Beautifully Restored Barn, Open First Floor Plan, Historic Charm and...

10.0 out of 10, Exceptional, (23)
"Loved it all "
Beautifully Restored Barn, Open First Floor Plan, Historic Charm and...

Yellowstone In The Hamptons ~ 18-Acre Estate Surrounded By A Nature Preserve

10.0 out of 10, Exceptional, (17)
"I really felt like we went to heaven! This is the most magnificent, tranquil and breathtaking property we have ever seen! Every detail from the minute you drive in is absolute PERFECTION! This one of a kind western Wonderland with stunning design and décor, the spectacular grounds, the beautiful horses, and the wonderful wildlife made this a once in a lifetime experience that we will never forget! Plus: We were treated like royalty with every one of our needs attended to as if we were staying...
Yellowstone In The Hamptons ~ 18-Acre Estate Surrounded By A Nature Preserve

Labor day special! Gorgeous Hamptons vacation property with heated Pool

9.8 out of 10, Exceptional, (16)
"We had an incredible experience at Maria’s place. The house itself was great with lots of bedrooms and bathrooms to accommodate a large group but also a central great room which was a great place for us to hang out and relax together. Outside the pool was amazing and warm, and the tennis court was such a nice addition to the house. Everything was well stocked with lots of cookware, plates, etc. Maria was great and very communicative throughout the process with lots of local recommendations too....
Labor day special! Gorgeous Hamptons vacation property with heated Pool

Heated Pool and Tennis Court

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay with our family over Thanksgiving. The house was absolutely perfect and Amanda was an amazing host!"
Heated Pool and Tennis Court
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.
Don't see what you're looking for?
See all available properties in Town of Southampton
Save an average of 15% on thousands of hotels when you're signed in
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.