Holiday rentals with a hot tub in Southold

A fenced-in slice of Hamptons heaven where both dogs and humans roamed free and happy. It’s basically a resort if your resort includes wagging tails, wine within walking distance, and a private mini movie theater for when socializing gets… exhausting. Days were spent by pool , nights were hot tub therapy. 10/10 would trade city stress for this fenced paradise again.

we had a really great stay at this beautiful house. garden and pool/hot tub are sublime. wonderful location v responsive, helpful, gracious hosts. hope to return

We had an event nearby and Brian’s place was a great base for us. Lovely and peaceful neighborhood. Brian was super responsive and reached out to us when the house was ready(before the official check-in time). Would def recommend to anyone!

We had an amazing stay at Marla’s place in Hampton Bays! The house is beautiful, incredibly comfortable, and in a perfect, walkable location—just a short stroll to a little beach and great spots like Rumba and Cowfish. The backyard was a highlight—absolutely perfect for hanging out with friends and made for some great photos. The jacuzzi was such a nice touch, and the house had plenty of towels, super comfy beds, and great parking, which made everything even more convenient. Marla was a fantastic host—so responsive, kind, and communicative. One small heads-up: there’s no iron or steamer on-site, bring your own if you need a press, other wise you can throw stuff in the dryer for a quick wrinkle release! We couldn’t have picked a better place for our stay and would absolutely love to come back. Highly recommend!

The house is beautifully nestled on a quiet street. We spent five days at the house and very much enjoyed our time there. James was quite responsive to several questions that we had.

This was one of the most thoughtful airbnb experiences I have ever had. The attention to detail was extraordinary. Cindy provided everything you could need -- a perfectly stocked kitchen, umbrellas, sunscreen, bug spray, first aid, yard games, pool floats etc. The house was just as charming -- if not more charming -- than the pictures. Super private but also great location with proximity to a CVS, grocery store and main street in East Hampton. Cindy was also very communicative and laid everything out super clearly with great recommendations etc. We are already planning our next trip!

I had the most amazing stay at this Airbnb beach house. The views were absolutely immaculate, turning every moment into a picture perfect scene. The property was not only impeccably clean but also radiated a sense of peacefulness that immediately helped me disconnect from the hustle of daily life. Every detail was thoughtfully curated from the comfortable bedding that guaranteed a night of uninterrupted sleep to the high quality toiletries that added a touch of luxury to my routine. The well-equipped kitchen made it easy to prepare meals whenever I wished, and the fast WiFi ensured that I could seamlessly blend work and leisure as needed. A true highlight was the friendly welcome with a customized snack basket that set a warm, personal tone right from the start. Additional amenities, such as a cozy fireplace perfect for evening gatherings, stylish decor that elevated the overall ambiance, and easy access to local attractions, truly made my stay unforgettable. I will be returning.

We enjoyed a lovely stay in the beautiful home. Josh was easy to reach and flexible with our requests.

This home was beautiful and exactly as described. The hostess was wonderful and very responsive. The location in east hampton in a quiet and peaceful street was close to all our favorite restaurants, shops and beaches. The hot tub was so great to have in the cold and rainy days. The home is chic, comfortable and clean. We loved it and recommend it.

We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.

We had such a wonderful stay at Ann Marie’s Airbnb! From the moment we booked, she was incredibly kind and responsive, making everything so easy and welcoming. The house itself was spotless, beautifully maintained, and had every amenity we could possibly need — it truly felt like a home away from home. The location was perfect — close enough to town that everything was easily accessible, but just far enough out that we avoided all of the typical Hamptons traffic. We even walked around the neighborhood every morning! We couldn’t have asked for a better balance of convenience and tranquility. Highly recommend this stay, as someone who frequents the hamptons — we’d come back in a heartbeat!

We all loved our stay at Treetops! The pictures really cannot capture how beautifully unique this place is. The pool is lovely. The location is serene and private, yet close to many great restaurants and beaches. Dan was extremely friendly and accommodating. I recommend this place to anyone with eclectic taste looking for a peaceful getaway!