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

Southampton Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Southampton vacation rentals

1. Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Southampton
9.6 out of 10, Exceptional, (8 reviews)
"great experience"
United States
Jordan
The price is CA $488
CA $819 total
includes taxes & fees
Aug 10 - Aug 11
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

2. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (5 reviews)
"perfect for families"
United States
Okito H.
The price is CA $878
CA $1,874 total
includes taxes & fees
Aug 12 - Aug 13
Minutes from the beach, brand new 4 bedroom

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

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is CA $1,087
CA $1,946 total
includes taxes & fees
Sep 9 - Sep 10
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

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

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Southampton
10.0 out of 10, Exceptional, (2 reviews)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
United States
Beverly J.
The price is CA $962
CA $1,801 total
includes taxes & fees
Aug 31 - Sep 1
Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

5. Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
10.0 out of 10, Exceptional, (4 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 CA $976
CA $2,002 total
includes taxes & fees
Sep 7 - Sep 8
Minutes from the beach, brand new 3 bedroom

6. 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 CA $2,591
CA $3,891 total
includes taxes & fees
Aug 24 - Aug 25
Newly Renovated Pristine Southampton Colonial

7. 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 CA $5,060
CA $6,908 total
includes taxes & fees
Sep 8 - Sep 9
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

8. Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is CA $376
CA $957 total
includes taxes & fees
Sep 7 - Sep 8
Seabreeze #3 Cozy Cottage steps to the beach

9. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (5 reviews)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is CA $223
CA $473 total
includes taxes & fees
Aug 16 - Aug 17
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

10. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"⭐⭐⭐⭐⭐ 100/10 – An unforgettable romantic getaway! We had an amazing stay at this glamping site and spent two wonderful, romantic days here. The atmosphere was peaceful, cozy, and incredibly relaxing. Surrounded by nature, we enjoyed the fresh air, breathtaking sunsets, and quiet evenings that created memories we’ll always cherish. Everything was clean, comfortable, and thoughtfully prepared. The staff was exceptionally kind, welcoming, and always ready to help, which made our stay even more...
United States
Malika
The price is CA $300
CA $454 total
includes taxes & fees
Aug 16 - Aug 17
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

11. Safari Tent Glamping,S9-CedarPt, East Hampton, NY

Safari Tent Glamping,S9-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (3 reviews)
"It was relaxing and beautiful - a perfect and affordable getaway from the city! Also great proximity to so many fun things."
United States
Carolyn
The price is CA $270
CA $415 total
includes taxes & fees
Aug 11 - Aug 12
Safari Tent Glamping,S9-CedarPt, East Hampton, NY

12. Safari Tent Glamping,S2-CedarPt, East Hampton, NY

Safari Tent Glamping,S2-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Comfortable bed and beautiful surroundings"
United States
Matthew
The price is CA $300
CA $454 total
includes taxes & fees
Aug 16 - Aug 17
Safari Tent Glamping,S2-CedarPt, East Hampton, NY

13. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (281 reviews)
"Great place!"
United States
Christine
The price is CA $427
CA $612 total
includes taxes & fees
Sep 9 - Sep 10
Cliffside Resort Condominiums

14. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
The price is CA $453
CA $909 total
includes taxes & fees
Aug 10 - Aug 11
Lovely studio with AC in charming Sag Harbor

15. 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 CA $788
CA $1,338 total
includes taxes & fees
Aug 10 - Aug 11
Immaculate Waterfront 2 bedroom!

16. Aqua Vista

Aqua Vista
Pipes Cove
9.8 out of 10, Exceptional, (40 reviews)
"Nice clean space, well appointed and easy walking access to downtown area."
United States
Molly G.
The price is CA $272
CA $532 total
includes taxes & fees
Sep 1 - Sep 2
Aqua Vista

17. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (44 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is CA $438
CA $500 total
includes taxes & fees
Sep 9 - Sep 10
North Fork Resort

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

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, Exceptional, (26 reviews)
"Everything was in order. When there were a couple of very minor glitches, the manager of the property was immediately responsive - and glitch gone, fast. This was one of the smoothest VRBO experiences we've had, and we've had many."
United States
Carola C.
The price is CA $595
CA $2,894 total
includes taxes & fees
Aug 10 - Aug 11
Villa Luz Family Home w/ heated pool & jacuzzi

19. Hamptons Tiana Bay Oasis

Hamptons Tiana Bay Oasis
Hampton Bays
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed this newly renovated home and had a wonderful time. Beautiful pool and grounds. "
United States
Anonymous traveller
The price is CA $1,079
CA $1,917 total
includes taxes & fees
Sep 2 - Sep 3
Hamptons Tiana Bay Oasis

20. Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (18 reviews)
"Amazing views, beautiful property and pet friendly! Clean, well equipped."
United States
Ana B.
The price is CA $1,475
CA $3,331 total
includes taxes & fees
Aug 10 - Aug 11
Black Swan Beachfront Home with Jacuzzi year round
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Southampton Hotel Reviews

Find out more about Southampton

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Southampton. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Southampton?

Yes, you can find vacation rentals in Southampton close to Southampton Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Southampton. Make sure you have time to check out the museums and festivals during your trip.

What are some of the best vacation rentals in Southampton?

Peaceful and Private 4-Bedroom Home in Southampton: Visitors like this Southampton vacation home rental. It offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub. Some other top choices in Southampton are Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!⛱️ and Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping.

How many vacation rentals are there in Southampton?

Expedia has 504 vacation rentals for your stay in Southampton.

What can I see and do in Southampton?

Enjoy the outdoors at Cooper's Beach and Shinnecock East County Park, or simply take in cultural attractions like Shinnecock Nation Cultural Center and Museum and Halsey House. Other places in town to visit include Southampton Arts Center and North Main Street Historic District.

What are vacation rentals like in Southampton?

Vacation rentals are private properties you can reserve for a short or long stay in Southampton. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.