
Apartment holiday rentals in Southold
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Top-rated apartment rentals in Southold
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Holiday rentals for every style
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Popular amenities for Southold apartment rentals
Weekly apartment rentals

Water front, sunsets, sail boats, Wi-fi, birds
John and Cathy are amazing hosts. This was our second consecutive summer stay in their condo and it does not disappoint. The place and the amenities they provide are amazing and they are a wonderful couple who respects your privacy but are there for anything you need. I recommend anyone to stay here and know they would want to return. Thank you John and Cathy for making our second summer with you a fantastic vacation!

Beautiful condo on Long Islands Northfolk
We very much enjoyed our stay at the Cliffside for our wedding weekend! Alice was very flexible with us, which we appreciated because getting married is chaotic enough LOL. Would highly recommend staying here. The unit was spotless and had a wonderful view. We could not have asked for a better stay!

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.

Beautiful Waterview Condo on the North Fork of LI
Great retreat for a long weekend. Enough space for family of four. Easy access to everything in the Greenport area. Mia was very responsive, and the place was great. We would stay here again!

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.

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+

A Unique Piece of Paradise, Water Front pool
This was my second time at Susan’s. The location on the bay with the beautiful views and sparkling clean pool will bring me back again. The house is always extremely clean and comfortable. Great location to walkable Rumba’s Restaurant. Susan is very reachable and a pleasure to rent from. I highly recommend it.

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!
Apartment 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

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.

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

One Bedroom with Loft, Balcony with Ocean Views
A great property and an excellent unit. Ocean Dunes is a jewel in the Hamptons! We look forward to our return!

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!

Modern Two Bedroom Apartment. Beach Ready!
Private apartment rentals

Cliffside Resort Poolside Condo A101
Really liked the place but our reservation didn’t end up getting entered into the Cliffside system - so I had to call the after hours emergency service to get the code to get in. Not a huge deal but a little scary,

Two Bed Corner Condo I Incredible Sea views!

Cliffside Resort I Water View 2 Bed Condo

Seaside Escape I The Cliffside Resort Exclusive
Quick stats about apartment rentals in Southold
Total rentals
20 properties
Nightly prices starting at
$154 SGD 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
Destinations to explore
- The Hamptons Holiday rentals
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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