A beach with a wooden fence, a lifeguard tower, and a house with a balcony overlooking the ocean.

Southampton Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Southampton holiday rentals

Outdoor dining

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Southampton
9.6 out of 10, Exceptional, (7 reviews)
"great experience"
United States
Jordan
The price is HK$2,744
HK$4,604 total
includes taxes & fees
20 Jul - 21 Jul
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Beach nearby, sun-loungers, beach towels

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Southampton
10.0 out of 10, Exceptional, (2 reviews)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
United States
Beverly J.
The price is HK$5,331
HK$10,032 total
includes taxes & fees
9 Aug - 10 Aug
Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Living area

Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"Great location. Loved the yard but for small pets the fence has some areas they could get under but overall it worked out. Just kept an eye on them.House very clean, comfortable. Host communication was excellent and would highly recommend for a visit to Southampton. Easy walk into town."
United States
Kathy B.
The price is HK$7,056
HK$13,230 total
includes taxes & fees
2 Aug - 3 Aug
Minutes from the beach, brand new 3 bedroom
Interior

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is HK$14,387
HK$21,739 total
includes taxes & fees
24 Jul - 25 Jul
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Interior

Newly Renovated Pristine Southampton Colonial

Newly Renovated Pristine Southampton Colonial
Southampton
9.8 out of 10, Exceptional, (12 reviews)
"Great property, worked perfectly for my crew that was in town for an event. Great communication with Brian the owner and very easy stay. Would stay again!"
United States
Brian M.
The price is HK$20,992
HK$30,119 total
includes taxes & fees
31 Jul - 1 Aug
Newly Renovated Pristine Southampton Colonial
Exterior detail

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

COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
Southampton
9.2 out of 10, Wonderful, (28 reviews)
"House was incredible shape, lots of amenities and space for any kind of stay you wish to have. Daniel from the StayMarquis team was very communicative throughout the trip, and every detail was accounted for!"
United States
Mergim S.
The price is HK$29,671
HK$40,233 total
includes taxes & fees
1 Aug - 2 Aug
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
Outdoor pool, a heated pool

Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
The price is HK$27,683
HK$39,994 total
includes taxes & fees
3 Aug - 4 Aug
Amazing Southampton Home with Private Heated Pool
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (272 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
United States
Suzanne
The price is HK$2,443
HK$3,131 total
includes taxes & fees
23 Jul - 24 Jul
Cliffside Resort Condominiums
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (32 reviews)
"Great stay & great staff!"
United States
James
The price is HK$4,142
HK$4,732 total
includes taxes & fees
2 Aug - 3 Aug
North Fork Resort
Terrace/patio

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (17 reviews)
"Amazing views, beautiful property and pet friendly! Clean, well equipped."
United States
Ana B.
The price is HK$5,825
HK$15,618 total
includes taxes & fees
21 Jul - 22 Jul
Black Swan Beachfront Home with Jacuzzi year round
Smart TV, offices

Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,497
HK$4,684 total
includes taxes & fees
20 Jul - 21 Jul
Seabreeze #3 Cozy Cottage steps to the beach
Iron/ironing board, free WiFi, individually decorated

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (319 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is HK$3,400
HK$4,098 total
includes taxes & fees
20 Jul - 21 Jul
Windward Shores Ocean Resort
Outdoor dining

Hampton Bays Townhouse - Pool, Beach Access

Hampton Bays Townhouse - Pool, Beach Access
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
"This was the perfect spot for us for a quick weekend stay in Hampton Bays. Close to Ponquoge Beach, restaurants, stores, etc. Great size for our group of four. We didn’t get a chance to use the pool because we didn’t get the good weather, but we will be back. Good value for price. Irina was excellent at communicating. We loved our short stay here. Would highly recommend to my friends."
United States
Eileen O.
The price is HK$2,470
HK$5,060 total
includes taxes & fees
14 Aug - 15 Aug
Hampton Bays Townhouse - Pool, Beach Access
Exterior

Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
The price is HK$2,705
HK$5,321 total
includes taxes & fees
20 Jul - 21 Jul
Lovely studio with AC in charming Sag Harbor
Free WiFi, individually decorated, individually furnished, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (242 reviews)
"Very close to beach"
United States
Rabia
The price is HK$4,384
HK$5,264 total
includes taxes & fees
2 Aug - 3 Aug
Driftwood Resort
Coffee/tea maker, fridge, microwave, stovetop

Hamptons Vacation Rental w/ Saltwater Pool

Hamptons Vacation Rental w/ Saltwater Pool
Hampton Bays
9.8 out of 10, Exceptional, (7 reviews)
"Had a great stay."
United States
Cameron T.
The price is HK$7,628
HK$13,213 total
includes taxes & fees
5 Aug - 6 Aug
Hamptons Vacation Rental w/ Saltwater Pool
Outdoor pool, a heated pool

Hamptons Tiana Bay Oasis

Hamptons Tiana Bay Oasis
Hampton Bays
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed this newly renovated home and had a wonderful time. Beautiful pool and grounds. "
United States
Anonymous traveller
The price is HK$6,896
HK$11,775 total
includes taxes & fees
27 Jul - 28 Jul
Hamptons Tiana Bay Oasis
Outdoor dining

Waterfront | Minutes to US Open| Private Water Access

Waterfront | Minutes to US Open| Private Water Access
Hampton Bays
10.0 out of 10, Exceptional, (6 reviews)
"We had the best time here! Carrie was so helpful and wonderful to communicate with. We were right on the water and could not get enough of the view!"
United States
Jamie M.
The price is HK$7,689
HK$12,126 total
includes taxes & fees
21 Jul - 22 Jul
Waterfront | Minutes to US Open| Private Water Access
Outdoor dining

Villa Luz Family Home w/ heated pool & jacuzzi

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, Exceptional, (25 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is HK$2,164
HK$14,788 total
includes taxes & fees
21 Jul - 22 Jul
Villa Luz Family Home w/ heated pool & jacuzzi
Interior

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.0 out of 10, Wonderful, (6 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is HK$9,408
HK$12,281 total
includes taxes & fees
20 Jul - 21 Jul
Cozy Hamptons Escape 3BR Minutes From Beach!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southampton Hotel Reviews

Hamlet Inn

Hamlet Inn

10/10 Excellent
"I simply love the place! It’s quaint. It has all the amenities. Good beach access, just all the right stuff."
Sharon 1-night trip
Posted 8 hours ago
Hamlet Inn

Find out more about Southampton

Search for holiday rentals in Southampton on Expedia! You can easily find your home rentals, villas, holiday apartments in Southampton using one of the methods below:

  • View our selection of featured holiday rentals in Southampton
  • Use the map to find apartments and other holiday homes in the Southampton neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southampton while they last

Look no further and take a look at our great range of rental properties in Southampton!

Frequently asked questions

Can I find holiday rentals in Southampton?

Yes, there are holiday rentals in Southampton close to Southampton Arts Center, 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?

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.: This highly rated holiday home rental in Southampton offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a stovetop can make your holiday run smoothly. Some other top choices in Southampton are Peaceful and Private 4-Bedroom Home in Southampton and Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!⛱️.

How many holiday rentals are there in Southampton?

Expedia has 502 holiday rentals for your stay in Southampton.

What can I see and do in Southampton?

Enjoy the outdoors at The Hamptons Beaches and Cooper's Beach, 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 Shinnecock Hills Golf Course.

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.