Southampton Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Southampton vacation rentals

Interior

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 ￥41,022
￥112,007 total
includes taxes & fees
Feb 13 - Feb 14
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Smart TV, fireplace, stereo

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 ￥69,530
￥171,409 total
includes taxes & fees
Feb 15 - Feb 16
Minutes from the beach, brand new 4 bedroom
Individually decorated, individually furnished, iron/ironing board

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 ￥20,191
￥26,402 total
includes taxes & fees
Feb 17 - Feb 18
Windward Shores Ocean Resort
Dining

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 ￥17,151
￥101,620 total
includes taxes & fees
Feb 13 - Feb 14
Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
Terrace/patio

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 ￥19,314
￥191,534 total
includes taxes & fees
Feb 24 - Feb 25
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Smart TV

Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
Seabreeze #3: Cozy Cottage by the beach
Smart TV, fireplace, table tennis, books

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 ￥463,530
￥907,179 total
includes taxes & fees
Mar 1 - Mar 2
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Terrace/patio

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 ￥18,387
￥31,069 total
includes taxes & fees
Feb 17 - Feb 18
American Beech in Greenport - Petite King Room 7
Terrace/patio

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 ￥15,296
￥206,538 total
includes taxes & fees
Feb 17 - Feb 18
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
TV, fireplace, stereo, offices

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 ￥17,151
￥96,022 total
includes taxes & fees
Feb 13 - Feb 14
East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace
Fridge, microwave, oven, stovetop

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 ￥15,296
￥148,992 total
includes taxes & fees
Feb 17 - Feb 18
Blackberry: Private home with jacuzzi year-round
Beach

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 ￥11,588
￥74,319 total
includes taxes & fees
Feb 17 - Feb 18
Seabreeze #4: Charming Cottage Footsteps to the Beach
Smart TV, fireplace

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 ￥618,040
￥978,141 total
includes taxes & fees
Feb 16 - Feb 17
Spacious 5-bedroom house with water views and 2 houses from the bay.
Smart TV, books

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 ￥44,035
￥91,797 total
includes taxes & fees
Feb 19 - Feb 20
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Smart TV, fireplace, computer monitors, printers

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 ￥244,418
￥368,011 total
includes taxes & fees
Feb 25 - Feb 26
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Living area

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is ￥228,941
￥298,682 total
includes taxes & fees
Feb 20 - Feb 21
Cozy 5 Bedroom With Wi-fi And Air Condition
Terrace/patio

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 ￥46,353
￥59,667 total
includes taxes & fees
Feb 28 - Mar 1
Cottage on Beach front Estate with Dockage .Walk to Village
Interior

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 ￥52,842
￥108,388 total
includes taxes & fees
Feb 23 - Feb 24
4-bedroom beach house minutes from Hamptons
Exterior detail

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 ￥45,194
￥99,297 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

Southampton Long Island Hotel

Southampton Long Island Hotel

10/10 Excellent
"I had to stay one night only, for a short business trip and I am glad i found this place. I was not expecting the most luxury nor up to date hotel after reading some reviews but as long as it was clean i was satisfied. Well, i booked the small room and i was very pleased, it was immaculately clean, the sheets were super soft, and all pressed. This will be my regular place every time I need to travel to this area. I am.glad I found it and i didn't break the bank to stay in The Hamptons. "
ANDREA 1-night trip
Posted 7 days ago
Southampton Long Island Hotel

Find out more about Southampton

Search for holiday rentals in Southampton on Expedia! You can easily find your home rentals, villas, holiday apartments in Southampton using one of the methods below:

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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.