Southampton Holiday Rentals

Holiday Rentals in Southampton

Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (12)
"You have the opportunity to attend a graduation party at the Hamptons, where everyone had to find their own accommodations. The location is essentially located to town to the water and beautiful scenic paths. The host insured that the home was exceptionally clean and amenities provided. Not to mention accommodating due to last-minute change in schedule."
Location and views! Located directly on Shinnecock Bay!
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
Beautiful 2bedroom w Pool close to the beach and Southampton Village
9.6 out of 10, Exceptional, (4)
"We had a wonderful stay at this property. The apartment was spacious and very clean. The outdoor area was perfect, the kids enjoyed the pool and swing/slide set. Would definitely recommend!"
Beautiful 2bedroom w Pool close to the beach and Southampton Village
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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 NZ$1,586
per night
26 Jun - 27 Jun
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
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.
Outdoor pool, a heated pool
Beautiful Southampton Village/Fall Heated pool!
10.0 out of 10, Exceptional, (31)
"!!"
Beautiful Southampton Village/Fall Heated pool!
A heated pool
Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa
10.0 out of 10, Exceptional, (11)
Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa
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 NZ$5,667
per night
28 May - 29 May
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Smart TV, fireplace, ping pong, stereo
Recently constructed modern-style home with a private pool, open-floor...
Recently constructed modern-style home with a private pool, open-floor...
Property grounds
Sprawling Southampton Home: Private Pool, 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, Game Room
Property grounds
5BR, Luxury Home, Pool, Large Yard , Close to Beach & Town
9.6 out of 10, Exceptional, (7)
"My family and I recently stayed at this home for a week in the Hamptons and had a wonderful time. The home was clean and pretty much had everything we needed. The owners were very accessible and eager to answer any of our questions/concerns. My children loved the pool and the basketball hoop in the driveway. It truly felt like our home away from home! I highly recommend staying here."
5BR, Luxury Home, Pool, Large Yard , Close to Beach & Town
Outdoor pool, a heated pool
Escape to the Hamptons! Chic Beach Home mins from Village
10.0 out of 10, Exceptional, (7)
"We've been renting a lot - specifically through VRBO - across multiple countries. VRBO has been great. This house is great as well. - Very good communications from owner. Short, to the point, timely! "Timely" is important! - Check-in procedure is as easy as it can possible be. - The locations works - 8 min driving from the village and the beach. - Clean, bright, well-appointed house. The guest house was remodeled and feels great."
Escape to the Hamptons! Chic Beach Home mins from Village
Private kitchen
Hamptons Style. Close to village restaurants, shops and ocean beach!
Hamptons Style. Close to village restaurants, shops and ocean beach!
Smart TV, fireplace, ping pong, books
Newly Renovated Southampton Getaway House
10.0 out of 10, Exceptional, (3)
"This house is amazing. The space was perfect for a family week. Great open kitchen and hang out space including plenty of games and activities. The property is lovely with a great pool and plenty of space. We loved it and would easily return."
Newly Renovated Southampton Getaway House
Property grounds
Stellar Ocean Front Hamptons Getaway
Stellar Ocean Front Hamptons Getaway
Microwave, oven, stovetop, coffee/tea maker
Spacious Southampton Home in Shinnecock Hills, Central Between Southampton,...
Spacious Southampton Home in Shinnecock Hills, Central Between Southampton,...
A heated pool
Contemporary Residence on .43 Acres, Spacious Indoor and Outdoor Living...
10.0 out of 10, Exceptional, (3)
"Overall Impressuon property was clean and beautiful...no complaints"
Contemporary Residence on .43 Acres, Spacious Indoor and Outdoor Living...
A heated pool
Beautiful Southampton Home centrally located close to Sag Harbor,...
Beautiful Southampton Home centrally located close to Sag Harbor,...
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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
9.4 out of 10, Exceptional, (74)
"Spacious and clean with wonderful staff. "
The price is NZ$368
per night
2 Jun - 3 Jun
The Bentley Hotel Southampton
Outdoor pool
The Atlantic Hotel
2.5 star property
7.0 out of 10, Good, (771)
"Great prices, huge room, convenient and super friendly staff. Have stayed the past 3 weeks for business, good location"
The price is NZ$322
per night
30 May - 31 May
The Atlantic Hotel
Traditional Single Room, 1 King Bed
Southampton Inn
3.0 star property
8.4 out of 10, Very good, (481)
"great location "
The price is NZ$541
per night
30 May - 31 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Southampton holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Southampton. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Southampton. Seeing all the best attractions is bound to make you fall in love with Southampton. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Southampton short-term rentals, that won’t be hard to do.

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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