Vacation rentals with beach access in Shelter Island

I had an amazing stay at Krae’s beach house in Montauk! The location is perfect, just a short walk to the beach and close to Montauk town, making it easy to explore the area. The house itself is beautiful—tastefully decorated, clean, and well-maintained. The kitchen was fully stocked with all the amenities we needed, which was great for cooking meals. Krae was incredibly responsive and accommodating, even allowing flexibility with check-in and check-out times. Overall, it was a fantastic experience, and I can’t recommend this place enough!

great place for a weekend getaway from the city! Zoi was very communicative and helpful!

Great place with lovely accommodation

We enjoyed our stay at Samantha and Robert’s place. Convenient location, close to downtown and the beach. The place is spacious and cozy. Samantha and Robert provided us with everything we needed.

Had a great stay, very clean and peaceful apartment, host was super responsive. Would definitely stay again!

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!

I have stayed with them before and they are very friendly and responsive. The apartment is clean and comfortable. I would stay again

Lovely, clean, comfortable, well-designed space. Hosts are friendly, responsive, and respectful of guests’ privacy. Would stay again!

This is an absolutely beautiful home. It felt warm and cozy from the minute we walked in. Marla was kind enough to let us check in early, which allowed us to get the most of our first day in the Hamptons. She responds very quickly when you reach out. The location was perfect. It is very close to so many things to do. The neighborhood is lovely and quiet. The house is beautifully decorated, very clean, plenty of room and has everything you need. I would highly recommend this home!

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!

My family had a wonderful time at Robert’s home. The house was clean and cozy and the view of the water was peaceful. He was super communicative and friendly and check in/out was a breeze. The house is in a great area and super close to East Hampton, Amagansett, and Montauk. Highly recommend!

Close to water! Comfortable sofa! Restaurants you can walk to ! Enjoyed our visit with family!

We were gathered from around the country for my Mother s Memorial. It was such a pleasure to stay in such a peaceful environment, as emotions were high. It was healing. Beautiful home, and all directions were clear. If it had been a little later in the Spring and the weather warmer, it would have been even better. I highly encourage anyone to stay and enjoy what the area has to offer in Gregory's beautiful home. You will have a wonderful vacation!

We loved Leslie's place and would book here again in a heartbeat - especially in beach season (we were there mid-April). We opted for Leslie's because of its great location over a much larger home with more amenities in the same price range - we were not disappointed! We have two teenage boys and we felt comfortable letting them explore the neighborhood on their own while we squeezed in a few hours of work. Walk or bike to beach, park, basketball courts, restaurants/bars, laundry and more. Encountered many friendly neighbors on our walks. Average 15 min drive to explore lots in West Haven/New Haven. The deck is almost as large as the house with a grill and great furniture. The fully fenced yard was perfect for our dog - even she felt right at home immediately! The inside is nicely decorated and very comfortable. I loved having my coffee/beer/ cocktail on the deck in view of Long Island Sound with my dog sunning herself by my feet! I highly recommend for couples or families of all ages!

The house was gorgeous and such a beautiful location and time of year to stay. Highly recommended!

We needed a dog-friendly ranch style to home with three bedrooms and two bedrooms close to Sayville, where we would be celebrating Thanksgiving. I was lucky enough to find this rental which was clean, comfortable and ideal for our two-night stay. Adam was attentive and easily accessible via text. I would highly recommend this lovely home.

A brief stay but a great stay. It was offseason but we got lucky with sunny October weather. The stay was less than a 5 minute drive from the main village with tons of shops, cafes, etc.. the room itself had a beautiful ocean view and was very clean and comfy. Nice shower, comfy beds, plenty of linens and towels provided. Parking included. Overall a very nice stay.

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!

We had an amazing stay! We stayed off peak season, although alot was closed we felt right at home and were more than happy to spend family time at this condo! The views were stunning, and the condo was immaculate. We were close to everything and was still within very reasonable driving distance to the surrounding towns. Julie was a pleasure to work with and was always very responsive and accomadating throughout the process. Hoping to stay again next year!

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.

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.

Our second time renting a condo at Rough Riders in Montauk. Contrary to the name, there is nothing rough about this picturesque location with unobstructed views of the ocean, pier and wonderful wildlife everywhere. The condo we rented Sept 30 -Oct 2, 2023 has a well appointed kitchen with new amenities, including a pot filler faucet over the stove! Pristine/clean condo and lovely deck for lounging w/ book and coffee. The couch is very comfortable and the master bedroom has plenty of closet and bureau space for longer stays. The 2nd bedroom has bunkbeds so not ideal for two couples but perfect for small families. The television was a little tricky (if you bring tv-loving kids). Not walkable to downtown but theres at least one restaurant/bar just outside the entry to this gated community. Short drive to shops/restaurants in downtown Montauk. Horse lovers call Deep Hollow Ranch in advance to book truly memorable trail rides. Enjoy!!

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

The place was perfect nice and clean what I like the best is the it was close to the beach to go for a walk.