
Condo vacation rentals in Southold
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Top-rated condo rentals in Southold
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Popular amenities for Southold condo rentals
Weekly condo rentals

Stunning, Spacious, Spotless. Close to Yale.
Great spot and at a really good price. Was visiting for a Yale event and was near enough to feel close without being too close to downtown. The area around the place is also super cute and not one I had explored previously. Huge plus for some good coffee shops nearby and of course Pepe’s. Camila was a great and responsive host. 10/10 would recommend Camila and this spot.

The Anchor at Soundview · Beach+Ocean+Sunrise
Great! Met our needs of staying somewhere for a couple of nights while visiting the area. Just be aware that there are not that many restaurants and shops in the immediate vicinity so you may need to go to towns 30 or so minutes away.

Seaside Summer Escape: 2BR Waterfront Condo w/Pool
We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.

Waterfront Elevated Bungalow - Spectacular Views
If we don't give a good review, can we keep this to ourselves?! Patti was a perfect host; the views were fantastic, whether from the outdoor porch or inside through the French doors looking out on the water. Access to the small beach and pool were excellent and we were close to several good restaurants (many of which Patti suggested, including some on the water) for take-out during the pandemic. Wifi was great and everything was very clean and as advertised. We generally fly for vacations and long weekends but had to stay closer to home this year and this was a perfect choice.

Seashore getaway - CT shoreline
Lisa and I enjoyed our stay at Laurens place. Felt right at home. Very clean, open space. We had the best time and did not want to leave. We will be back for sure.

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath
Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+

Seaside Summer Escape –2BR Waterfront Condo w/Pool
We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!

Cute cottage apartment upstairs in Sag
We had a great time at Adam’s place! The apartment was cozy, clean, and comfortable — perfect for a relaxing getaway. It’s just a quick 5-minute drive to Sag Harbor, which made it super convenient.
Condo rentals with a pool

One Bedroom Apartment Nestled in the Dunes
if you are looking for private, quiet, tranquil, beautiful, relaxing stay. This is the place. Private beach with comfy chairs, umbrellas, amazing pool and views, felt like a nature preserve. Walk to town. Apartment was great. I'll be back

Charming Bayfront Condo
Stop whatever you’re doing in the area and take 10 minutes to walk across the street to enjoy the sunset. I guarantee it’s addictive. Spent a post-Labor Day weekend with some friends and had an amazing time. The condo is centrally located between downtown Southampton, Bridgehampton and Sag Harbor and all that those areas have to offer. Several beaches, both bay-side and ocean-side, are also close by, but we mostly ended up lounging by the pool. The condo itself is spacious which is only further amplified by the amount of natural light reflecting off the bright interiors that let you know you’re near the beach. There are plenty of towels—both bath and beach—and there is ample beach equipment that you can use. The kitchen is fully stocked for cooking/dining at home, and there’s an outdoor patio equipped with a grill and dining furniture. Hostess could not have been nicer or more responsive, so I will definitely want to stay here again.

Seaside Summer Escape –2BR Waterfront Condo w/Pool
We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!

Beautiful 2 Bedroom 2 Bathroom Pool-Side Condo
Stay was great and the place was very clean

Watersedge resort time share Westbrook ct
Andrew’s place was awesome. Just steps to a beautiful pool and the ocean! Couldn’t have asked for a better place.

Two Bedroom Lawn Side 1st Floor Condo!
This was a wonderful place to stay. Clean and just beautiful. The condo and the scenery. My family and I truly enjoyed our short stay. Only one night. Looking forward to coming again and spending more time

Cliffside Resort Poolside Condo A105
Beautiful stay at Cliffside! The photos don’t do it any justice!! The rooms were super clean and well decorated. Pool was great!! The beach was beautiful!!!! Loved this place!

Oceanfront Condo w/ Spectacular View Furnished
Private condo rentals

Bright and Airy One Bedroom Apartment in the Dunes
A fantastic place to stay in the Hamptons, a special gem of a place located in the Dunes of Amagansett, will be back every year!

The Anchor at Soundview · Beach+Ocean+Sunrise
Great! Met our needs of staying somewhere for a couple of nights while visiting the area. Just be aware that there are not that many restaurants and shops in the immediate vicinity so you may need to go to towns 30 or so minutes away.

Cozy one bedroom apartment in Wooster street
Maricela was very responsive and flexible throughout our stay and booking arrangements. Thank you!!

Cliffside Resort Poolside Condo A106
Very lovely place to stay. All the amenities you would need and a view of the water. With the exception of the keypad entry not working at the end of our stay (assuming it was just dead batteries), it was wonderful.

Sun Drenched Loft-City Living in the Country
This place is great in old-school AirBnB style. Feels like Nadine’s second home being shared with us. Quality finishes throughout, very well stocked in terms of glasses, plates, towels, etc. We came for a wedding but were able to have our own nuclear family reunion with three young-adult children coming in from around the country. The space handled us all with ease. The great room is spacious with a big table and even bigger sectional sofa. Just a great place to gather and hang out (which we did a little more than expected because of tropical storm Ophelia). We enjoyed the coffee and sandwiches across the street and brought in sushi and wine for one dinner, less than 5 minutes drive away. One quick note: 2 BRs not 3

Freeboard at Soundview · Beach+Ocean+Sunrise
This was a great place to reset. I will say, don't get intimidated when you 1st walk in. The floors are a bit wonky and the walls are very thin. But I never felt more at home than when I saw my space. The neighbors were so friendly and the walk to the beach was about a block. Though it was cold we truly enjoyed the beach. And walked down there multiple times a day. There is also a gas station and convenience store 3min driving and very walkable.

Hatch at Soundview · Beach+OceanView+Sunrise
We had a pleasant time at Peter's place. He was a great host and was very responsive. It was just what we needed for some rest and relaxation on the beach after a week of hiking in the white mountains. Would definitely stay here again!

The Bridge at Soundview · Beach+OceanView+Sunrise
This was such a beautiful place. I was surprised with how much space there was. Me and my family very much enjoyed our stay.
Quick stats about condo rentals in Southold
Total rentals
20 properties
Nightly prices starting at
G$25,097 GYD before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Wifi availability
20 properties include access to wifi
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- Shinnecock Hills Golf Club
- Walnut Public Beach
- TPC River Highlands
- Ocean Beach Park
- Dunewood
- Woodmont Beach
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Quotonset Beach
- Heckscher State Park
- Ninigret Beach
- Sunken Meadow State Park
- Outer Beach at Smith Point County Park