Beachfront vacation rentals in Southold

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Popular amenities for Southold beachfront rentals

Pet-friendly beachfront home rentals

Superhost
Home in Woodmont
4.92 out of 5 average rating, 25 reviews

Beachfront getaway in Milford

AllisonRating, 5 stars10 months ago
My husband and I stayed here with my mom, 3 yr old, and infant and had a lovely time. The house had everything we needed and nothing we didn’t need. This place was no frills but right on the water, and the price reflects that. Stairs are a bit on the steeper side so just be aware of that if you have anyone with bad knees or children learning to use stairs still. Our host was wonderful and very responsive, we liked him a lot! The beach out front is a bit rocky, so water shoes are a must. But it is so beautiful and peaceful! Our favorite thing was going out during low tide with the kids, you can walk really far out and we saw lots of horseshoe crabs and it was so much fun.
Top guest favorite
Home in Milford
5 out of 5 average rating, 103 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

BethRating, 5 stars1 week ago
Amazing place to stay! This spot is spacious and charming with everything you could possibly need to relax in this beach town getaway or explore. Our hosts were so helpful and welcoming!
Top guest favorite
Home in Milford
5 out of 5 average rating, 103 reviews

Milford Beach House - Newer Construction!

SabrinaRating, 5 stars1 week ago
Victor and Kim were gracious and amazing hosts. I was celebrating my birthday and they even had a card, a bottle of champagne, red wine and fruit. It was such a wonderful surprise! The house was so beautiful and the beach is just outside! The kitchen was fully stocked with everything one would need to cook for a family; there was a convection oven! We loved using the grill as it was memorial day. Bathrooms had rain showers. Beds were so comfortable and it was truly wonderful to wake up to a beautiful sunrise and to just listen to the waves from the deck or even the living room. We spent a lot of time outside, on the beach. It was home away from home.
Superhost
Home in West Haven
4.79 out of 5 average rating, 107 reviews

Cozy Home, Dog and Family Friendly - book today!

JanineRating, 5 stars3 weeks ago
It was a perfect stay for my sons graduation weekend. The check in was easy- there were enough beds for 8 of us. On sunday we took a walk to the beach. Even our pups had a good time. THe inside was nice and clean. It was just as described.
Top guest favorite
Home in New Haven
4.95 out of 5 average rating, 112 reviews

Beach Haven - waterfront, near Yale, sunsets

JamesRating, 5 stars1 week ago
Home right on top of a sea wall with stairs to the sandy beach at low tide. Great to have coffee in AM while watching the ocean from the enclosed porch. The airport is very close though we never heard planes in the home. Hosts were very responsive and helpful when booking and for checkin.
Guest favorite
Cottage in Milford
4.95 out of 5 average rating, 319 reviews

Spring Sale|CozyCottage|Pet-friendly|Walk to Beach

CourtneyRating, 5 stars3 weeks ago
Cameron’s place was very clean and true to the photographs. Check in process was contactless and easy. Cameron reached out several times throughout the stay to make sure everything was going well. Check out process was clearly communicated and easy as well. It would be great if there was a full length mirror, but that would be the only feedback we had. Thank you!
Superhost
Home in New London
4.85 out of 5 average rating, 172 reviews

The Classic #1 @ Ocean Beach: 6 Queen 1 Sofa Bed

ChristopherRating, 5 stars1 week ago
Absolutely perfect. The house provides everything we needed for a great visit. Easy walk to the local beaches. Would definitely return if given the opportunity.
Superhost
Home in Woodmont
4.91 out of 5 average rating, 35 reviews

#MilfordOceanView - Beachfront, Dog Friendly

AslynnRating, 5 stars6 months ago
Thank you for a wonderful stay and accommodating an extra night.

