Southampton Holiday Rentals

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Holiday Rentals in Southampton

Pool
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
10.0 out of 10, Exceptional, (5)
"We loved our stay here! The hosts were very helpful and communicative leading up to and during our short stay. The house was perfect for our family - the pool area is fantastic and being able to grill food at the outdoor kitchen is such a bonus. No back and forth to the house for snacks or drinks! We spent the evening around the fire pit and the extended deck meant that there was plenty of room for us to relax and our kids to play. We also explored the local area and nearby beaches. The property...
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
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!
Outdoor dining
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (83)
"The house was so cute and a great location. Everything was easy to deal w and Pam was very flexible with timing. Will certainly hope to stay here again!"
The price is AU$1,988
per night
28 May - 29 May
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
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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
Fridge, microwave, oven, stovetop
Southampton Luxury. Walk to beach, kayaks on lake. Park-like grounds.
10.0 out of 10, Exceptional, (22)
"We had a last minute corporate retreat at this lovely Hamptons Home. In time to see the beautiful fall foliage starting, there is a nice partial view of the lake from the master bedroom balcony. Our large group was easily accommodated by the spacious rooms where each person had their own comfortable bed. The large living room with 4 couches made it easy to have our meetings in this open space. A few of us went to the beach, wine tasting and pumpkin picking all within a few minutes of the house...
Southampton Luxury. Walk to beach, kayaks on lake. Park-like grounds.
Property grounds
Newly Renovated Southampton Home with Heated Pool
Newly Renovated Southampton Home with Heated Pool
Property grounds
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
10.0 out of 10, Exceptional, (4)
The price is AU$5,247
per night
29 May - 30 May
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
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
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!
Private kitchen
Hamptons Style. Close to village restaurants, shops and ocean beach!
Hamptons Style. Close to village restaurants, shops and ocean beach!
Property grounds
Stellar Ocean Front Hamptons Getaway
Stellar Ocean Front Hamptons Getaway
A heated pool
Beautiful Southampton Home centrally located close to Sag Harbor,...
Beautiful Southampton Home centrally located close to Sag Harbor,...
A heated pool
Huge Backyard, Large Living Room with Dining Area, Large Den with Built-In...
10.0 out of 10, Exceptional, (11)
"We chose the property for the pool and hot tub in close proximity to family living in Southampton. It was the perfect size for our family of five. Having two living spaces (a living room plus a den) -- both with TVs was ideal. The beds were comfy, cozy and the house is well-appointed. We truly enjoyed the property and our stay. Two areas for consideration: the fireplace is wood burning and upon walking into the home we could smell burnt/stale air. The fireplace and/or flue may just need a...
Huge Backyard, Large Living Room with Dining Area, Large Den with Built-In...
Pool
Welcome to the J Luxury Southampton Estate w/Pool
9.8 out of 10, Exceptional, (27)
"Amazing weekend with a great house. We all loved our time there."
The price is AU$4,889
per night
16 June - 17 June
Welcome to the J Luxury Southampton Estate w/Pool
Property grounds
Tranquility at the Water’s Edge
10.0 out of 10, Exceptional, (2)
"Great stay. All essentials in place. Jeff made it easy."
Tranquility at the Water’s Edge
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
Property grounds
Recently constructed modern-style home with a private pool, open-floor...
Recently constructed modern-style home with a private pool, open-floor...
Property grounds
Southampton estate with saltwater pool, chefs kitchen, vast lawn,...
The price is AU$8,397
per night
22 May - 23 May
Southampton estate with saltwater pool, chefs kitchen, vast lawn,...
Fridge, microwave, oven, stovetop
Charming Southampton Village Home 4 Bedroom, 2 Bath 5 minutes from the beach
10.0 out of 10, Exceptional, (6)
"Deirdre was a wonderful host and extremely prompt in answering any questions we had. The house is exactly what we needed for our winter stay, a close drive to the beach and town center. We would recommend the hose and we would not hesitate to stay again."
Charming Southampton Village Home 4 Bedroom, 2 Bath 5 minutes from the beach
A heated pool
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
9.2 out of 10, Wonderful, (12)
"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...
Don't see what you're looking for?
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.

Southampton Holiday Home Travel Info

Number of holiday homes
99
Popular accommodation
Southampton private holiday homes
Known landmarks
Wolffer Estates Vineyard, Cooper's Beach and The Hamptons Beaches
International airports
New York, NY (JFK-John F. Kennedy Intl.), Newark, NJ (EWR-Liberty Intl.) and New York, NY (LGA-LaGuardia)

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, (72)
"Excellent rooms. Very spacious and comfortable. High-end modern furnishings. Highly recommended."
The price is AU$337
per night
27 May - 28 May
The Bentley Hotel Southampton
Outdoor pool
The Atlantic Hotel
2.5 star property
7.0 out of 10, Good, (768)
"Great prices, huge room, convenient and super friendly staff. Have stayed the past 3 weeks for business, good location"
The price is AU$292
per night
28 May - 29 May
The Atlantic Hotel
Traditional Single Room, 1 King Bed
Southampton Inn
3.0 star property
8.4 out of 10, Very good, (478)
"The accommodations and the amenities were very nice."
The price is AU$401
per night
27 May - 28 May
Southampton 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, 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 favourite 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 depend 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 AU$1,988 per night. Entering your travel dates in the search wizard might find you 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.

Recent reviews of Southampton properties
Expedia verified reviews

Capri

Capri

5/5 Excellent
"Loved it!"
A verified traveller stayed at Capri
Posted 2 days ago
Capri