Southampton Vacation Rentals

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Vacation Rentals in Southampton

Outdoor dining
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (83)
"The house was so cute and a great location. Everything was easy to deal w and Pam was very flexible with timing. Will certainly hope to stay here again!"
The price is CA $887
CA $1,326 total
includes taxes & fees
May 20 - May 21
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Fridge, microwave, oven, stovetop
Recently renovated private 2.1 acre gated home with heated pool and tennis court
10.0 out of 10, Exceptional, (11)
"This beautiful home was a great vacation home for our entire family! The house was impeccably clean with a ton of amenities, everything we wanted or needed was provided. The basketball/tennis court provided hours of entertainment for our family and the swimming pool made for a great leisurely morning or afternoon of swimming and relaxing poolside. Julie was a very attentive host and responded to our text messages for suggestions on Gurney's Seawater Spa, Vegan restaurants and more. We had a...
Recently renovated private 2.1 acre gated home with heated pool and tennis court
Fridge, microwave, oven, stovetop
Southampton Luxury. Walk to beach, kayaks on lake. Park-like grounds.
10.0 out of 10, Exceptional, (22)
"We had a last minute corporate retreat at this lovely Hamptons Home. In time to see the beautiful fall foliage starting, there is a nice partial view of the lake from the master bedroom balcony. Our large group was easily accommodated by the spacious rooms where each person had their own comfortable bed. The large living room with 4 couches made it easy to have our meetings in this open space. A few of us went to the beach, wine tasting and pumpkin picking all within a few minutes of the house...
Southampton Luxury. Walk to beach, kayaks on lake. Park-like grounds.
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Property grounds
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
10.0 out of 10, Exceptional, (4)
The price is CA $3,480
CA $4,193 total
includes taxes & fees
May 19 - May 20
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Terrace/patio
Huge Backyard, Large Living Room with Dining Area, Large Den with Built-In...
10.0 out of 10, Exceptional, (11)
"We chose the property for the pool and hot tub in close proximity to family living in Southampton. It was the perfect size for our family of five. Having two living spaces (a living room plus a den) -- both with TVs was ideal. The beds were comfy, cozy and the house is well-appointed. We truly enjoyed the property and our stay. Two areas for consideration: the fireplace is wood burning and upon walking into the home we could smell burnt/stale air. The fireplace and/or flue may just need a...
Huge Backyard, Large Living Room with Dining Area, Large Den with Built-In...
Fridge, microwave, oven, stovetop
Charming Southampton Village Home 4 Bedroom, 2 Bath 5 minutes from the beach
10.0 out of 10, Exceptional, (6)
"Deirdre was a wonderful host and extremely prompt in answering any questions we had. The house is exactly what we needed for our winter stay, a close drive to the beach and town center. We would recommend the hose and we would not hesitate to stay again."
Charming Southampton Village Home 4 Bedroom, 2 Bath 5 minutes from the beach
Fridge, microwave, oven, stovetop
Southampton Village Clean/Renovated Sun-filled Charming Home, Heated Salt Pool
10.0 out of 10, Exceptional, (50)
"We really enjoyed our time at Laura's house. The house was exactly as described, and Laura was so easy to communicate with. We loved the outdoor seating area / pool and that we could easily walk to downtown. Definitely hope to stay again."
Southampton Village Clean/Renovated Sun-filled Charming Home, Heated Salt Pool
A heated pool
Open Floor Plan, Spacious and Private Backyard with Patio and Pool, Close...
10.0 out of 10, Exceptional, (3)
The price is CA $2,714
CA $3,453 total
includes taxes & fees
May 19 - May 20
Open Floor Plan, Spacious and Private Backyard with Patio and Pool, Close...
Beach
Access to all the Hamptons has to offer
10.0 out of 10, Exceptional, (2)
"Charming house conveniently located between Sagg Harbor and Bridgehampton. Wonderful outdoor setting for dinners, lounging by the pool and enjoying the last weeks of summer. The pool and ping pong tables provided hours of fun on the occasional rainy day. Vincent was a wonderful host and was super organized and responsive. He thought of everything and made our experience a true pleasure."
Access to all the Hamptons has to offer
Property grounds
VILLAGE HOUSE RARE WATER VIEWS SO. OF HWY NEW PHOTOS
10.0 out of 10, Exceptional, (22)
"The house was perfect for our family. Ann was a great host. The house had everything you would ever need. We had a wonderful time!!!"
