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Compare 1490 Vacation Homes in Southold with updated reviews, rates, and availability.

Gorgeous private Hamptons house with pool and volleyball court
8.4 out of 10, Very Good, (17)
"We had a great stay at the house. However, there were a few things that definitely needed improvements. The pool deck is old and had a many places where the boards were sunk in and in need of replacement which made it hard to walk around safely. Also, when we arrived there was only one roll of toilet paper in each bathroom and not enough hand soap in each bathroom so we had to go out and purchase our own. Other than that, the place was clean and we enjoyed the open space in the home. We would...
Gorgeous private Hamptons house with pool and volleyball court
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
10.0 out of 10, Exceptional, (15)
"Our group of friends stayed at this house for a long weekend in October 2024. The house is just as good or better than the pictures in the listing. Very clean and updated inside and out. Most importantly, the bathrooms and kitchen are clean and updated. And the huge backyard with pool, hot tub, and outdoor shower takes this house to the next level. The backyard space is great for families, small groups, or anyone looking for a quiet private space to relax. The owner/manager was very...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, (163)
"We had an amazing stay at this Vrbo property! The home was incredibly clean and spacious, offering more than enough room for everyone to feel comfortable. It was beautifully furnished, making our stay both luxurious and cozy. The location couldn’t have been more perfect, close to everything we needed yet in a peaceful neighborhood. Communication with the host was seamless—quick responses and very accommodating to all our requests. Highly recommend this place and will definitely stay here again!"
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Waterfront Beach House
9.6 out of 10, Exceptional, (38)
"This was perfect for us. We had a family funeral and this was a nice retreat. We would stay again for sure. "
Waterfront Beach House
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (33)
"We had a great holiday weekend at this clean, comfortable and spacious home. The property was exactly like the photos with plenty of comfy accommodations for our large group. Lots of thoughtful touches for guests and great local recommendations helped to make our stay extra memorable. The little ones in our family didn’t want to leave. Thank you!!"
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, (84)
"We liked the house which is ideal for a large group. But we were disappointed that the water views shown in the photo gallery did not exist as views from the house directly. "
The price is AED 547
AED 1,580 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Historic Essex Home w/ Large Yard Near Downtown!
9.8 out of 10, Exceptional, (40)
"All bedrooms up were difficult with luggage. Fully equipped for an extended stay would be convenient. Very close to marina and shopping."
Historic Essex Home w/ Large Yard Near Downtown!
Coastal Retreat: Waterfront, Deck, Awesome Views
10.0 out of 10, Exceptional, (12)
"It was a great week on the water front. Incredible view on the water, close access to the beach friendly neighborhood. "
Coastal Retreat: Waterfront, Deck, Awesome Views
Quaint Family-sized Home w/private beach — 5 minutes from wineries!
9.6 out of 10, Exceptional, (10)
"Excellent "
Quaint Family-sized Home w/private beach — 5 minutes from wineries!
Northfork Townhouse- walk to all/ newly renovated
9.0 out of 10, Wonderful, (2)
"We had a great stay at this house! Host was incredibly communicative and kind. House was exactly what was picture in the photos. Short (and beautiful) walk to all the restaurants and shops in town. Book this place now!"
Northfork Townhouse- walk to all/ newly renovated
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
10.0 out of 10, Exceptional, (13)
"Cute bungalow in a fantastic location - very close to a lovely private beach. Close to town and farm stands a well. Superb location. One note- the second bedroom does not have airconditioning- fans are provided but could get warm if outside temps are high. "
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
10.0 out of 10, Exceptional, (6)
"Great bungalow for weekend getaway. New building with spacious shower and access to pool and hot tub. In a very quiet area of Bridgehampton with close access to restaurants and shopping. Host was very responsive and helpful. "
The price is AED 716
AED 1,420 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
10.0 out of 10, Exceptional, (18)
"Exceptional property, extremely well designed, location is outstanding; it is a true Hamptons Estate fit ideally for family stays and relaxing experience. "
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
10.0 out of 10, Exceptional, (11)
"The house is very nice. Very updated and clean. Best bathrooms in any house we have stayed in. The kitchen was large and very nice. Backyard is nice and private with plenty of room. My only issue is that there are so many trees that it blocks a lot of the sun. The pool is in the shade most of the time. In the hot summer it might be great to get some shade but our week was in the low 70's and we could have used a little more sun on the pool. House is in a good location, close to town and the...
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Beach House
9.8 out of 10, Exceptional, (47)
"It's Christmas all year and we loved it! So so cozy. From my elderly mom to my toddler everyone was happy. Kids lived the playground and we loved how easy and comfortable the house was. Joe also left us delicious cookies from a local bakery. Thank you Joe!!! "
Beach House
5 bedroom Private Family Get Away w/ Heated Pool
10.0 out of 10, Exceptional, (13)
"We were a group age 3 to 75! The house was clean, well stocked and things for everyone’s interest. Our host, Carrie, was kind and responsive. It will be a beautiful memory of spending time with our children and grandchildren. "
5 bedroom Private Family Get Away w/ Heated Pool
Fall in the🌅beautiful sunsets
10.0 out of 10, Exceptional, (24)
"Margaret is just wonderful. We felt like we were staying at a dear family member’s home. Stayed in her very private upstairs suite and it was perfect for me, my wife and our pup. He had a blast running around the yard, meeting the chickens going to the bay beach etc. We had the best time! Thank you Margaret!!"
Fall in the🌅beautiful sunsets
Beautiful remodeled 2 bedroom home — 5 min from the beach! 20 percent for week
9.8 out of 10, Exceptional, (20)
"Great experience. The house was clean and the location was perfect for what we needed. "
Beautiful remodeled 2 bedroom home — 5 min from the beach! 20 percent for week
2 Bedroom Hamptons Waterfront Cottage Rental
10.0 out of 10, Exceptional, (10)
"Everything first class. Air co and heat units in each tooth Everything thing you might need for a great vacation "
2 Bedroom Hamptons Waterfront Cottage Rental
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
9.4 out of 10, Exceptional, (33)
"The backyard with ocean frontage is spectacular. We loved sitting in the rocking chairs watching the sunset as well as early morning fishermen. On arrival, the property was not clearly marked with a number and maneuvering the neighborhood was confusing. We love the quaint antique decor. However, the kitchen area was not as clean as we would have expected."
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
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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Other property types in Southold

Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (258)
"Very private"
The price is AED 484
AED 632 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
Windward Shores Ocean Resort
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (204)
"Beautiful accommodations, friendly staff Excellent communication and very clean "
Cliffside Resort Condominiums
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, (163)
"We had an amazing stay at this Vrbo property! The home was incredibly clean and spacious, offering more than enough room for everyone to feel comfortable. It was beautifully furnished, making our stay both luxurious and cozy. The location couldn’t have been more perfect, close to everything we needed yet in a peaceful neighborhood. Communication with the host was seamless—quick responses and very accommodating to all our requests. Highly recommend this place and will definitely stay here again!"
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
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.