Smoking friendly vacation rentals in Fire Island

3br + game rm abt 45min drive or easy train to NYC

This cozy 3-bedroom Port Chester house (accommodates up to 11 people), offers excellent value, spacious living, and proximity to NYC and Greenwich, CT. A short 10-min walk brings you to the center, the historic Capitol Theatre, & the train to NYC. It's a quick drive to key landmarks and attractions, about 40 mins to NYC, with a train ride to Grand Central taking 45-60 mins. 11-min walk to Capitol Theatre. Perfect for those seeking a quiet, safe neighborhood close to the vibrant city centers.

Harbor Water Views

Situated just one house away from the picturesque Great South Bay on a quiet cul-de-sac, this rare gem in an American Venice setting boasts southern exposure and underwent updates in 2019. This charming residence is a 2-bedroom, 1-bathroom Classic Cape featuring a generously sized deck that was revamped in 2021. Conveniently located minutes away from shopping, beaches, and parks, this home provides a secluded retreat from the hustle and bustle, offering tranquility away from traffic and noise.

"New and spacious Luxury RV home in Vibrant Town.”

Welcome. Step into our beautiful RV where every detail has been designed for your enjoyment. Our RV is fully equipped with everything you need for a relaxing stay, including complimentary water bottles, and fast WiFi. Located just 30 miles from NYC, our RV offers the perfect blend of convenience and relaxation. When you're ready to unwind, retreat to your private oasis complete with electricity and water. Park your vehicle in your designated parking spot and enjoy a hassle-free stay.

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath

Discover the “Cool House” This is the coolest waterfront getaway on the south shore of Long Island! Waking up to beautiful sunrises, dinners with a sunset every night & dancing under the stars is a lifestyle your family & friends will cherish forever. The perfect escape from NYC, minutes from the Atlantic Ocean & just a short drive to the Hamptons! This meticulously renovated oasis is the perfect living & entertaining space, a trendy retro beach vibe designed for fun or relaxation.

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy

Welcome to Coast to Coast - the perfect getaway from NYC! You may have heard about our new little secret - but you’ll have to come see it for yourself to believe it! Step back into prohibition era Long Island in our hidden speakeasy! Right by Smith Point Beach, we provide accommodations that go above and beyond- this is not your average AirBnB! Soak up the sun at one of LI's top beaches, then enjoy complimentary Netflix, Hulu, cable and more while you shoot pool or play games.

Her tiny Parisian boat house

Solo vacation? Reconnect with nature at this unforgettable escape. Or a Perfect work space while lounging by the pool…(in SEASON) this tiny house (on land) has access to an outdoor shower and outdoor soaking tub. Wanna relax? Come Meditate under the giant willow, swing in the hammock or practice yoga. Bathroom is shared and just steps inside the main house with shower and toilet. Great WiFi, front porch to enjoy your morning coffee. Bed is a comfytwin with lots of pillows.

GOOD VIBEZ HOUSE! Heated Pool~Hot Tub~GameRm~Golf!

STAY. SOMEWHERE. DIFFERENT. This isn’t just a stay—it’s an experience. Welcome to THE GOOD VIBEZ HOUSE, your private escape in the heart of Long Island. Nestled in a SAFE, QUIET neighborhood, this one-of-a-kind spot blends smart home comfort with tropical resort vibes. From the moment you arrive, it feels like vacation. As Superhosts, we go beyond hosting to deliver a true vibe—with warm hospitality, thoughtful touches, and a five-star atmosphere you won’t forget.

Romantic Camper Getaway: Nature and Charm

Experience an unforgettable romantic getaway surrounded by nature Let yourself be captivated by an enchanting setting designed to awaken emotions and create unique memories. This space, located in the city of West Haven, offers much more than a stay: it's an intimate and special experience, ideal for disconnecting and enjoying as a couple. Discover the perfect place to relax, reconnect, and experience moments that will remain in your memory forever.