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

Holiday Homes in Southampton

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Southampton holiday homes

A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

1. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
United States
Okito H.
The price is €1,381
includes taxes & fees
23 Sept - 24 Sept
Minutes from the beach, brand new 4 bedroom
A modern living room with a sofa, armchairs, a coffee table, and a TV.

2. 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 €1,223
includes taxes & fees
7 Sept - 8 Sept
Minutes from the beach, brand new 3 bedroom
A sandy beach with footprints leading to the water, a wooden bench, and a pair of shoes on the ground.

3. 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 €788
includes taxes & fees
20 Sept - 21 Sept
Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

4. 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 €1,070
includes taxes & fees
14 Sept - 15 Sept
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A wooden gate partially covered by lush green ivy.

5. 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, (16 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 €2,183
includes taxes & fees
8 Sept - 9 Sept
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
A modern kitchen with white cabinets, a stainless steel sink, and a dishwasher.

6. 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 €3,183
includes taxes & fees
8 Sept - 9 Sept
Newly Renovated Pristine Southampton Colonial
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

7. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is €523
includes taxes & fees
30 Sept - 1 Oct
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A wooden pathway leading to a beach with scattered rocks and greenery.

8. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is €351
includes taxes & fees
23 Sept - 24 Sept
Beach Block Hideaway
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

9. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (50 reviews)
"access"
United States
Timothy
The price is €317
includes taxes & fees
10 Sept - 11 Sept
The SandPiper
A covered patio area with a white sofa, wooden chairs, and a ceiling fan.

10. Villa Luz Family Home w/ heated pool & jacuzzi

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, Exceptional, (26 reviews)
"Everything was in order. When there were a couple of very minor glitches, the manager of the property was immediately responsive - and glitch gone, fast. This was one of the smoothest VRBO experiences we've had, and we've had many."
United States
Carola C.
The price is €1,807
includes taxes & fees
8 Sept - 9 Sept
Villa Luz Family Home w/ heated pool & jacuzzi
A beach with people relaxing, a pier extending into the water, and a clear sky.

11. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (29 reviews)
"We had a great stay!! "
United States
Callie E.
The price is €373
includes taxes & fees
8 Sept - 9 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

12. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (42 reviews)
"Such a wonderful stay! Christopher was such a great host, the property matched the description, was extremely clean and situated in a perfect location just a short walk from town! Would stay again & recommend to family/friends!"
United States
Anonymous traveller
The price is €340
includes taxes & fees
8 Sept - 9 Sept
Aqua Vista
A modern building with large windows overlooking a beach.

13. Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (18 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
United States
Donald J.
The price is €1,621
includes taxes & fees
8 Sept - 9 Sept
Black Swan Beachfront Home with Jacuzzi year round
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

14. 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 €808
includes taxes & fees
8 Sept - 9 Sept
Immaculate Waterfront 2 bedroom!
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

15. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is €1,066
includes taxes & fees
1 Sept - 2 Sept
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A spacious kitchen with white cabinets, a central island, and a dining area with a wooden table and chairs.

16. Luxury Sag Harbor Home with Heated Pool & Charm

Luxury Sag Harbor Home with Heated Pool & Charm
Sag Harbor
Luxury Sag Harbor Home with Heated Pool & Charm
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

17. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (43 reviews)
"My family and I really enjoyed this home. Everything you can think of is provided for you. We would definitely stay here again!"
United States
Sarah A.
The price is €837
includes taxes & fees
8 Sept - 9 Sept
Elegant 5-Bedroom Hamptons Home with Private Pool
A two-story building with a prominent sign reading 'Ivy Restaurant & Bar' on the front window.

18. Prime location, walk to all, cozy cottage Westhampton Beach

Prime location, walk to all, cozy cottage Westhampton Beach
Westhampton Beach
10.0 out of 10, Exceptional, (2 reviews)
"Adorable cottage in a perfect location to walk into West Hampton town and the beaches. Easy check-in with great communication. Plenty of amenities, including bikes, beach chairs, towels, and all you need to have a BBQ. Peaceful backyard - perfect to relax and read or enjoy an outside BBQ with family. I was with 2 girls friends and it was great for our needs."
United States
Cindy M.
The price is €501
includes taxes & fees
7 Sept - 8 Sept
Prime location, walk to all, cozy cottage Westhampton Beach
An outdoor dining area with hanging lights, palm trees, and a bar.

19. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is €384
includes taxes & fees
1 Sept - 2 Sept
American Beech in Greenport - Petite King Room 7
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

Private 2.1 acre gated home with heated pool and tennis & pickleball court

Private 2.1 acre gated home with heated pool and tennis & pickleball court

10/10 Excellent
"Nicely appointed house. The house was roomy and there were plenty of beds for everyone. Pool and tennis court was a great addition especially for the kids. Everyone had a wonderful time. The house could use a bigger water heater as we often ran out of hot water. Owner should have an exterminator to spray for ants in the kitchen."
Jill S. 7-night trip
Posted 2 days ago
Private 2.1 acre gated home with heated pool and tennis & pickleball court

Find out more about Southampton

Southampton Holiday Homes information

Number of reviews
253
Accommodation
194 Holiday Homes
Lowest Price
€317
Highest Price
€3,183