Smoking friendly holiday rentals in Fire Island

Walkable Vintage Village Apartment

2 bedroom upstairs apartment just a short walk to the train station, beach and town (1 mile to all 3). Location wise this is as good as it gets especially if you have no car. Please keep in mind this house is over 100 years old and it has its quirks. This is not the 4 Seasons! This is my primary residence when not rented so some of our personal things are there. No pets. I am allergic. Even “hypoallergenic dogs”. Parking on street only. Parking for one car maximum. Not suitable for toddlers .

Modern home with pool near beach

Our home is located in Shirley, Long Island. It is two miles away from oceanfront Smith Point Beach. This listing is to book the entire home when we are out of town. Please check our reviews on the other listing of the same room and home. The guest bedroom is on the main level of our home, with a bathroom adjacent to the room. The room is equipped with a comfortable queen size bed, table with two chairs, closet, two nightstands, an armchair, and Apple TV with various streaming apps to use

Spacious Retreat w/Jacuzzis -1- Night Stay Welcome

* We are open for One Night Stays-please message for price$ Escape to this beautiful home on 3 private acres close to West Hills County Park. Enjoy the best of both worlds—serene outdoor adventures just minutes from the Walt Whitman Mall and top shopping spots. Designed for entertainment and family gatherings, this home boasts a stunning kitchen, luxurious bathrooms, and two relaxing hot tubs. Whatever your pleasure, this is the perfect getaway for nature lovers and city explorers alike!

"Backyard BBQ, Beats, Hot Tub Retreat”

Simple, stylish home is perfect for the artsy types - small families, weekenders, traveling business executives, golfers and creatives are welcomed. Features five beds (sleeps 6) and two baths, comfy living room, dining room and office den. Spacious patio and large back yard for relaxing. Enjoy the hot tub, fire pit and BBQ…Drop in the Soho vibe basement for great music. Surrounded by 4 major colleges. Additional $100 fee per guest per day for parties/events (20guest max) . No exceptions.

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. $19 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.

The Design Studio Suite | 2 Beds | Spacious | Luxe

Private one bedroom apartment with modern decor offers everything you need for a short or long term stay. Space includes a full kitchen separate from studio area, & washer + dryer. Studio offers a Queen Sized bed, pull-out bed, workspace, 70 inch Roku Smart TV & hand painted artwork. The Location Less than two miles from Merritt Parkway, near I-95 & East Norwalk train station. One mile away from large shopping center and less than half a mile away from local convenience center.

Cozy tiny log cabin on 13 acres

Tiny rustic cabin located in the woods. Large screen TV and Wi-Fi. No stove but will provide cooktop and toaster. Full bathroom with shower. People love the back deck to enjoy their morning coffee and to watch for wildlife. One bedroom with comfy queen bed and fan. All linens and towels supplied. Please be aware this is a rustic beautiful site. Trails in the back and very close to rail trail. Mini splits will keep you toasty warm in the winter and ice cold in the summer.

The Sea Shack

Welcome to our home, ideally situated just minutes from the heart of town and a short 10-minute drive to beaches, restaurants and the US OPEN. This charming home offers the perfect blend of privacy and convenience, making it an ideal retreat for anyone seeking a serene escape. Whether you’re looking to relax in a peaceful setting or explore the hamlets, our home offers the best of both worlds. Book your stay with us and experience the perfect Hamptons getaway!

Charming Apt in the Heart of the Hamptons

Welcoming studio apartment with queen bed, living room and spacious full bathroom. Kitchenette complete with laundry. Small deck with delightful creek-side views. And this unit includes cable TV and Wi-Fi. Please note that there is an extra fee of $75. per stay for each pet, There is a queen sofa bed in living area for quests at $75 additional fee. This unit is attached to the main house.

North Fork Waterfront Escape · Sunset Views

Enjoy spectacular views of Hashamomuck Inlet off Shelter Bay from the living room, kitchen, deck, garden, and private dock of this newly renovated 3-bedroom home. With 90 feet of waterfront and a small sandy beach, it's ideal for kayaking, clamming, and swimming — perfect for families with young children. Relax with sunsets, barbecues, and local North Fork wine. The perfect family getaway!