Beachfront home rentals with a pool

Superhost
Home in Hampton Bays
4.88 out of 5 average rating, 32 reviews

Close to Beach | With Pool | Hampton Bays

JulieRating, 5 stars1 month ago
Andrew was a responsive communicator and we had a lovely stay at this very charming, clean, simple apartment. Bathroom is upstairs and laundry is downstairs just fyi if mobility is an issue. We loved that you could walk out the door and into the water immediately. Beautiful weather and views when we visited in April.
Superhost
Condo in Hampton Bays
4.78 out of 5 average rating, 23 reviews

Waterfront Elevated Bungalow - Spectacular Views

SteveRating, 5 stars56 months ago
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.
Guest favorite
Home in Hampton Bays
4.97 out of 5 average rating, 59 reviews

4 BR Hamptons Oasis w/ Pool,Jacuzzi & Beach Access

MariaRating, 5 stars3 weeks ago
What a dream stay! From the get go Vanessa was responsive and helpful with the booking. Our Girls Gone MILD Bach trip needed a home that would keeps us in vs out and this GORGEOUS home with it’s beautiful garden and pool/jacuzzi/patio made it the most memorable stay. We loved playing board games in the living room and dining at that warm long table! The kitchen was fully equipped with everything we needed as well (plenty of wine glasses for all the Wolffer Rose we got) and don’t get me started on the book in the basement rooms. There were towels, beach gear, umbrellas, and all the things you could possibly need for an unexpected rainy day or to have a good time at the pool/beach! Also the walk to the public access to the private beach was a short walk through such lovely neighborhoods! I’m hoping to come back and stay here again! The girls and I loved waking up to the pristine garden views and the occasional bunny that would hop across the lawn! We were definitely sad to leave ˙◠˙
Superhost
Home in Woodmont
4.84 out of 5 average rating, 88 reviews

Spacious 4 bedroom, oasis with ocean views galore

JoetteRating, 5 stars1 week ago
Allana was very easy to work with. Always answered back quickly no matter the time. Open concept and everyone was able to be together. It was a rainy stay so had to be inside. No one minded. Nicely set up for games or conversations. Thank you so much!!
Guest favorite
Apartment in Montauk
4.9 out of 5 average rating, 10 reviews

Oceanfront Corner Studio Bungalow on the beach

EdRating, 5 stars2 weeks ago
Loved Samy’s corner unit, which gave us a bit more privacy and quiet than other parts of the property. The studio was as described, with great light and well-cleaned prior to our arrival. Enjoyed use of the tennis courts every day. Only minor disappointment was that we were not yet allowed to use the pool, which we were told would be ready by Memorial Day (we were there one week prior). Still, a worthwhile stay and I’d come back and recommend it to others.
Superhost
Apartment in Montauk
4.85 out of 5 average rating, 39 reviews

Montauk Ocean View One Bedroom

GiovannaRating, 5 starstoday
Love my time at the wavecrest! Will definitely comeback and stay longer :)
Top guest favorite
Home in Bellport
5 out of 5 average rating, 16 reviews

Private oasis with pool steps away from the bay

MitchellRating, 5 stars7 months ago
I cannot describe accurately how lovely and comfortable Jonathons house is It was more than perfect for us in every way! The fenced in yard was perfect for our little dog and we all enjoyed turkeys and deer hanging out. Walking the neighborhood and to the beach with leaves changing It couldn’t have been any better.
Guest favorite
Home in Hampton Bays
4.91 out of 5 average rating, 54 reviews

Hamptons Round Beach House - 60 secs walk to beach

MatthewRating, 5 stars8 months ago
The pictures really don’t do this beautiful house justice. The property is extremely private, peaceful, and a few hundred feet from the beach. The kids absolutely loved the pool/jacuzzi. The house was fully equipped with every amenity and we were well covered for cooking meals. The house itself is unique, quirky, and functional. The bedrooms were all very clean and comfortable. Jeanne was also very communicative throughout our stay. Would definitely recommend.