VILLAGE HOUSE RARE WATER VIEWS SO. OF HWY NEW PHOTOS
Property grounds
Tranquility at the Water’s Edge
10.0 out of 10, Exceptional, (2)
"Great stay. All essentials in place. Jeff made it easy."
Tranquility at the Water’s Edge
Outdoor pool, a heated pool
Beautiful Southampton Village/Fall Heated pool!
9.8 out of 10, Exceptional, (30)
"Absolutely stunning property, already planning a trip back! Owners are incredibly professional and communicative. House was clean and just as listed on VRBO. Thank you for sharing your amazing home with us!"
Beautiful Southampton Village/Fall Heated pool!
Pool
Welcome to the J Luxury Southampton Estate w/Pool
9.8 out of 10, Exceptional, (27)
"Amazing weekend with a great house. We all loved our time there."
Welcome to the J Luxury Southampton Estate w/Pool
Smart TV
Charming Village home in the heart of Southampton
9.8 out of 10, Exceptional, (10)
"Wonderful spot, simple and easy with a perfect neighborhood fir walking and direct access to town. Ideal"
Charming Village home in the heart of Southampton
Property grounds
Hamptons Retreat ☀️ 5 bed 4 bath, salt water pool, spa, walk to water 🏖sleep10
9.8 out of 10, Exceptional, (10)
"We had a lovely 3 days over Thanksgiving. Kirk could not be more attentive and gracious. Kitchen is well stocked. The sunroom was a nice cozy space for us to hang out. Thank you!"
Hamptons Retreat ☀️ 5 bed 4 bath, salt water pool, spa, walk to water 🏖sleep10
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (11)
"Since I stay for 2 days only it was fine. Check the shades , toilet paper and more towels. "
Location and views! Located directly on Shinnecock Bay!
Property grounds
Sprawling Southampton Home: Private Pool, Hot tub, Game Room
9.2 out of 10, Wonderful, (38)
"Great place to stay and hang with a group of close friends. Layout of rooms and open concept worked for our close group of 12. The pool room was a great space to hang after hours with music, pool, and ping pong. The location is close to the Southampton strip of boutiques and local pub as well as the North Fork wineries. Debbie, the property manager, was extremely responsive and the arrival/departure process was super smooth!"
Sprawling Southampton Home: Private Pool, Hot tub, Game Room
A heated pool
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
9.2 out of 10, Wonderful, (12)
"Where to even start. We have been using VRBO for a long time and this was by far the worst experience we have had. StayMarquis was absolutely terrible at managing expectations and any issues that arose. We checked-in on Sunday and the house was a mess. The trash was overflowing in the driveway, the pool and hot tub were gross, there were no cushions on the outdoor furniture (as shown in the pictures), the property did not seem like it was setup at all. Several issues were discovered the first...
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
Property grounds
Newly Renovated Southampton Home with Heated Pool
Newly Renovated Southampton Home with Heated Pool
Private kitchen
Hamptons Style. Close to village restaurants, shops and ocean beach!
Hamptons Style. Close to village restaurants, shops and ocean beach!
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See all available properties in Southampton
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.

Southampton Vacation Rental Travel Info

Other types of properties in Southampton you may be interested in

Terrace/patio
The Bentley Hotel Southampton
2.0 star property
9.2 out of 10, Wonderful, (69)
"We had a great stay"
The price is CA $214
CA $299 total
includes taxes & fees
May 16 - May 17
The Bentley Hotel Southampton
Traditional Single Room, 1 King Bed
Southampton Inn
3.0 star property
8.4 out of 10, Very good, (478)
"The accommodations and the amenities were very nice."
The price is CA $355
CA $428 total
includes taxes & fees
May 16 - May 17
Southampton Inn
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn
2.0 star property
8.4 out of 10, Very good, (353)
"The staff is very nice"
The price is CA $150
CA $194 total
includes taxes & fees
May 28 - May 29
Hamlet Inn
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.

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 close to top local attractions in Southampton, or you can select a more secluded option if you're looking for relaxation. Nature enthusiasts will enjoy the beaches in Southampton. Make sure you have time to check out the museums and festivals during your trip.

How many vacation rentals are there in Southampton?

Expedia has 473 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 Shinnecock Nation Cultural Center and Museum and Southampton Historical 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.

Recent reviews of Southampton properties
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