Southampton Vacation Homes

A beach with a wooden fence, a lifeguard tower, and a house with a balcony overlooking the ocean.

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Our top choices for Southampton holiday homes

1. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

HK$10,546 total

includes taxes & fees

4 Aug - 5 Aug

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

Southampton

Justin

HK$18,323 total

includes taxes & fees

17 Aug - 18 Aug

3. Amazing Southampton Home with Private Heated Pool

Southampton

HK$30,388 total

includes taxes & fees

3 Aug - 4 Aug

Beach nearby, sun-loungers, beach towels

4. Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

Southampton

Beverly J.

HK$10,035 total

includes taxes & fees

9 Aug - 10 Aug

5. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

HK$13,305 total

includes taxes & fees

2 Aug - 3 Aug

6. Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

HK$21,235 total

includes taxes & fees

24 Aug - 25 Aug

7. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

Southampton

Melissa

HK$53,907 total

includes taxes & fees

12 Aug - 13 Aug

8. Hampton Bays Townhouse - Pool, Beach Access

Hampton Bays

Eileen O.

HK$5,062 total

includes taxes & fees

18 Aug - 19 Aug

Coffee/tea maker, fridge, microwave, oven

9. Immaculate Waterfront 2 bedroom!

Hampton Bays

Michael L.

HK$7,374 total

includes taxes & fees

1 Sept - 2 Sept

10. Villa Luz Family Home w/ heated pool & jacuzzi

Hampon Bays

Carola C.

HK$19,184 total

includes taxes & fees

9 Aug - 10 Aug

11. Cozy 5 Bedroom With Wi-fi And Air Condition

Wainscott

HK$15,294 total

includes taxes & fees

2 Aug - 3 Aug

12. Elegant 5-Bedroom Hamptons Home with Private Pool

Hampton Bays

Sarah A.

HK$12,284 total

includes taxes & fees

20 Aug - 21 Aug

13. Cozy Hamptons Escape 3BR Minutes From Beach!

Hampton Bays

Taylor H.

HK$12,284 total

includes taxes & fees

2 Aug - 3 Aug

14. Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Sag Harbor

Nadja B.

15. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Sag Harbor

maria m.

HK$17,742 total

includes taxes & fees

16 Aug - 17 Aug

16. The SandPiper

Pipes Cove

Marie H.

HK$5,071 total

includes taxes & fees

16 Aug - 17 Aug

17. Chic Modern Retreat in the Heart of EH! Pool Open!

East Hampton

Bryan A.

HK$33,501 total

includes taxes & fees

7 Aug - 8 Aug

18. American Beech in Greenport - Petite King Room 7

Greenport

Parent From The Heart, Inc. E.

HK$4,032 total

includes taxes & fees

2 Aug - 3 Aug

19. BlackBerry Private home with jacuzzi yearlong

East Hampton

Suzanne R.

HK$14,897 total

includes taxes & fees

12 Aug - 13 Aug

20. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

Callie E.

HK$6,093 total

includes taxes & fees

26 Aug - 27 Aug

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Top Southampton Hotel Reviews

Harpoon House

10/10 Excellent

"There was no air conditioning at first and it was hot"

The Bentley Hotel Southampton

8/10 Good

"We stayed here a year ago, and when we decided to drive out to the Hamptons, this was our no-brainer choice. It's not a luxury resort, but you're not gonna pay luxury prices. The "room" is truly a suite, with a large living room, which includes a kitchenette -- and a full size refrigerator, not the typical mini. The room is clean, modern and quiet. (we prefer the upper level). Our only negative is that it's really at the very start of what most people consider The Hamptons, so it's a drive -- sometimes considerable -- to get to most places."

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

10/10 Excellent

"Dave was one of the best rental hosts I’ve ever experienced. His communication and kindness was top of the matter. We were able to check in early on Thursday ahead of my sisters arrival (the bride) to get decorations together and prep the house. The pool was even more amazing in photos and we brought floats but there was plenty already there to use. Garbage pick up is on Fridays so we arrived to some full garbage cans outside the house but Dave communicated that and it was no issue. The beds were comfy, plenty of bathrooms and showers for our group of 11. The house was low on paper towels so Dave had some delivered and sent us snacks and goodies as well. The house is close to Main Street and Ubers were super accessible. I would happily come back to this house."

Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

8/10 Good

"Ken was a good host: readily available and communicated well.The property was as advertised. We were a group of college buddies getting together nearly 40 years after graduation. This secluded retreat was ideal for us. The rustic property was clean. There were more than enough beds for our small group of six."

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

10/10 Excellent

"Went to stay in SouthHamptons and booked in March for my trip in August. The price was much lower than some of the other placed I was concerned. The place was excellent location. The only issue I have was that we were so busy during our stay that we didn't get a chance to enjoy the pool or outside of the property. The Host was great and freindly I hope the place is available when I go bock."

Minutes from the beach, brand new 3 bedroom

10/10 Excellent

"We had a wonderful stay! The location was excellent—close to everything we wanted to do while still feeling peaceful and relaxing. Communication with the host was fantastic from start to finish, with quick responses and clear instructions that made everything easy. We really enjoyed our time and would happily stay here again. Highly recommend!"

Minutes from the beach, brand new 4 bedroom

10/10 Excellent

"House was extremely clean, well taken care of and was absolutely ready to go when we got there. Nice quiet neighborhood so don't plan on throwing any ragers here. Maybe only thing to be aware of is plan on getting ice in advance as no ice maker which isn't a surprise as they break constantly under use. A little on the pricy side but you get what you pay for and it's the Hamptons. Thanks for a pretty flawless stay."

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