Southampton Vacation Rentals

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Our top choices for Southampton vacation rentals

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

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.0 out of 10, Wonderful, (10 reviews)
"Great location. Great host. Easy house, pool and private back yard. It's modest but has it all."
United States
Harry V.
The price is CA $360
CA $983 total
includes taxes & fees
Feb 13 - Feb 14
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (3 reviews)
"perfect for families"
United States
Okito H.
The price is CA $610
CA $1,504 total
includes taxes & fees
Feb 15 - Feb 16
Minutes from the beach, brand new 4 bedroom

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (305 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is CA $179
CA $234 total
includes taxes & fees
Feb 12 - Feb 13
Windward Shores Ocean Resort

Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool

Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
East Hampton North
The price is CA $150
CA $891 total
includes taxes & fees
Feb 13 - Feb 14
Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (15 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is CA $134
CA $1,635 total
includes taxes & fees
Feb 12 - Feb 13
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is CA $75
CA $617 total
includes taxes & fees
Feb 12 - Feb 13
Seabreeze #3: Cozy Cottage by the beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Water Mill
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is CA $4,066
CA $7,836 total
includes taxes & fees
Mar 1 - Mar 2
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is CA $161
CA $273 total
includes taxes & fees
Feb 18 - Feb 19
American Beech in Greenport - Petite King Room 7

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Hampon Bays
9.6 out of 10, Exceptional, (23 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is CA $134
CA $1,809 total
includes taxes & fees
Feb 18 - Feb 19
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
The price is CA $150
CA $842 total
includes taxes & fees
Feb 13 - Feb 14
East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace

Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is CA $134
CA $1,326 total
includes taxes & fees
Feb 18 - Feb 19
Blackberry: Private home with jacuzzi year-round

Seabreeze #4: Charming Cottage Footsteps to the Beach

Seabreeze #4: Charming Cottage Footsteps to the Beach
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is CA $102
CA $652 total
includes taxes & fees
Feb 18 - Feb 19
Seabreeze #4: Charming Cottage Footsteps to the Beach

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
The price is CA $5,422
CA $8,661 total
includes taxes & fees
Feb 18 - Feb 19
Spacious 5-bedroom house with water views and 2 houses from the bay.

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is CA $380
CA $806 total
includes taxes & fees
Feb 17 - Feb 18
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

5 Bedrooms! 4 Min to the Beach! HEATED POOL!

5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Westhampton Beach
10.0 out of 10, Exceptional, (2 reviews)
"awesome house and awesome host"
United States
Matthew M.
The price is CA $1,947
CA $2,962 total
includes taxes & fees
Feb 16 - Feb 17
5 Bedrooms! 4 Min to the Beach! HEATED POOL!

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is CA $2,025
CA $2,636 total
includes taxes & fees
Feb 12 - Feb 13
Cozy 5 Bedroom With Wi-fi And Air Condition

Cottage on Beach front Estate with Dockage .Walk to Village

Cottage on Beach front Estate with Dockage .Walk to Village
Pipes Cove
10.0 out of 10, Exceptional, (75 reviews)
"Wonderful stay at such a special spot. "
United States
Meg B.
The price is CA $407
CA $531 total
includes taxes & fees
Feb 28 - Mar 1
Cottage on Beach front Estate with Dockage .Walk to Village

4-bedroom beach house minutes from Hamptons

4-bedroom beach house minutes from Hamptons
Calverton
10.0 out of 10, Exceptional, (1 review)
"Beautiful home and location. Owner was very helpful. Would love to rent again!"
United States
Evelyn D.
The price is CA $464
CA $951 total
includes taxes & fees
Feb 23 - Feb 24
4-bedroom beach house minutes from Hamptons

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Calverton
8.6 out of 10, Excellent, (8 reviews)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is CA $396
CA $868 total
includes taxes & fees
Feb 13 - Feb 14
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
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.
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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 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.

What are some of the best vacation rentals in Southampton?

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️: 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 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other top choices in Southampton are Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping and Hamptons Modern Retreat NEW CONS.

How many vacation rentals are there in Southampton?

Expedia has 513 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 Southampton Historical Museum and Shinnecock Nation Cultural Center and 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.