Condo holiday rentals in Fire Island

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.

This unit is part of a resort so if you book this, contact them directly via phone to manage the reservation vs relying on Airbnb. That said, everything was seamless once we got to the resort. We arrived earlier than the check-in time, but the front desk allowed us to access the unit. It was well-appointed, we had everything we needed for a comfortable stay. The pictures may not show it, but it is a compact 3-bedroom unit - the bedrooms/bathrooms run smaller than the average but are sufficient to fit 7 people. The living room though is very spacious and you also have a sweeping wraparound deck that gives you great views of the beach, with ample deck chairs and umbrellas for lounging. The best part is that it literally is a stone's throw away from the beach, and there's an attendant that will provide beach towels, umbrellas and chairs. Parking in front of the unit is limited, so you may have to walk further to get to the big parking lot (the unit is on the edge of the resort).

Thank you for allowing us to stay at your rental. Very convenient location, very neat, and modern. Love the slider door to the one bedroom. We were informed about the long term renter on the second floor in the description, however the upstairs tenant was very active in the early hours (1am, 3am) and we were woken up each night by the sounds of heavy walking, tv, and conversation. It was not all night in duration though. Overall, it didn’t dampen our stay at the rental but if someone has a baby or toddler, they may have an issue with the sound from above.

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!!

Hassle free check in. Space is clutter free, clean and quiet. Plenty of free parking on the block. Walking distance to a deli, subway and other small businesses. Vincent is a quick responder and was super accommodating for a small request I had asked of him. Check out was also hassle free. All in all I would give this a 10/10!

Stay was great and the place was very clean

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

Daniela's place was conveniently located for us to go to our family events. The condo was incredibly clean!! Absolutely spotless!! I would recommend staying here without a doubt!

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!!

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.

Finn's place is a great base for exploring New York. We enjoyed being able to escape the busyness of Manhattan and retreat to the apartment. It's really easy to get around and all the local recommendations were great too. We especially liked left hand path and the honeymoon cafe - especially if you need an English breakfast tea in the morning! I would highly recommend. Great location, and great views from the apartment!

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

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+

I thoroughly enjoyed the condo! It was well within walking distance to downtown, and the building staff was friendly. Would stay here again.

Excellent place to stay! This was my second visit, and once again, I had a wonderful experience. The room in the upper floor is the best as you avoid unwanted noises (traffic, other people walking). They are also implementing a new system for the washer/dryer that allows you to pay with your cellphone, making it much easier to pay now. They are usually quick to answer and helpful. I recommend this place for sure.

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

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.

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.