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Our top choices for Southampton vacation homes

1. Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
10.0 out of 10, Exceptional, (5 reviews)
"Great location. Loved the yard but for small pets the fence has some areas they could get under but overall it worked out. Just kept an eye on them.House very clean, comfortable. Host communication was excellent and would highly recommend for a visit to Southampton. Easy walk into town."
United States
Kathy B.
The price is ¥78,745
¥175,797 total
includes taxes & fees
Nov 9 - Nov 10
Minutes from the beach, brand new 3 bedroom

2. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
United States
Okito H.
The price is ¥70,871
¥166,078 total
includes taxes & fees
Nov 9 - Nov 10
Minutes from the beach, brand new 4 bedroom

3. Newly Renovated Pristine Southampton Colonial

Newly Renovated Pristine Southampton Colonial
Southampton
9.8 out of 10, Exceptional, (12 reviews)
"Great property, worked perfectly for my crew that was in town for an event. Great communication with Brian the owner and very easy stay. Would stay again!"
United States
Brian M.
The price is ¥141,599
¥219,716 total
includes taxes & fees
Nov 12 - Nov 13
Newly Renovated Pristine Southampton Colonial

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

COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
Southampton
9.2 out of 10, Wonderful, (29 reviews)
"I loved the area and the home was beautiful and very spacious."
United States
Melissa
The price is ¥356,209
¥462,241 total
includes taxes & fees
Nov 9 - Nov 10
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

5. Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (16 reviews)
"A great place to stay in Southampton!"
United States
Sarah
The price is ¥355,479
¥456,332 total
includes taxes & fees
Nov 12 - Nov 13
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

6. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ¥9,621
¥180,085 total
includes taxes & fees
Nov 10 - Nov 11
Jacuzzi year-round - Villa Luz Private Home

7. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 reviews)
"What an amazing view!!!!! Great place to stay!!! Highly recommend the Black Swan home."
United States
John M.
The price is ¥14,210
¥195,719 total
includes taxes & fees
Nov 12 - Nov 13
Beachfront Jacuzzi All Year - Black Swan Home

8. Stunning shingled Water Mill estate featuring a private heated pool and...

Stunning shingled Water Mill estate featuring a private heated pool and...
Water Mill
10.0 out of 10, Exceptional, (2 reviews)
"House was very well maintained. Back pool area was spacious and great for entertainment."
United States
Michael C.
Stunning shingled Water Mill estate featuring a private heated pool and...

9. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (2 reviews)
"The property was great for our Hamptons trip! Very clean and comfortable and communication was great"
United States
Katie B.
The price is ¥44,885
¥87,990 total
includes taxes & fees
Nov 15 - Nov 16
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

10. Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is ¥42,522
¥86,007 total
includes taxes & fees
Nov 9 - Nov 10
Immaculate Waterfront 2 bedroom!

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

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is ¥82,589
¥170,829 total
includes taxes & fees
Nov 7 - Nov 8
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

12. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!
Wainscott
10.0 out of 10, Exceptional, (34 reviews)
"We loved this home and location! The home is so beautifully appointed and clean. It had everything you would ever need for a wonderful time with family and friends. The hosts were extremely responsive and easy to work with. We would go back in a heartbeat!"
United States
Suzanne B.
The price is ¥130,118
¥313,298 total
includes taxes & fees
Nov 12 - Nov 13
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!!

13. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is ¥11,533
¥213,459 total
includes taxes & fees
Nov 9 - Nov 10
Year round Jacuzzi - Blackberry East Hampton Home

14. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is ¥13,539
¥36,455 total
includes taxes & fees
Nov 10 - Nov 11
The SandPiper

15. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (52 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ¥14,962
¥38,146 total
includes taxes & fees
Nov 9 - Nov 10
Aqua Vista

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

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ¥20,552
¥54,789 total
includes taxes & fees
Nov 9 - Nov 10
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

17. Prime location, walk to all, cozy cottage WHB

Prime location, walk to all, cozy cottage WHB
Westhampton Beach
10.0 out of 10, Exceptional, (4 reviews)
"Property was in easy walking distance from the village which made morning coffee runs a breeze. Very clean accommodations and large back yard."
United States
Matt S.
The price is ¥46,713
¥92,446 total
includes taxes & fees
Nov 10 - Nov 11
Prime location, walk to all, cozy cottage WHB

18. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is ¥30,711
¥67,474 total
includes taxes & fees
Nov 11 - Nov 12
Beach Block Hideaway

19. Spacious 5-bedroom house with Private Beach and Wide Open Bay Views

Spacious 5-bedroom house with Private Beach and Wide Open Bay Views
Hampton Bays
The price is ¥170,089
¥318,300 total
includes taxes & fees
Nov 13 - Nov 14
Spacious 5-bedroom house with Private Beach and Wide Open Bay Views

20. Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (7 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is ¥188,988
¥223,477 total
includes taxes & fees
Nov 7 - Nov 8
Cozy Hamptons Escape 3BR Minutes From Beach!
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.

Learn more about Southampton

Pristine beaches stretch for miles along this Hamptons gem where celebrities and locals mingle at waterfront seafood spots. Explore historic mansions and boutique shops in the village, then catch a spectacular sunset from Cooper's Beach with a local lobster roll.

A welcome sign for the village of Southampton, established in 1640, with a cyclist on the road.

Top reviews in Southampton