Holiday rentals with beach access in Shelter Island Heights

⭐️⭐️⭐️⭐️⭐️ Clean, Comfortable, and Thoughtfully Prepared! We had a great stay! The place was spotless, quiet, and exactly what we needed for a few nights of good sleep and hot showers. It was clear that the host put thought into making guests feel welcome—there was a mini chocolate bar and a bottle of water waiting for each of us when we arrived, which was such a kind touch after a long day of travel. Check-in was smooth, the bed was comfortable, and everything worked perfectly. While we didn’t spend much time there beyond resting, it was the perfect place to recharge. Highly recommend for anyone looking for a clean, convenient, and cozy spot!

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.

Sam's place exceeded our expectations! The view was marvelous, and the house was beautifully decorated with a wonderful collection of books we truly enjoyed. The kitchen was fully equipped with everything we needed, and the room was super clean. We had a great time during our two-day stay. The small town offered so much to explore, and the nearby seafood market was a delightful surprise. we had fresh lobster at a very reasonable price. We highly recommend Sam's place for a relaxing and enjoyable getaway!

I love this place. Perfect but what we were looking for. Walking distance to access beach. Overlooking the pier. Very clean and check in with.

Alisa and Lena's place was really cute, private and comfortable. We had everything we needed for our 2 night stay. Also you can walk a few short blocks to a bird sanctuary!

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!

Dawn and Bob’s place is one of the top Airbnb’s we have stayed in! Top notch in every way. It was spotless, comfortable and had everything we needed. And on top of that Dawn and Bob were the most friendly hosts we have met! I would recommend this Airbnb without reservation and will be back whenever we are back in CT!

Wonderful and cozy apartment! We were in town for a wedding and needed a clean and safe space to make home base. This was perfect. Would absolutely stay again!

Maura is an amazing host! She is super friendly and helpful and personable. The house was beautiful and very clean and the location was perfect! I would/will be booking it again in the future.

Kristin’s house was perfect!!! It was even more beautiful in person and had absolutely everything we needed to have the best stay at Greenport! Not only was it beautiful, but it was also in the best location, making it easy to get to and from the Main Street and wineries! I traveled with 8 friends and we all said we’d book again without a doubt! Thank you Kristin for an unforgettable stay!

Dave was an amazing host. Incredibly responsive, everything was clearly communicated, and very helpful. The house was perfect for our family--great location near the beach with shops/restaurants nearby. Highly recommend!

Ann Marie must be one of the top hosts on the app. She was the most responsive and caring person assuring our stay was up to her high standards. The property was suited our needs very well, was close to the beach, and only a short drive away from the main strip in town. Everything was clean and prepared for our arrival with meticulous attention to detail. We would certainly stay here again in the future!

Xiao is a very good host with flexibility, easy to communicate with. The house is in the woods, not by the beach (in case anyone wonders), but has key access to the nearby private beach which is really nice.

Our group of 4 had a great stay at Riley’s! Location was super convenient, check in could not have been easier. We loved sitting on the deck outside and making an outdoor fire. Thanks for a great stay!

We had a wonderful two day stay at Roger and Amy’s place. It was fantastic- such a beautiful, inviting home. Our kids had a blast in the heated pool- we could barely get them to come out despite it being under 60 degrees out! The kitchen was stocked with more than just kitchen basics- the spice cabinet had soo many different choices ! It was probably the most perfect AirBnb experience I’ve had and we travel plenty.

Una casa bella para pasar siempre con personas importantes.

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

Met all of our needs to be close to family in the area for an event. It's very spacious and the beds are comfortable. The spiral staircase was steep and narrow, but we made it work. Thanks for a great overall stay!

Really great stay. Apartment was perfect for us. Less than 5 mins walk to the beautiful beaches and small town. Would stay again!

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.

Lauren was great and her home was exactly as promised! Great stay and will stay again!

Had a great experience in the space! The host was very helpful and everything worked out perfect.

Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!