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Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

Ranked #1 AirBNB. Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Paradise Citadel hottub, Htd pool golf basketball

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 🚗 Free Parking 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

Ultimate House with Heated Pool, Hot Tub and Sauna

Ultimate house with 4 Bds, 3 Baths, finished basement with entertainment area and gym. Minutes from the Hamptons and North Fork. Everything for your rest in any weather and season. Yamaha piano, Japanese massage chair, karaoke, drum set, electric guitars, ping pong, fossball and pool tables,board games. Fully landscaped backyard with flowering plants, outdoor lights. 2 BBQ areas, Gazebo with fireplace and projector. Easy access to beaches, restaurants, farms, vineyards and shopping.

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.

Shelter island retreat

Two bedroom on the top floor of a house on Shelter Island on secluded one-acre. fire pit, wood-burning fireplace, layered decks, stainless steel kitchen, five minutes to beach. close to the south ferry .outdoor sauna and hot tub. Own entrance very private. owner lives on property as well in very separate space. 19W-0009 Own entrance very private. owner lives on premise as well in very separate space.has cat that lives in studio with owner 19W-0009 Long term rental also Available

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.

Renovated Hamptons home with a pool and a hot tub

Welcome to our newly renovated 3-bedroom retreat located in the pristine East Quogue community! You're just a 10-minute drive from both ocean and bay beaches. Revel in the great outdoors with a heated saltwater pool, a backyard grill, and a spacious patio and deck for seating and dining. Whether you are planning an elevated weekend getaway with friends and family, or need a change in scenery for your work-from-home lifestyle, this is the perfect home to do both.

Gorgeous House In The Hamptons

A family friendly home that can house 14 people & more. A big house with a pool and hot tub. All year round hot tub, close to ponquogue beach 5-8 minutes away. Restaurants, liquor stores, grocery stores all near the house. 3 minute walk from the house to the bay. Big yard and firepits, the house is private and peaceful. The neighborhood is peaceful and safe. This house is perfect for a family vacation if you want to travel in the hamptons near the beaches.

Hampton's Haven

5 bedroom, 3.5 bath contemporary ranch style home, with custom shaped heated pool and meticulously maintained 7 seater hot tub. Expansive patio w/outdoor dining for 10 - close to beach, town and more! Our home has comfortable office space with gigabit wifi throughout! Fabulous game room with ping pong, 4 person air hockey, smart tv and board game lounge. Everything you'll need for a memorable gathering of friends or the perfect family vacation!