Southampton Vacation Rentals

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Our top choices for Southampton vacation rentals

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"perfect for families"
United States
Okito H.
The price is ¥71,015
¥175,070 total
includes taxes & fees
May 16 - May 17
Minutes from the beach, brand new 4 bedroom

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Southampton
10.0 out of 10, Exceptional, (18 reviews)
"Great host & location. Would stay again"
United States
Chris H.
The price is ¥78,800
¥133,785 total
includes taxes & fees
Jun 2 - Jun 3
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
The price is ¥70,920
¥174,837 total
includes taxes & fees
May 15 - May 16
Minutes from the beach, brand new 3 bedroom

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 ¥283,288
¥396,837 total
includes taxes & fees
May 17 - May 18
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

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

Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
The price is ¥33,871
¥51,305 total
includes taxes & fees
May 21 - May 22
Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
The price is ¥33,871
¥53,284 total
includes taxes & fees
May 22 - May 23
Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
The price is ¥33,871
¥51,305 total
includes taxes & fees
May 25 - May 26
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (14 reviews)
"Great stay & great staff!"
United States
James
The price is ¥32,461
¥37,086 total
includes taxes & fees
May 20 - May 21
North Fork Cottages & RV Resort

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (312 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 ¥25,091
¥32,954 total
includes taxes & fees
May 17 - May 18
Windward Shores Ocean Resort

Seabreeze 4 Charming Cottage walk to US Open

Seabreeze 4 Charming Cottage walk to US Open
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is ¥32,938
¥97,685 total
includes taxes & fees
May 28 - May 29
Seabreeze 4 Charming Cottage walk to US Open

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (237 reviews)
"Wonderful location, right on the beach. The staff was kind and welcoming. The property was beautiful with a pool, playground, tennis and basketball courts, cornhole, etc. Very family friendly. Some walkable restaurants nearby and a quick 5-10 minute drive into town where a lot of the restaurants and shops are. We did have ants all in our food one day but the staff addressed it quickly "
United States
John
The price is ¥24,546
¥33,178 total
includes taxes & fees
May 19 - May 20
Driftwood Resort

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is ¥30,091
¥41,227 total
includes taxes & fees
Jun 7 - Jun 8
Cliffside Resort Condominiums

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is ¥33,871
¥50,944 total
includes taxes & fees
Jun 4 - Jun 5
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (16 reviews)
"The most amazing 24hrs! House is pristine, gorgeous view and very airy. Bedrooms each have their own bathroom and one more in the main living area. "
United States
Melissa M.
The price is ¥50,905
¥228,966 total
includes taxes & fees
May 26 - May 27
Black Swan Beachfront Home with Jacuzzi year round

Villa Luz Cozy Family Home with Jacuzzi year round

Villa Luz Cozy Family Home with Jacuzzi year round
Hampon Bays
9.6 out of 10, Exceptional, (24 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ¥50,747
¥306,306 total
includes taxes & fees
May 17 - May 18
Villa Luz Cozy Family Home with Jacuzzi year round

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (1 review)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is ¥29,944
¥59,781 total
includes taxes & fees
Jun 1 - Jun 2
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is ¥32,938
¥50,238 total
includes taxes & fees
May 21 - May 22
American Beech in Greenport - Petite King Room 7

Hamptons apartment getaway

Hamptons apartment getaway
East Quogue
6.0 out of 10, (3 reviews)
"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "
United States
Hilary K.
The price is ¥23,640
¥46,275 total
includes taxes & fees
May 15 - May 16
Hamptons apartment getaway

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
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 ¥50,973
¥202,220 total
includes taxes & fees
May 20 - May 21
BlackBerry Private home with jacuzzi yearlong
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

Find out more about Southampton

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Frequently asked questions

Can I find vacation rentals in Southampton?

Yes, you can find vacation 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 vacation rentals in Southampton?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: Visitors like this Southampton vacation home rental. It offers an outdoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Some other top choices in Southampton are Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️ and Charming Two-Story Retreat in Southampton Village walk to town, beach and train..

How many vacation rentals are there in Southampton?

Expedia has 547 vacation 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 vacation rentals like in Southampton?

Vacation rentals are private properties you can reserve for a short or long stay in Southampton. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.