Vacation rentals with beach access in Shelter Island

Nice little Bungalow! Perfect for up to 4 people. Very private and clean. The Location was Great. Right across the street from the Beach with a beautiful view. Has a small Firepit. Only a mile or 2 to Downtown. Would definitely go back.

Cozy, well appointed apartment on a tranquil property in the woods. Short drive to the woods and to downtown Sag Harbor. All in all, a great pied-a-terre for our week in the Hamptons.

My girlfriend and I stayed here for a weekend in late May. The complimentary beach pass parking is nice, would love to have been here in the summertime. Cozy bed and very clean place. TV has all the apps. Food in the area was a bit hit or miss but I suppose it is the Hamptons.

this was my 4th time staying at this air b and b and as usual I dodnt want to leave!!. Sarah and Phil where amazing. I love going to this air b and b becouse its so peaceful and calm and its like be at home. I will be back again. if you looking for an awsome place to stay look no futher!!! this is thr place to go!! this family is wonderfully and beautiful people. I will be booking again. thank you again for being such an amazing host.. its like staying with family...thank you 😀😀😀..

Claire's place was the perfect spot for a weekend getaway. It was very clean, cozy and nicely situated on a peaceful street in walking distance to the LIRR train station, the main street in Southold, and a lovely beach with stunning views of the Shelter Island Sound and its surroundings. I would definitely book again!

Lovely place! We enjoyed our stay. So close to everything Greenport has to offer!

Melissa is a great host. This is a prime location within walking distance to downtown, and close to a beach and park. We would stay here again.

Anastasia is a wonderful host. Will keep this listing handy whenever we need accommodation again.

Erica and Janson's place was perfect for our group of eight to attend a wedding in the Hamptons. You cannot get closer to the North Ferry to Shelter Island and there are many restaurant and shopping options within walking distance... the pizza place next door is open late, PORT restaurant (across the street!) is great for waterfront drinks and dinner. While we didn't use it, the LIRR station from Manhattan is also 500 feet from the front door. Ample parking was appreciated and the place was spotless. Thank you Erica and Janson!

The Navy House was the perfect place for our girls weekend in Greenport! Beautiful home exactly like the photos, clean, and in a lovely neighborhood that is walking distance for a fun night out. Would definitely recommend and book again!

Anne Marie’s cottage was exactly as described right along w/the peaceful surroundings, lovely views of the water and close proximity to beach and town. She gave us recommendations for local gems, and we thoroughly enjoyed our time. We will certainly try to get back again. Cheers to the host 🥂

We had a wonderful weekend. Great place to stay. Would recommend it highly.

Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.

Charles place was perfect for a girls weekend. We loved how easy it was to walk into town. Having the little outdoor space was wonderful to relax with coffee or wine. Loved the bunk room to make us feel like we were back in college. Would go back again!

My husband and I had a lovely stay. The house was exactly as you see in the photos and located on a quiet, tree-lined street, an easy walk to restaurants and stores. We were blessed with beautiful weather and particularly enjoyed the sun-lit rooms in the morning. Great mattress, nicely renovated bathrooms, and very clean. It was too early for the pool but my husband enjoyed sunning on the pool deck. Overall, we really felt you couldn’t beat the location. Highly recommend.

We had a lovely fall weekend stay at Paul’s place. The house and the water views are just as pictured. Convenient location allowed us a good home base to explore the north fork wine trail and local businesses. We did have one small plumbing issue during our stay however Paul was extremely responsive to ensure it did not affect our stay at all. It was a nice experience having such a responsive host. Overall our friend group had a great time and would return again.

This was a wonderful place to stay! The rooms were clean, and the ocean view was absolutely beautiful. 10/10 — I would definitely return!

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!

Mia’s place is excellent. Exactly what the listing describes and more — Mia is a great host and super attentive despite us being a last minute booking, she even helped us through a tough time late in the day when I thought my daughter’s stuffie had been picked up by the maid service. Above and beyond!

We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.

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.

George was a wonderful host , so available and willing to help with local knowledge and suggestions. The Condo is beautiful with a stunning sea view and plenty of amenities. I would definitely recommend this place to all .

Tara’s place was a perfect for a weekend getaway! Close enough to town and great view of the sunset!

Had an amazing stay in Greenport. The condo was exactly as listed, extremely clean and has a ton of amenities. Tom communicated from when the reservation was booked until the end, he was readily available, answered quickly and gave tons of informations. The location is ideal with the private beach and pool and a quick 5 minute drive into town. The condo offers a great little kitchen, a wonderful balcony with a water view and an unbeatable sunset and all the amenities you need for your stay. Pool towels are provided, plenty of bathroom towels, there’s a coffee machine, 3 tvs, a variety of dishware and there’s coin operated laundry in the basement. The staff that works the grounds and property are also super friendly. The town of Greenport and other surrounding towns are all close, you have endless options for vineyards in close vicinity and there’s tons of amazing restaurants within a 5-15 minute car ride. I highly recommend booking this property, I will definitely be rebooking! (If yo