Southampton Vacation Rentals

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Vacation Rentals in Southampton

Vacation Home in Southampton

9.0 out of 10, Wonderful, (10)
"Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!"
United States
Panagiota K.
$718 nightly
The price is $820
Dec 6 - Dec 7
Total with taxes and fees
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Vacation Home in Southampton

10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
$971 nightly
The price is $1,109
Dec 7 - Dec 8
Total with taxes and fees
Minutes from the beach, brand new 4 bedroom

Vacation Home in Southampton

10.0 out of 10, Exceptional, (15)
"Just finished a 5 day stay. Best house rental ever! Great and thoughtful hosts. Super relaxing and extremely luxurious! Highly recommend!"
United States
William H.
$1,504 nightly
The price is $1,593
Jan 5 - Jan 6, 2026
Total with taxes and fees
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Vacation Home in Hampton Bays

9.6 out of 10, Exceptional, (13)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Vacation Home in Calverton

2.0 star property
$527 nightly
The price is $602
Dec 7 - Dec 8
Total with taxes and fees
4-bedroom beach house minutes from Hamptons

Cottage in Hampton Bays

8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
$398 nightly
The price is $455
Dec 10 - Dec 11
Total with taxes and fees
Seabreeze #4: Charming Cottage Footsteps to the Beach

Vacation Home in Calverton

2.0 star property
8.6 out of 10, Excellent, (8)
"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.
$582 nightly
The price is $665
Dec 6 - Dec 7
Total with taxes and fees
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Vacation Home in Water Mill

10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
$6,353 nightly
The price is $7,259
Dec 8 - Dec 9
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Apartment in Napeague

10.0 out of 10, Exceptional, (2)
"Loved having coffe on the deck enjoying the views. The location was perfect for us. Hope to be back!"
United States
Dianna L.
$692 nightly
The price is $775
Dec 8 - Dec 9
Total with taxes and fees
Unit 823 - Ocean Colony Beach and Tennis Club

Vacation Home in Greenport

9.0 out of 10, Wonderful, (4)
"Great job "
United States
emilio
$243 nightly
The price is $278
Dec 7 - Dec 8
Total with taxes and fees
American Beech in Greenport - Petite King Room 7

Vacation Home in East Hampton

9.0 out of 10, Wonderful, (4)
"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.
$771 nightly
The price is $881
Dec 15 - Dec 16
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round

Cottage in Greenport

10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
$457 nightly
The price is $522
Dec 8 - Dec 9
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Vacation Home in Hampon Bays

9.6 out of 10, Exceptional, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
$1,113 nightly
The price is $1,272
Jan 4 - Jan 5, 2026
Total with taxes and fees
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Vacation Home in East Hampton North

$760 nightly
The price is $810
Dec 7 - Dec 8
Total with taxes and fees
Designer East Hampton Farmhouse

Vacation Home in Hampton Bays

10.0 out of 10, Exceptional, (5)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
$549 nightly
The price is $627
Dec 7 - Dec 8
Total with taxes and fees
Immaculate Waterfront 2 bedroom!

Condo in Hampton Bays

4.0 star property
10.0 out of 10, Exceptional, (1)
$1,819 nightly
The price is $2,079
Dec 21 - Dec 22
Total with taxes and fees
Canoe Place Waterfront Residences

Cottage in Center Moriches

10.0 out of 10, Exceptional, (110)
"Amazing stay! Everything was super clean and beautiful "
United States
Liannys P.
$657 nightly
The price is $751
Dec 29 - Dec 30
Total with taxes and fees
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

Vacation Home in Sag Harbor

$5,630 nightly
The price is $6,432
Dec 10 - Dec 11
Total with taxes and fees
Spacious 5-bedroom house with water views and 2 houses from the bay.

Apartment in Napeague

10.0 out of 10, Exceptional, (1)
"Great spot! Nice to have beach access w/ chairs and umbrellas"
United States
Michael M.
$671 nightly
The price is $752
Dec 8 - Dec 9
Total with taxes and fees
Modern Studio Apt w/ Balcony & Pool View | 1 BTH

Vacation Home in Southold

10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveler
Beautifully farmhouse
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

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 $1,109 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.

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?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This highly rated vacation home rental in Southampton offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Southampton?

Expedia has 494 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 Shinnecock Nation Cultural Center and Museum. Other places in town to visit include Shinnecock Hills Golf Course and Southampton Arts 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.