
Waterfront vacation rentals in Southold
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Top-rated waterfront rentals in Southold
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Popular amenities for Southold waterfront rentals
Waterfront apartment rentals

Stony Crk Studio ideal for trvl nurses…
Great stay in Stony Creek Village with a view of Long Island Sound and short walk to the pier, Stony Creek Market (breakfast & lunch). I used the Library and went to services at the Stony Creek Congregational Church. Overall, a nice experience.

Sugarloaf Annex
Really cute and clean place, so happy we stayed here! It was perfect little place for a getaway to relax, even in the winter months. Everything inside was up to date and it had everything we needed. It even looked better in real life than the photos. Highly recommend!

Bayside Boho Retreat
This is our first AirBnB experience. Communication with KC in advance was great. The place is very nicely decorated, so we felt very comfortable right away. Our children liked the children's room very much and I liked the veranda. Our kids are very bright and loud and that's certainly a challenge for hosts. We are therefore glad that there were no complaints. The area is very nice and quiet. We will be happy to come back.

Private waterside retreat- Vineyards/Outlets
What a beautiful home. It is located in a park like setting, so peaceful and quiet. We were visiting family and the location was perfect for us. We would highly recommend this property and we will use it again ourselves.

Amazing Greenport Village Apartment in CENTER!
Just as expected. Our second time staying there. Recommend for an affordable stay in a great location!

1870 Sea Side Comfort
Charming young man the host was. Everything was perfect. I was staying as a traveling nurse and the home was a convenient and safe location to work. The house had everything I needed. Will be sure to stay again!

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Amazing views! Beach. Glamping. Camp store and great pizza place.

Swan Cove by The Sea - Boots & Saddle
Raquel and Warren were outstanding hosts. I loved staying at the Cottage and it was very quaint. I loved the neighborhood and there is a great restaurant within walking distance.
Waterfront house rentals

Casa al Mare Beachfront Retreat Oceanview
Perfect venue for a Thanksgiving getaway with our whole family. Rather than having out of town family staying at hotels, we could all stay together in a comfortable home with a beautiful view.

Mastic Beach Surf House
The place was absolutely beautiful, clean and had great amenities. The host was also very responsive and attentive to any questions we had to ask. Would come back in a heartbeat!

Luxurious Waterfront Beach House On The Bay
We had a wonderful stay at Steve and Dorry’s place! The living room and kitchen is surprisingly spacious and feels so open & inviting because of the outdoor deck space and view of water. We hope to be back again!

Waterfront with private dock & bocce court
We thoroughly enjoyed our stay and would definitely book again ! Close to the many wineries and cute towns, and peaceful and comfortable to come back and relax at. We enjoyed the fire pit , the view from the dock of the changing tree colors and the flow of the kitchen. ❤️

Private beach, fully updated cottage, on 2 acres.
This home is beautiful and so spacious! Proximity to East Hampton and Springs, yet very private and peaceful. Couldn’t recommend enough!

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
Had a wonderful time over Easter with my family and dog. The view was exquisite and the house very comfortable. Eileen was very responsive and even had hair dryers sent over. The house was very well equipped with lots of kitchen staple goods. Just be aware there is no microwave, but there is a very nice Breville toaster oven. Also, there is a large table outside for a group, but only a small table and counter seating in kitchen inside. We didn't have any issue since the weather was perfect for us to enjoy our Easter dinner outside. Overall, a beautiful home and only minutes from Greenport and wineries.

Beach Haven - waterfront, near Yale, sunsets
It is a charming place back into the water. Love listening to the sound of the ocean and watching the sunset and the noght light on the other side of the water.

Gorgeous Waterfront and Indoor Pool Family Oasis!
Five stars doesn't feel like enough, if anything I'd say everything was better than we'd expected based on the pictures and the reviews! First, as others have mentioned John was an incredible host, the place was well stocked and had all sorts of snacks and drinks (and a nice bottle of wine); he also bought us dinner and was very good about keeping in touch the whole time we were there. The house was amazing top to bottom, but I have to specifically call out the pool, which was jaw-droppingly beautiful and the perfect temperature despite cold weather outside. We loved the neighborhood and yard to walk our dogs, and the kitchen was great to cook in (made me miss having a gas stovetop). We'll definitely be visiting again, it was the kind of stay that sets a new bar for what to look for in a vacation!
Waterfront condo 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
This was the perfect last-minute getaway for my always on-the-go family in need of some quiet bonding time. The condo was simple and clean, the beach beautiful (even in the winter), and Alice and Gasper were very responsive. Would highly recommend!

Beautiful Waterview Condo on the North Fork of LI
Such a beautiful condo by the water! Too bad we stayed in November, we would have enjoyed the terrace way more! Mia was so responsive and helpful with my questions prior to the weekend at her place.

Oceanfront Condo - Incredible Spring Rates!
My stay at Julie’s was wonderful, I was always able to message and get a quick response she was very accommodating. The view was beautiful and felt comfy like home. I will definitely be returning in the summer once it’s warmer !

Freeboard at Soundview · Beach+Ocean+Sunrise
Rate was great, it was off season. Cleaning fee is a little nutz considering it is tiny. VERY clean, perfectly functional. I wasn't a fan of the mattress, way too soft for me, but maybe that is just me :-) Overall I would happily stay there again. It was quiet, the other tenants were very friendly.

Beautiful 2 Bedroom 2 Bathroom Waterfront Condominium Getaway
Very clean and nicely decorated condo for our enjoyable weekend getaway. Would love to stay here again!

Hatch at Soundview · Beach+OceanView+Sunrise
Amazing little spot next to the beach ⛱️. The host were super sweet and very responsive to any issues we had. It's just as pretty as it looks in the photos. I had an amazing stay, would definitely stay here again.

Waterfront Condo C-204 at The Cliffside Resort
lovely 2 bedroom with gorgeous water views from two roomy terraces , nice to wake up to the breeze of the water and the unspoilt natural surroundings of the wild sound. Thomas was a great host and very responsive
Quick stats about waterfront rentals in Southold
Total rentals
70 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
2.1K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
20 properties have a pool
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Dunewood
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- TPC River Highlands
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Shennecossett Beach
- Connetquot River State Park Preserve
- Long Island Aquarium
- Attawan Beach
- Groton Long Point Main Beach
- Sunken Meadow State Park
- Steer's Beach
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