Southampton Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Southampton holiday rentals

Property grounds

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

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (15 reviews)
"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"
United States
Deborah V.
The price is HK$8,911
HK$12,396 total
includes taxes & fees
5 Feb - 6 Feb
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Interior

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

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.0 out of 10, Wonderful, (10 reviews)
"Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!"
United States
Panagiota K.
The price is HK$2,777
HK$6,581 total
includes taxes & fees
5 Feb - 6 Feb
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Smart TV, fireplace, stereo

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (3 reviews)
"perfect for families"
United States
Okito H.
The price is HK$3,515
HK$8,629 total
includes taxes & fees
5 Feb - 6 Feb
Minutes from the beach, brand new 4 bedroom
Exterior detail

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Calverton
8.6 out of 10, Excellent, (8 reviews)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is HK$2,285
HK$4,984 total
includes taxes & fees
12 Feb - 13 Feb
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Interior

Breakwater Estate… perfect for Large Group Getaways!

Breakwater Estate… perfect for Large Group Getaways!
Mattituck
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful property. Great pool, We had a great time."
United States
william p.
The price is HK$5,030
HK$10,793 total
includes taxes & fees
27 Feb - 28 Feb
Breakwater Estate… perfect for Large Group Getaways!
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is HK$851
HK$1,464 total
includes taxes & fees
5 Feb - 6 Feb
American Beech in Greenport - Petite King Room 7
Smart TV, fireplace

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (10 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
Renovated Townhouse walk to all
Terrace/patio

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (15 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is HK$773
HK$9,388 total
includes taxes & fees
10 Feb - 11 Feb
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Smart TV

Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is HK$430
HK$3,471 total
includes taxes & fees
9 Feb - 10 Feb
Seabreeze #3: Cozy Cottage by the beach
Outdoor dining

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Hampon Bays
9.6 out of 10, Exceptional, (23 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$586
HK$10,155 total
includes taxes & fees
5 Feb - 6 Feb
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
TV, fireplace, stereo, offices

East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
The price is HK$1,562
HK$5,703 total
includes taxes & fees
5 Feb - 6 Feb
East Hampton Estate for 8, Sauna, Soaking Tub, Chef`s Kitchen, Outdoor Fireplace
Dining

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is HK$2,144
HK$4,502 total
includes taxes & fees
5 Feb - 6 Feb
Northfork Townhouse walk to all
Interior

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (5 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is HK$9,373
HK$12,181 total
includes taxes & fees
5 Feb - 6 Feb
Cozy Hamptons Escape 3BR Minutes From Beach!
Beach

Seabreeze #4: Charming Cottage Footsteps to the Beach

Seabreeze #4: Charming Cottage Footsteps to the Beach
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is HK$586
HK$3,748 total
includes taxes & fees
18 Feb - 19 Feb
Seabreeze #4: Charming Cottage Footsteps to the Beach
Property grounds

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.6 out of 10, Exceptional, (10 reviews)
"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"
United States
Carine J.
Beachfront Greenport Villa
Fridge, microwave, oven, stovetop

Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is HK$773
HK$7,639 total
includes taxes & fees
9 Feb - 10 Feb
Blackberry: Private home with jacuzzi year-round
Smart TV, fireplace, ping pong, books

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Water Mill
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is HK$23,439
HK$45,873 total
includes taxes & fees
1 Mar - 2 Mar
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Dining

Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is HK$2,539
HK$4,908 total
includes taxes & fees
5 Feb - 6 Feb
Immaculate Waterfront 2 bedroom!
Interior

4-bedroom beach house minutes from Hamptons

4-bedroom beach house minutes from Hamptons
Calverton
10.0 out of 10, Exceptional, (1 review)
"Beautiful home and location. Owner was very helpful. Would love to rent again!"
United States
Evelyn D.
The price is HK$2,749
HK$5,523 total
includes taxes & fees
10 Feb - 11 Feb
4-bedroom beach house minutes from Hamptons
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

Southampton Inn

Southampton Inn

10/10 Excellent
"just a nice comfy feeling "
Gina 1-night trip
Posted 6 days ago
Southampton 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:

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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 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 Minutes from the beach, brand new 4 bedroom and Beautiful Southampton Village home, new reno, Heated pool!.

How many holiday rentals are there in Southampton?

Expedia has 514 holiday rentals for your stay in Southampton.

What can I see and do in Southampton?

Enjoy the outdoors at Cooper's Beach and Shinnecock East County Park, 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 North Main Street Historic District.

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.