Search Holiday Rentals in Southampton

April 2025

MondayTuesdayWednesdayThursdayFridaySaturdaySunday

May 2025

MondayTuesdayWednesdayThursdayFridaySaturdaySunday
  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Top Holiday Rentals in Southampton

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

10.0 out of 10, Exceptional, (19)
"Perfect spot for a girls weekend! Property/house as advertised, and the house was fully stocked with all amenities. Thanks for a wonderful stay!! "
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

10.0 out of 10, Exceptional, (98)
"Pam was very communicative prior to our stay and a welcoming host. The house was clean, centrally located, and spacious. "
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

Location and views! Located directly on Shinnecock Bay!

9.2 out of 10, Wonderful, (23)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
Location and views! Located directly on Shinnecock Bay!

Charming Village home in the heart of Southampton

10.0 out of 10, Exceptional, (20)
"We loved our stay! The location was perfect for our family, so easy to walk to town, close to the beach and easy to get to other towns. House was perfect as well, we didn’t get to enjoy the outdoors due to rain but loved the indoor space. Plenty of places to hang and enjoy/relax. Hoping to visit again soo!"
Charming Village home in the heart of Southampton

Sprawling Southampton Home: Private Pool

9.0 out of 10, Wonderful, (44)
"My family and I had a wonderful stay at this property. The house was well-situated in a quiet neighborhood - very private, surrounded by trees and a few wild turkeys. There were many amenities that made our stay enjoyable from the large patio and pool, 3 full baths in the main house, one of which had an amazing shower system with body spray, and a designated work area for those that can’t leave work behind. Communication with the property manager was easy and Debbie was very helpful and...
Sprawling Southampton Home: Private Pool

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

9.8 out of 10, Exceptional, (50)
"The house was perfect for a large group. Plenty of place to spread out and enjoy the space. The house was very spacious and had plenty of entertainment- the owner had everything you can imagine that you may need for a stay. The house is clean and in great shape. Such a great neighborhood to walk in and the beach is so nice and close by. Highly recommend for a fun Hamptons get away. The owner is very accommodating and flexible. He was accessible for restaurant/ activity recommendations. "
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

9.0 out of 10, Wonderful, (18)
"Very nice"
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

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

10.0 out of 10, Exceptional, (2)
Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families

Mary's Gated Oasis Private Estate

Mary's Gated Oasis Private Estate

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

9.6 out of 10, Exceptional, (15)
"The property was absolutely stunning! Very accommodating with many rooms for us all and the yard/ grounds were beautiful. Very modern and stylish interior yet cozy and inviting. Will definitely be keeping in mind for our next trip! "
Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa

Waterfront Sunset Views

10.0 out of 10, Exceptional, (20)
"We loved it so much we came back!! Always a pleasure to escape to this home. "
Waterfront Sunset Views

Minutes from the beach, brand new 4 bedroom

The price is £1,368
includes taxes & fees
6 Apr - 7 Apr
Minutes from the beach, brand new 4 bedroom

Contemporary Southampton Village Home Walking Distance to Town, Pool,...

10.0 out of 10, Exceptional, (11)
"My family of 6 and I stayed here for the Thanksgiving holiday. My 80 yr old parents live in Southampton but we decided to rent instead of burdening them w/guests. The house had a great layout on the first floor w/everything needed for the holiday, which was great. Walkable to town and Tate's Bake Shop, definitely a plus. Beautiful neighborhood. Some bumps, though: we struggled with getting into the house; no front door key given -- we accessed the home through a garage side-door electronic...
The price is £1,590
includes taxes & fees
4 May - 5 May
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Stunning Private Sunny Modern Southampton home-5 beds NEW WINTER HOT TUB for 7

9.8 out of 10, Exceptional, (19)
"Enjoyed our weekend stay at this beautiful home. It was everything that it stated and then some. We were in for a family weekend event and the homebase was perfect. Spacious and private at the same time. Back deck was perfect, pool was an added bonus! Perfect time had by all! thank you for the use of your beautiful home! "
Stunning Private Sunny Modern Southampton home-5 beds NEW WINTER HOT TUB for 7

Newly Renovated Southampton Home with Heated Pool

7.6 out of 10, Good, (4)
"Wonderful home. Perfect for family and entertaining. "
Newly Renovated Southampton Home with Heated Pool

Beautiful Southampton Home One Block from Shinnecock Bay, Town Shopping,...

9.4 out of 10, Exceptional, (3)
"We loved being together and the house and pool made it ideal for two weeks with an infant. We wished that there was better information/communication about lawn and pool service, pest treatment and trash pick-up. We were also bit disappointed that the outdoor table was not replace and we could not do any outdoor dinners."
Beautiful Southampton Home One Block from Shinnecock Bay, Town Shopping,...

Traditional Home w/ English Gardens, Pool, Rec Room, Close to Ocean Beaches

Traditional Home w/ English Gardens, Pool, Rec Room, Close to Ocean Beaches

Southampton Village Family Tradition Mint 5BR-5BR. Walkable location.

10.0 out of 10, Exceptional, (12)
"We had a wonderful stay at this beautiful home. Clean, beautifully decorated and all the amenities for a family vacation . The host was fabulous and shared recommendations for dinners and places to visit. We would definitely stay here again!"
Southampton Village Family Tradition Mint 5BR-5BR. Walkable location.

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

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 Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis

Beautiful Southampton Home with breathtaking waterfront views, front porch,...

9.6 out of 10, Exceptional, (4)
"We stayed for Labor Day weekend with my family, which were 6 adults (age from 20 to 76) and a teenager. Communication with stay marquis and especially the property owner was easy and quick. Every little detail was well thought out, owner was super responsive and helpful. House and property more beautiful than the photos and location is great, near beaches, downtown Southampton and nice restaurants. Can't say more how amazing the property is and again excellent interactions with the...
Beautiful Southampton Home with breathtaking waterfront views, front porch,...
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.
Don't see what you're looking for?
See all available properties in Southampton
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Southampton you may be interested in

The Atlantic Hotel

2.5 star property
7.0 out of 10, Good, (838)
"Great location, room layout was perfect, and easy check-in. "
The price is £150
includes taxes & fees
6 Apr - 7 Apr
The Atlantic Hotel

The Bentley Hotel Southampton

2.0 star property
9.4 out of 10, Exceptional, (235)
"So cute and roomy. Loved our stay. Will be back everytime we visit family up there. "
The price is £159
includes taxes & fees
14 Apr - 15 Apr
The Bentley Hotel Southampton

Southampton Inn

3.0 star property
8.6 out of 10, Excellent, (514)
"Nice place"
The price is £201
includes taxes & fees
4 Apr - 5 Apr
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.

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?

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖 : 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 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Some other top choices in Southampton are Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping and Sprawling Southampton Home: Private Pool.

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.