Smoking-friendly holiday rentals in Suffolk County

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 my 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 .

The Easy Stay Southampton

You will be close to everything when you stay at this centrally-located place very quiet , very romantic also for a nice getaway weekend , feel free to enjoy this cozy place Are you looking for comfort, style and good location in Southampton? Discover The Easy Stay: your ideal space to relax, work or explore the city. Perfect for travelers, couples, students or passing professionals. •Modern studio •Easy check-in •Quiet area •Amazing pool •Just minutes from the center and the statio

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 | 1- Night Stays 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!

“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.

Pet Friendly One Bedroom House

Great pet friendly house located close to the water, downtown, beaches, train service and I-95. Off street parking, laundry facilities, great fully fenced in back yard. Large, one bedroom and one bath with a pull out queen size sleeper couch in the main room. Wi-Fi, Roku TV, boards games, and DVDs available. Property is located close to restaurants and many outdoor activities including the town beach and docks. There is a pass available to bring a car to the Clinton town beach.

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.

Chic Hamptons Retreat w/ Pool

Escape to this beautifully designed Hamptons retreat, where indoor and outdoor living blend seamlessly. This private oasis features 2 bedrooms, a pool (not heated) with a spacious oak deck, a firepit, and an outdoor dining area. Enjoy a BBQ grill or the outdoor shower, and there is card access to a private beach. Luxurious French Presse linens and decor elevate your stay. Just minutes from stunning beaches. Ideal for small families or couples seeking a refined, relaxing getaway.

4BDM close to East & Sag Villages-Pool+ FirePit

Enjoy summer by the heated pool and the outdoor patio, large fire pit, and BBQ, perfect for year-round gatherings, grilling. Cozy up by the fireplace in the living room for a relaxing stay. The house also includes two spring floor mattresses to accommodate larger groups. POOL reopens 5/2026. House is close to town beaches and villages, just 5 min to Sag Harbor, 8 min to East Hampton Village, and 15 min to Wölffer Vineyard. Pets are welcome. Home is equipped with 1GB Wifi.

The Sea Shack

Welcome to our home, ideally situated just minutes from the heart of town and a short 10-minute drive to the best surfing beaches in the Hamptons. 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!

Chic Hamptons Retreat | Fireplace, Hot Tub, Beach

Stylish & airy Hamptons retreat on over an acre, 5 min to ocean beaches and Westhampton Village. Thoughtfully designed, this home features 4 bedrooms, 3 full baths, and a modern open layout across 2 floors. Outside, a hot tub and fenced yard offer space to unwind in privacy. Clean design, abundant natural light, seamless indoor-outdoor flow, and a calm vibe make this home ideal for an escape. Enjoy peaceful mornings, beach walks, and cozy nights by the fireplace.