Condo vacation rentals in Shelter Island Heights

we had a wonderful weekend staying at the plum! it's located in a great location walkable to town and the beach.

We really enjoyed this spot! We walked to the beach as often as possible and we were able to walk to Teddy's Pizza from the location which was a huge plus with their amazing food! Hosts were very responsive and easy to communicate with!

Had a relaxing weekend in Greenport and absolutely loved this condo. The water views were perfect and it was a short drive into downtown Greenport for excellent restaurants and shopping. Would absolutely stay here again!

Rate was great, it was off season. Cleaning fee is a little nutz considering it is tiny. VERY clean, perfectly functional. I wasn't a fan of the mattress, way too soft for me, but maybe that is just me :-) Overall I would happily stay there again. It was quiet, the other tenants were very friendly.

I thoroughly enjoyed my stay in this functional and comfortable beach community.

We had a great weekend and would definitely recommend this place for a family trip, girls weekend, etc.

This was a wonderful place to stay. Clean and just beautiful. The condo and the scenery. My family and I truly enjoyed our short stay. Only one night. Looking forward to coming again and spending more time

absolutely wonderful experience, very comfortable and clean , Jeff was extremely friendly and helpful , would definitely stay here again and recommend to anyone ! 5 star experience!

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.

This is a great studio. We have stayed in many Airbnb’s past 4 years of coming to New Haven for daughters college years but never in such a good location This is walkable to everything Yale and downtown Soooo many good restaurants plus the museums etc Very Comfy bed lots of towels Shower water takes a minute to get hot but there’s lots of it when it dies plus there’s dispensers of shampoo conditioner and body wash. even iron and board plus umbrellas! Everything u could need has been thought of! Will definitely book again. Hosts very responsive. Some reviews mentioned the elevator …worked fine for us! FYI very clean well managed laundromat next door Thank you

The host was incredibly responsive and helpful. The house was clean, exactly as described, and in a fantastic central location. A great value, exactly what my family was looking for this weekend in New Haven. Highly recommended, easiest 5 stars I've given in awhile.

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+

The space is adorable, and we loved the history of the rental and the community. The location was perfect for us—close to everything and secluded all at the same time. Also Jeff is an amazing host and made us feel welcome/at home. The next time we have to head to NY for a family visit we will definitely try to stay here again.

An impeccable stay, so much so that I’m actually sad to leave. A very convenient location that is a five minute walk from the campus, and anything else is extremely close by. Clear and efficient communication, clean and organized space, will 100% stay again

Great place to stay in Sag Harbor!

Picture perfect! Newly updated accommodations with all the comforts of home. Extremely clean and very well managed. The view from this place is incredible. The perfect oasis in Montauk. Khrisna was extremely responsive and accommodating in our needs. Will definitely be back again!

I had such an amazing stay at Diamondos place! I stayed for three weeks and fell in love with it. Her place is EXACTLY like the photos she provides. She was a very pleasant host and responded very quickly. This place is located in a very nice and quiet condominium community with a pool, tennis courts, and even chairs by the water! My favorite part was sitting on the large patio and watching the sunsets and deer! I would highly recommend this place as it is exactly as the listing.

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.

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

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!

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.

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!