
Condo holiday rentals in Sag Harbor
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Top-rated condo rentals in Sag Harbor
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Popular amenities for Sag Harbor condo rentals
Weekly condo rentals

Water front, sunsets, sail boats, Wi-fi, birds
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!

Beautiful condo on Long Islands Northfolk
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!

Sag Harbor Mona Lisa suite
I cannot say enough good things about Michael's place. He was amazingly responsive and incredibly generous in how well-equipped the space is - everything is luxurious and the fridge is stocked! For as nice as it looks in the photos, it is even larger, brighter and more welcoming in person.

Seaside Summer Escape: 2BR Waterfront Condo w/Pool
We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.

Beautiful Waterview Condo on the North Fork of LI
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!

Waterfront Elevated Bungalow - Spectacular Views
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.

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath
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+

Seaside Summer Escape –2BR Waterfront Condo w/Pool
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!
Condo rentals with a pool

Charming Bayfront Condo
Stop whatever you’re doing in the area and take 10 minutes to walk across the street to enjoy the sunset. I guarantee it’s addictive. Spent a post-Labor Day weekend with some friends and had an amazing time. The condo is centrally located between downtown Southampton, Bridgehampton and Sag Harbor and all that those areas have to offer. Several beaches, both bay-side and ocean-side, are also close by, but we mostly ended up lounging by the pool. The condo itself is spacious which is only further amplified by the amount of natural light reflecting off the bright interiors that let you know you’re near the beach. There are plenty of towels—both bath and beach—and there is ample beach equipment that you can use. The kitchen is fully stocked for cooking/dining at home, and there’s an outdoor patio equipped with a grill and dining furniture. Hostess could not have been nicer or more responsive, so I will definitely want to stay here again.

Bright and Airy One Bedroom Apartment in the Dunes
A fantastic place to stay in the Hamptons, a special gem of a place located in the Dunes of Amagansett, will be back every year!

Cliffside Resort Poolside Condo A106
Very lovely place to stay. All the amenities you would need and a view of the water. With the exception of the keypad entry not working at the end of our stay (assuming it was just dead batteries), it was wonderful.

Seaside Summer Escape –2BR Waterfront Condo w/Pool
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!

Beautiful 2 Bedroom 2 Bathroom Pool-Side Condo
Stay was great and the place was very clean

Step Into the Sand from this Full Service Unit!
This place is excellent. So pristine and pure. One of the last few places on earth so un touched by man.

Two Bedroom Lawn Side 1st Floor Condo!
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

Cliffside Resort Poolside Condo A105
Beautiful stay at Cliffside! The photos don’t do it any justice!! The rooms were super clean and well decorated. Pool was great!! The beach was beautiful!!!! Loved this place!
Private condo rentals

Cliffside Resort Poolside Condo A101
Really liked the place but our reservation didn’t end up getting entered into the Cliffside system - so I had to call the after hours emergency service to get the code to get in. Not a huge deal but a little scary,

Sun Drenched Loft-City Living in the Country
This place is great in old-school AirBnB style. Feels like Nadine’s second home being shared with us. Quality finishes throughout, very well stocked in terms of glasses, plates, towels, etc. We came for a wedding but were able to have our own nuclear family reunion with three young-adult children coming in from around the country. The space handled us all with ease. The great room is spacious with a big table and even bigger sectional sofa. Just a great place to gather and hang out (which we did a little more than expected because of tropical storm Ophelia). We enjoyed the coffee and sandwiches across the street and brought in sushi and wine for one dinner, less than 5 minutes drive away. One quick note: 2 BRs not 3

Cliffside Resort I Water View 2 Bed Condo

Cliffside Resort Poolside Condo A205

Two Bed Corner Condo I Incredible Sea views!

Seaside Escape I The Cliffside Resort Exclusive
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- Beach
- Charlestown Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- Shinnecock Hills Golf Club
- Walnut Public Beach
- TPC River Highlands
- Ocean Beach Park
- Woodmont Beach
- Amagansett Beach
- Blue Shutters Beach
- Seaside Beach
- Silver Sands Beach
- Quotonset Beach
- Heckscher State Park
- Ninigret Beach
- Outer Beach at Smith Point County Park
- Groton Long Point South Beach
- Connetquot River State Park Preserve
- Wildemere Beach
- Cedar Beach