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

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Our top choices for Southampton vacation rentals

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

Southampton

Jordan

$514 nightly

Jul 26 - Jul 27

Total with taxes and fees

Beach nearby, sun loungers, beach towels

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

Southampton

Beverly J.

$1,084 nightly

Jul 26 - Jul 27

Total with taxes and fees

Minutes from the beach, brand new 3 bedroom

Southampton

Kathy B.

$1,485 nightly

Aug 2 - Aug 3

Total with taxes and fees

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

Southampton

Justin

$2,218 nightly

Jul 24 - Jul 25

Total with taxes and fees

Newly Renovated Pristine Southampton Colonial

Southampton

Brian M.

$3,330 nightly

Aug 2 - Aug 3

Total with taxes and fees

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

Southampton

Mergim S.

$4,537 nightly

Aug 1 - Aug 2

Total with taxes and fees

Amazing Southampton Home with Private Heated Pool

Southampton

$4,477 nightly

Aug 3 - Aug 4

Total with taxes and fees

Cliffside Resort Condominiums

Greenport

Suzanne

$501 nightly

Jul 21 - Jul 22

Total with taxes and fees

North Fork Resort

Greenport

James

$368 nightly

Jul 26 - Jul 27

Total with taxes and fees

Black Swan Beachfront Home with Jacuzzi year round

Hampton Bays

Ana B.

$1,831 nightly

Jul 21 - Jul 22

Total with taxes and fees

Seabreeze #3 Cozy Cottage steps to the beach

Hampton Bays

$552 nightly

Jul 21 - Jul 22

Total with taxes and fees

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

Windward Shores Ocean Resort

Napeague

Joseph

$506 nightly

Jul 23 - Jul 24

Total with taxes and fees

Hampton Bays Townhouse - Pool, Beach Access

Hampton Bays

Eileen O.

$590 nightly

Aug 14 - Aug 15

Total with taxes and fees

Lovely studio with AC in charming Sag Harbor

Sag Harbor

$594 nightly

Jul 21 - Jul 22

Total with taxes and fees

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

Driftwood Resort

Montauk

Rabia

$431 nightly

Jul 22 - Jul 23

Total with taxes and fees

Coffee/tea maker, fridge, microwave, stovetop

Hamptons Vacation Rental w/ Saltwater Pool

Hampton Bays

Cameron T.

$1,481 nightly

Aug 5 - Aug 6

Total with taxes and fees

Hamptons Tiana Bay Oasis

Hampton Bays

Anonymous traveler

$1,321 nightly

Aug 11 - Aug 12

Total with taxes and fees

Waterfront | Minutes to US Open| Private Water Access

Hampton Bays

Jamie M.

$1,563 nightly

Jul 22 - Jul 23

Total with taxes and fees

Villa Luz Family Home w/ heated pool & jacuzzi

Hampon Bays

Annie B.

$1,755 nightly

Jul 21 - Jul 22

Total with taxes and fees

Cozy Hamptons Escape 3BR Minutes From Beach!

Hampton Bays

Taylor H.

$1,366 nightly

Jul 21 - Jul 22

Total with taxes and fees

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Top Southampton Hotel Reviews

Hamlet Inn

10/10 Excellent

"I simply love the place! It’s quaint. It has all the amenities. Good beach access, just all the right stuff."

The Bentley Hotel Southampton

10/10 Excellent

"The staff at check in and check out were helpful and friendly. The suite was beautiful and felt like home. Also the entire room was extremely clean. The bed sheets were so soft! Most hotels they are like sand paper. Wish I traveled to this area more so I could stay there again. Wonderful experience."

Southampton Long Island Hotel

10/10 Excellent

"We had a great stay overall. Everything was very clean, and the staff was incredibly friendly and welcoming. The room was comfortable, and we really appreciated the excellent service. The only constructive feedback I’d like to share is about the toiletries. The soap and shampoo provided were very low quality and came in very small amounts. Unfortunately, they caused some skin irritation for me. Considering the price of the hotel, I think it would be worth investing in better-quality toiletries. There are many affordable options that would greatly improve the guest experience."

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

10/10 Excellent

"My friends and I stayed at Dave's for 4 nights over the 4th of July weekend and had the best time! The space was even better than advertised. The pool looked like a resort with enough chairs for all 8 of us and floats and there was an outdoor fridge to hold our beers. Dave was very communicative even when the power went out in the middle of the night and even offered to pay for our spoiled food. The house was very private and a great location close enough to get into town easily. The beds were comfortable and the water pressure/temp was perfect. Will definitely be booking with Dave again!"

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."

Peaceful and Private 4-Bedroom Home in Southampton

10/10 Excellent

"Excellent stay in Shinnecock Hills. The location is hard to beat — minutes from the golf course and well-positioned. The house is roomy and has all the amenities you'd want. The standout, though, is the backyard — generous, private, and a great spot to unwind. Clean, comfortable, and exactly as pictured. Would happily come back."

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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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?

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.: Visitors like this Southampton vacation home rental. It offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a dishwasher and a stovetop can make your vacation run smoothly. Some other top choices in Southampton are Peaceful and Private 4-Bedroom Home in Southampton and Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!⛱️.

How many vacation rentals are there in Southampton?

Expedia has 502 vacation rentals for your stay in Southampton.

What can I see and do in Southampton?

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

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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Upfront pricing

Check prices for these dates

Our top choices for Southampton vacation rentals

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

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

Minutes from the beach, brand new 3 bedroom

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

Newly Renovated Pristine Southampton Colonial

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

Amazing Southampton Home with Private Heated Pool

Cliffside Resort Condominiums

North Fork Resort

Black Swan Beachfront Home with Jacuzzi year round

Seabreeze #3 Cozy Cottage steps to the beach

Windward Shores Ocean Resort

Hampton Bays Townhouse - Pool, Beach Access

Lovely studio with AC in charming Sag Harbor

Driftwood Resort

Hamptons Vacation Rental w/ Saltwater Pool

Hamptons Tiana Bay Oasis

Waterfront | Minutes to US Open| Private Water Access

Villa Luz Family Home w/ heated pool & jacuzzi

Cozy Hamptons Escape 3BR Minutes From Beach!

Find vacation rentals that suit your style

Top Southampton Hotel Reviews

Hamlet Inn

Find out more about Southampton

Explore a world of travel with Expedia

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