Southampton Vacation Rentals from $555: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Southampton?

Private Bayfront Living, Water Views : Visitors like this Southampton vacation home rental. It is located on the beach and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a stovetop, a microwave, and a coffee maker, so you can cook with friends or family. Some other top choices in Southampton are Spacious Southampton Home in Shinnecock Hills, Central Between Southampton,... and Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping .

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Our top choices for Southampton vacation rentals

A covered patio with a table and chairs, large windows, and a view of greenery.

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

Southampton

Angelo D.

$486 nightly

Sep 27 - Sep 28

Total with taxes and fees

A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

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

Southampton

Justin

$797 nightly

Oct 21 - Oct 22

Total with taxes and fees

A modern living room with a sofa, armchairs, a coffee table, and a TV.

3. Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

$1,187 nightly

Sep 27 - Sep 28

Total with taxes and fees

A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

4. Minutes from the beach, brand new 4 bedroom

Southampton

Okito H.

$915 nightly

Oct 1 - Oct 2

Total with taxes and fees

A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

5. Amazing Southampton Home with Private Heated Pool

Southampton

Serina R.

$1,214 nightly

Sep 27 - Sep 28

Total with taxes and fees

A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

6. Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

$2,251 nightly

Sep 28 - Sep 29

Total with taxes and fees

A wooden gate partially covered by lush green ivy.

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

Southampton

Deborah V.

$3,123 nightly

Oct 4 - Oct 5

Total with taxes and fees

A wooden house with a front porch, white railings, and a double door.

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

Southampton

Melissa

$2,427 nightly

Oct 1 - Oct 2

Total with taxes and fees

A tented accommodation with two beds, a small table, a chair, and a cabinet.

9. Safari Tent Glamping,D27-CedarPt, East Hampton, NY

East Hampton

Brian

$257 nightly

Sep 27 - Sep 28

Total with taxes and fees

A spacious living room with a large sofa, a round coffee table, and a television. A kitchen with a refrigerator and cabinets is visible in the background.

10. Steps to the beach | Seabreeze Cottage #3

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

$438 nightly

Oct 4 - Oct 5

Total with taxes and fees

11. Windward Shores Ocean Resort

Napeague

Gaurang J

$143 nightly

Oct 12 - Oct 13

Total with taxes and fees

A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

12. Charming Accommodations in the Hamptons

Sag Harbor

$440 nightly

Sep 27 - Sep 28

Total with taxes and fees

A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

13. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

$1,496 nightly

Sep 27 - Sep 28

Total with taxes and fees

A modern building with large windows overlooking a beach.

14. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

Donald J.

$1,103 nightly

Oct 12 - Oct 13

Total with taxes and fees

A tent with a wooden frame, two red chairs, and a table.

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

East Hampton

Christina V.

$270 nightly

Oct 1 - Oct 2

Total with taxes and fees

16. Cliffside Resort Condominiums

Greenport

Christine

$333 nightly

Oct 25 - Oct 26

Total with taxes and fees

A modern house with a deck, outdoor seating, and a fire pit.

17. North Fork Resort

Greenport

Harold

$258 nightly

Oct 27 - Oct 28

Total with taxes and fees

18. Driftwood Resort

Montauk

William

$191 nightly

Oct 4 - Oct 5

Total with taxes and fees

A spacious living area with a large bed, a dining table, and a kitchen in the background.

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

Napeague

Liana T.

$351 nightly

Sep 27 - Sep 28

Total with taxes and fees

A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

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

Flanders

James W.

$264 nightly

Sep 29 - Sep 30

Total with taxes and fees

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Top Southampton Hotel Reviews

Harpoon House

10/10 Excellent

"Always stay here when I'm in town for clients during the summer 🤗"

Hamlet Inn

10/10 Excellent

"The hotel location is ideal. About a 2 mile radius from the town center, shopping, attractions and beaches. The room is very comfortable where all necessary amenity items are available. We had a nice closet in the room, a refrigerator and microwave. It would have been nice to have a couple of drawers if we had stayed more than 2 nights. The shower was particularly nice! Coffe, tea, soft drinks along with a wide variety of snacks, cakes and candy bars are available the entire day."

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

10/10 Excellent

"My wife and I were in town for a wedding. Michael was very nice and professional. Met us in the driveway and gave us the lay of the land. The unit was clean and had everything to you would need. Great location within walking distance of town. Would go back and stay again."

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."

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 $555 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 Bayfront Living, Water Views: Visitors like this Southampton vacation home rental. It is located on the beach and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a stovetop, a microwave, and a coffee maker, so you can cook with friends or family. Some other top choices in Southampton are Spacious Southampton Home in Shinnecock Hills, Central Between Southampton,... and Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping.

How many vacation rentals are there in Southampton?

Expedia has 483 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 Halsey House. 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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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. Amazing Southampton Home with Private Heated Pool

6. Newly Renovated Pristine Southampton Colonial

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

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

9. Safari Tent Glamping,D27-CedarPt, East Hampton, NY

10. Steps to the beach | Seabreeze Cottage #3

11. Windward Shores Ocean Resort

12. Charming Accommodations in the Hamptons

13. Jacuzzi year-round - Villa Luz Private Home

14. Beachfront Jacuzzi All Year - Black Swan Home

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

16. Cliffside Resort Condominiums

17. North Fork Resort

18. Driftwood Resort

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

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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