Private beachfront home rentals

Guest favorite
Cottage in Branford
5 out of 5 average rating, 10 reviews

Beachfront Cottage Serene Private Beach, Kayaks

BasilRating, 5 stars9 months ago
We loved it. Redefines “fully stocked” - David’s place had everything we could ask for. The water at high tide was magical. Kayaking, fishing and we found over 100 (literally) hermit crabs.
Superhost
Home in East Haven
5 out of 5 average rating, 56 reviews

Direct Waterfront Home Located on Private Beach

MilenaRating, 5 stars5 months ago
Great location with amazing views. I can only imagine how lovely it would be in summer for a little getaway. .
Guest favorite
Home in New London
4.9 out of 5 average rating, 10 reviews

Paradise on Pequot

KyleRating, 5 stars9 months ago
A perfect long weekend getaway for my wife, 2 toddlers and infant. Relaxing and great location. The little beach access just a short walk away was amazing. Already thinking about going back.
Guest favorite
Home in Mastic Beach
4.98 out of 5 average rating, 40 reviews

Mastic Beach Surf House

ThomasRating, 5 stars1 week ago
We had a wonderful stay at this cozy, newly remodeled home in Mastic Beach, NY. The house was spotless, fully equipped, and located on a quiet street—perfect for a relaxing getaway. Each bedroom was comfortable with its own AC/heating unit, which made it easy to keep everyone happy. The owner was incredibly kind and accommodating. The only small downside was that there was no washer and dryer available for use. Otherwise, everything was fantastic. Highly recommend this place for a peaceful and comfortable stay!
Superhost
Cottage in Milford
4.76 out of 5 average rating, 33 reviews

Cheerful 2 bedroom cottage on beach

MatthewRating, 5 stars10 months ago
This house is absolutely perfect. It's clean, charming, has everything you need. The beautiful back yard has plenty of space and good stuff for kids to play with. Also, it's about a 30 second walk to the beach... neighbors are out on their patch of beach but yours is yours to yourself. It's perfect. We cannot wait to come back.
Guest favorite
Home in West Haven
4.95 out of 5 average rating, 21 reviews

Beach House steps from sand & Amazing Views

LeeAnnRating, 5 stars3 weeks ago
We stayed at Adam’s beach house in West Haven, CT with our extended family to celebrate our daughter’s college graduation! The 5 bedroom house was even more beautiful than the pictures! And the ocean view- was absolutely stunning! Every bedroom was perfect and the bathrooms have every amenity imaginable! We arrived on Friday, celebrated the graduation on Saturday, and enjoyed the beach on Mother’s Day! We checked out on Monday. Adam is a super host- very welcoming, generous with check in and check out times, and responsive to any questions! Thank you, Adam, we really enjoyed our family time at your beach house!
Guest favorite
Home in East Lyme
4.96 out of 5 average rating, 190 reviews

Beachfront Paradise

SandraRating, 5 stars3 days ago
I went there to relax and to see and hear the ocean... it didn't disappoint... Not only sand and ocean waves, but I got a birds-eye view of a small members only marina (dealing mostly in sailboats). Plus the added enjoyment of watch boat traffic since we're close to NY and the islands. Plenty of beach to play on and constant sm wave action. Lots of restaurants, stores and Costco all within 15 minutes of the house if you need something. I would definitely return to enjoy this sanctuary. Sandy Y. Manchester CT
Guest favorite
Home in Milford
5 out of 5 average rating, 9 reviews

Renovated House on Private Cedar Beach

PeterRating, 5 stars8 months ago
The house was perfect and what we expected for a quick couples getaway. Steps from the beach. good local restaurants. Close enough to concert venues without having to stay in Bridgeport.

Quick stats about beachfront rentals in Southold

  • Total rentals

    30 properties

  • Nightly prices starting at

    $110 before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

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  2. United States
  3. New York
  4. Suffolk County
  5. Southold
  6. Beachfront rentals