Southampton Vacation Rentals from $587: Search Short-Term Rentals

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Our top choices for Southampton vacation rentals

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

Southampton

Angelo D.

$514 nightly

Sep 27 - Sep 28

Total with taxes and fees

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

Southampton

Justin

$794 nightly

Oct 21 - Oct 22

Total with taxes and fees

3. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

$1,257 nightly

Sep 22 - Sep 23

Total with taxes and fees

4. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

$1,261 nightly

Oct 1 - Oct 2

Total with taxes and fees

5. Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

$2,364 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

Southampton

Deborah V.

$1,991 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

Southampton

Melissa

$2,524 nightly

Oct 1 - Oct 2

Total with taxes and fees

8. Safari Tent Glamping,S4-CedarPt, East Hampton, NY

East Hampton

$260 nightly

Sep 24 - Sep 25

Total with taxes and fees

9. Seabreeze #3 Cozy Cottage steps to the beach

Hampton Bays

"Camila was very communicative and helpful. The cottage clearly has a history of high traffic, and while it holds a certain rustic charm, it's undeniably showing its age. The property feels quite worn and tired, with fixtures and furnishings having seen better days. On the surface, the cottage was tidy upon arrival, but closer inspection revealed that it lacked a deep, thorough cleaning. While the main living areas were presentable, the corners, baseboards, and other area's not immediately...

Anonymous traveler

$395 nightly

Sep 22 - Sep 23

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

10. Charming Accommodations in the Hamptons

Sag Harbor

$469 nightly

Sep 22 - Sep 23

Total with taxes and fees

Iron/ironing board, WiFi (free), individually decorated

11. Windward Shores Ocean Resort

Napeague

Gaurang J

$143 nightly

Oct 12 - Oct 13

Total with taxes and fees

12. Black Swan Beachfront Home with Jacuzzi year round

Hampton Bays

Donald J.

$1,161 nightly

Sep 27 - Sep 28

Total with taxes and fees

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

Hampon Bays

Annie B.

$1,556 nightly

Sep 22 - Sep 23

Total with taxes and fees

14. North Fork Resort

Greenport

Harold

$270 nightly

Oct 19 - Oct 20

Total with taxes and fees

15. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

Napeague

Liana T.

$369 nightly

Sep 27 - Sep 28

Total with taxes and fees

Apartment | WiFi (free), individually decorated, individually furnished, bed sheets

16. Driftwood Resort

Montauk

William

$192 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

East Hampton

Christina V.

$260 nightly

Sep 24 - Sep 25

Total with taxes and fees

18. BlackBerry Private home with jacuzzi yearlong

East Hampton

Suzanne R.

$1,246 nightly

Sep 22 - Sep 23

Total with taxes and fees

19. Cliffside Resort Condominiums

Greenport

Christine

$372 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

Flanders

James W.

$285 nightly

Oct 6 - Oct 7

Total with taxes and fees

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Top Southampton Hotel Reviews

Harpoon House

10/10 Excellent

"Wonderful place great location I definitely recommend!"

Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa

10/10 Excellent

"We had a great stay at this house. This was our 3rd year doing this and by far the favorite house of my family. (3 adult kids plus sig others.) The deck and pool space were really comfortable and we used them a lot. The gym and sauna were huge bonuses that were also a big hit. I've actually rented in this area before and I really like the neighborhood. We would definitely consider renting this house next year, depending on our availability around this time of summer. Thanks to the owners for providing fun way to end the summer."

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

10/10 Excellent

"We did a large family trip to the Hamptons for Labor Day weekend 2026. It was a bucket list trip and the house well exceeded our expectations! It was plenty big and fit our group nicely. We also really enjoyed the location, the large yard and pool. It's a short walk to the water and a quick drive to get into Sag Harbor. The host was great and responded to all of our questions. The check-in, check-out process was also super easy. Highly recommend. We hope to book again in the coming years!"

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!⛱️

10/10 Excellent

"Pam was a wonderful host. It’s a beautiful property conveniently located in downtown Southampton. We’ve really enjoyed are stay and will surely be back in the near future."

Find out more about Southampton

Everything you need to know about Southampton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southampton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southampton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southampton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southampton. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southampton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $587 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southampton rentals

At Expedia, we put the best Southampton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southampton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southampton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southampton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Things to do in Southampton

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?

Private 2.1 acre gated home with heated pool and tennis & pickleball court: Visitors like this Southampton vacation home rental. It is located near the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and an arcade game room so you can immerse yourself in your vacation. Another good choice for your trip to Southampton is Minutes from the beach, brand new 4 bedroom.

How many vacation rentals are there in Southampton?

Expedia has 481 vacation rentals for your stay in Southampton.

What can I see and do in Southampton?

Enjoy the outdoors at Cooper's Beach and The Hamptons Beaches, or simply take in cultural attractions like Southampton Historical Museum and Shinnecock Nation Cultural Center and Museum. Other places in town to visit include Southampton Arts Center and Southampton Cultural Center.

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.

Southampton Vacation Rentals

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Check prices for these dates

Our top choices for Southampton vacation rentals

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

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

3. Minutes from the beach, brand new 3 bedroom

4. Minutes from the beach, brand new 4 bedroom

5. Newly Renovated Pristine Southampton Colonial

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

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

8. Safari Tent Glamping,S4-CedarPt, East Hampton, NY

9. Seabreeze #3 Cozy Cottage steps to the beach

10. Charming Accommodations in the Hamptons

11. Windward Shores Ocean Resort

12. Black Swan Beachfront Home with Jacuzzi year round

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

14. North Fork Resort

15. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

16. Driftwood Resort

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

18. BlackBerry Private home with jacuzzi yearlong

19. Cliffside Resort Condominiums

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

Find vacation rentals that suit your style

Top Southampton Hotel Reviews

Harpoon House

Find out more about Southampton

Explore a world of travel with Expedia

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