Condo holiday rentals in Shelter Island Heights

Very clean apartment! Easy check in/check out. Had a nice stay!

We had such a lovely stay! The space was spotless, cozy, and thoughtfully put together. The little kitchenette had everything we needed, which made meals so easy. Best of all, the location is perfect—just steps from a beautiful beach and a super easy, scenic walk to town. Highly recommend and would absolutely stay again!

Great experience

We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!

This was a great place to reset. I will say, don't get intimidated when you 1st walk in. The floors are a bit wonky and the walls are very thin. But I never felt more at home than when I saw my space. The neighbors were so friendly and the walk to the beach was about a block. Though it was cold we truly enjoyed the beach. And walked down there multiple times a day. There is also a gas station and convenience store 3min driving and very walkable.

Nelson was a great and very responsive host! I would stay here again and again, there’s even private gated parking behind the apartments.

We had a pleasant time at Peter's place. He was a great host and was very responsive. It was just what we needed for some rest and relaxation on the beach after a week of hiking in the white mountains. Would definitely stay here again!

This was such a beautiful place. I was surprised with how much space there was. Me and my family very much enjoyed our stay.

Great little getaway, only wish it could've been longer! My favorite part was having the outdoor deck with a place to sit and take an outdoor shower (plus the grill but we didn't use it). Would definitely stay here again!

Maricela was very responsive and flexible throughout our stay and booking arrangements. Thank you!!

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!

the unit was perfect for my husband and myself and was in a very good location by the ferry and restaurants. It even had a rooftop deck to enjoy our wine time. We were close to the beach. We enjoyed walking to the different towns especially Ocean Beach which had shops and restaurants to explore. Anytime we had a question, we were able to contact someone to assist us as this is the first time we used an ABNB. We would definitely rent this unit again.

The place was great!! Exactly what we were looking for and a terriffic location.

We stayed for a month in a 1 bedroom, 1 bathroom apt. in part of Anne's beautiful 19th century mansion. The Unit was the perfect size for my husband and me, and our 2 cats. Anne is an amazing host. She not only made us feel at home, but introduced us to fun activities, restaurants, museums, and sailing lessons in the area. Anne was easy to reach out to, and always responsive to our needs. Anne takes great pride in airbnb hosting, and has wonderful stories about local history and attractions. We definitely intend to come back for another stay with Anne in one of her apartments next Summer.

Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+

Jeff's place has a lot of character and is spacious. The setting is excellent, near the water, with Satterly Landing right down the road. We enjoyed our stay.

The Beach Plumb was lovely! Everything was as advertised. The distance to town and the beach, the spacious layout, and the amenities are among the things that made our stay great

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!

Mark's place was exactly what I was looking for to ring in the New Year in style, comfort and complete relaxation! I was able to start each day with a quiet cup of coffee and then head directly to the beach for a long morning walk (just a short drive away). Montauk Manor is an absolute hidden gem for a winter break and the indoor pool and hot tub are a rare find in the Hamptons. Check-in/out could not have been any easier and the Manor staff are wonderfully welcoming and friendly. There were still a good number of local shops open, including Left Hand Coffee. 100% recommend for all seasons and will eagerly book again!

Perfect spot for a Montauk getaway. Walking distance to everything dockside has to offer, great pool and lounge chairs on the property, very simple check-in via code with the front desk. Nick was kind and communicative our whole stay. We’ll be coming back!

We very much enjoyed our stay at the Cliffside for our wedding weekend! Alice was very flexible with us, which we appreciated because getting married is chaotic enough LOL. Would highly recommend staying here. The unit was spotless and had a wonderful view. We could not have asked for a better stay!

Great stay for a quick weekend getaway! Highly recommend as you are right by the beach, Montauk's downtown, and have access to a pool area.

Great retreat for a long weekend. Enough space for family of four. Easy access to everything in the Greenport area. Mia was very responsive, and the place was great. We would stay here 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.