Holiday Rentals in Southampton

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Holiday 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, (82)
"Great property in a great location"
The price is €932
per night
3 May - 4 May
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
Property grounds
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
10.0 out of 10, Exceptional, (4)
The price is €3,735
per night
5 May - 6 May
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
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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
Tranquility at the Water’s Edge
10.0 out of 10, Exceptional, (1)
"The Host: From the beginning with booking to checking out of this property, Jeff has been a fabulous host. He provided quick responses and went above and beyond to answer all the questions I had. The House: Very clean and cozy. We spent a lot of time in the kitchen cooking and kids spent time in the eating area and the living room by the fire place. Although the weather wasn’t the best during our stay (windy and cold) when we had 1 nice day the kids had a blast clamming, kayaking and our...
Tranquility at the Water’s Edge
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 €2,589
per night
5 May - 6 May
Open Floor Plan, Spacious and Private Backyard with Patio and Pool, Close...
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
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, (26)
"The property was amazing! Owner was absolutely great communicating and providing us with everything we needed during our stay! Would definitely recommend this property for your next vacation spot!"
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
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
Pool
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
9.2 out of 10, Wonderful, (11)
"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...
Private kitchen
Hamptons Style. Close to village restaurants, shops and ocean beach!
Hamptons Style. Close to village restaurants, shops and ocean beach!
A heated pool
Beautiful Southampton Home centrally located close to Sag Harbor,...
Beautiful Southampton Home centrally located close to Sag Harbor,...
Property grounds
Southampton estate with saltwater pool, chefs kitchen, vast lawn,...
The price is €4,663
per night
5 May - 6 May
Southampton estate with saltwater pool, chefs kitchen, vast lawn,...
Exterior
coziest place to spend Thanksgiving, huge yard and proper dining room for family
coziest place to spend Thanksgiving, huge yard and proper dining room for family
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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.

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, (64)
"Recently renovated and clean but staff didn’t know what she was doing and couldn’t check us in until next shift covers came "
The price is €133
per night
6 May - 7 May
The Bentley Hotel Southampton
Traditional Single Room, 1 King Bed
Southampton Inn
3.0 star property
8.4 out of 10, Very good, (477)
"Wonderful Inn. Perfect stay. BUT I had a sort of remote room on the second floor with no elevator and as a lady of a certain age it was a struggle getting my suitcase up and down. NO ONE offered assistance or let me know in advance. Very inconsiderate. Abrupt woman at checkin and not a word of welcome. "
The price is €250
per night
5 May - 6 May
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, (348)
"It is quaint and i felt comfortable in the room"
The price is €132
per night
28 May - 29 May
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.

Everything you need to know about Southampton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southampton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Southampton holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southampton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southampton holiday rentals we have selected for you start as low as €932 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southampton rentals

At Expedia, we put the best Southampton holiday 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 holiday.

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 holiday rentals in Southampton?

Yes, there are holiday rentals close to the most popular sights in Southampton, 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 holiday rentals that Southampton has to offer?

Southampton Getaway with Hot Tub: This highly rated holiday home rental in Southampton offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub. Another good choice for your trip to Southampton is Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖 .

How many holiday rentals are there in Southampton?

Expedia has 473 holiday 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 holiday rentals like in Southampton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Southampton. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family trip.

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