Holiday Rentals in Southampton

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Holiday Rentals in Southampton

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

9.8 out of 10, Exceptional, (53)
"Our family (16) spent a week at the property and found the house and property in good order, comfortable and convenient to the bay and other attractions. I would definitely recommend it as a great family vacation."
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (29)
"Amazing property! Had all the things we needed "
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Location and views! Located directly on Shinnecock Bay!

9.2 out of 10, Wonderful, (29)
"Cute beach bungalow vibe. The outdoor space, grill, and firepit made this property worthwhile! Lori's a wonderful, accomodating host."
Location and views! Located directly on Shinnecock Bay!

Stunning Southampton Village Modern Home

The price is €14,925
includes taxes & fees
4 Sept - 5 Sept
Stunning Southampton Village Modern Home

Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families

9.4 out of 10, Exceptional, (6)
"Loved it! "
Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

10.0 out of 10, Exceptional, (13)
"Great property for two people right next to the downtown. Our stay was comfortable and clean!"
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Newly Renovated Pristine Southampton Colonial

9.8 out of 10, Exceptional, (12)
"This property worked great for us. Close to everywhere we need to be. Very clean as well."
Newly Renovated Pristine Southampton Colonial

Resort Style backyard including professional PICKLEBALL COURT and HOT TUB.

9.8 out of 10, Exceptional, (63)
"House was very clean! Owner was attentive. Highly recommend for a family vacation! Kids were never bored! "
Resort Style backyard including professional PICKLEBALL COURT and HOT TUB.

Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts

9.8 out of 10, Exceptional, (19)
"House was perfectly appointed in Southampton! Close to all the spots--Southampton town, Bridgehampton shopping and quaint Sag Harbor"
Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts

Minutes from the beach, brand new 4 bedroom

10.0 out of 10, Exceptional, (1)
"Great property for a family trip out to Southampton. Clean and well appointed home. Easy check in and host was very accommodating. Close to everything. Would definitely stay here again. "
The price is €1,552
includes taxes & fees
1 Sept - 2 Sept
Minutes from the beach, brand new 4 bedroom

Spacious Southampton Home in Shinnecock Hills, Central Between Southampton,...

10.0 out of 10, Exceptional, (4)
"Great time! Great house! Thank you"
Spacious Southampton Home in Shinnecock Hills, Central Between Southampton,...

Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa

9.8 out of 10, Exceptional, (18)
"We had a wonderful time in the Hamptons. The house was beautiful!"
Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa

Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

9.8 out of 10, Exceptional, (25)
"Ken was great and easy to work with. The house was nice and perfect for our stay!"
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

Southampton Home with Heated Pool,6 minutes from beach’s

7.6 out of 10, Good, (4)
"Good location close to everything "
Southampton Home with Heated Pool,6 minutes from beach’s

2-bedroom apartment in beautiful Southampton with a beach permit

"Very nice stay in this newly renovated apartment. Great location for town. "
2-bedroom apartment in beautiful Southampton with a beach permit

Southampton - Walk to water/10 min drive to area beaches and Southampton Village

10.0 out of 10, Exceptional, (2)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
Southampton - Walk to water/10 min drive to area beaches and Southampton Village

Southampton Village Oasis Summer 2025 S/O, Thinking September in Hamptons?

10.0 out of 10, Exceptional, (20)
"Gregg and Danielle have themselves a gem in the hamptons. Beautiful property, beautiful pool area, beautiful house. "
Southampton Village Oasis Summer 2025 S/O, Thinking September in Hamptons?

Hamptons Modern Retreat NEW CONS

10.0 out of 10, Exceptional, (12)
"Property was was everything and more than described!"
Hamptons Modern Retreat NEW CONS

New Construction Modern Luxury Retreat w 6 Beds

10.0 out of 10, Exceptional, (6)
"The house was as advertised. Immaculate condition and easy access to everywhere in Southampton. The pool was amazing and any issues were addressed promptly. I would definitely recommend this house."
New Construction Modern Luxury Retreat w 6 Beds

Stunning House: Tennis & Pool in Southampton Estate section

10.0 out of 10, Exceptional, (38)
"Wonderful place , great time and memories, Owners were very gracious and helpful"
Stunning House: Tennis & Pool in Southampton Estate section
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

Find out more about Southampton

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 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?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This highly rated holiday home rental in Southampton offers an outdoor pool, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Some other top choices in Southampton are Charming Village home in the heart of Southampton and Charming Two-Story Retreat in Southampton Village walk to town, beach and train..

How many holiday rentals are there in Southampton?

Expedia has 470 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.