Holiday houses in Shirley

3 bedroom cottage rental

3 bedroom, 1 Bathroom cottage. Fully furnished. Home includes three bedrooms, living room, fenced in yard. Washer/dryer available for use. Wifi and smart televisions. 1 block walk to local beach area and playground, BBQ area. Smith Point Beach: 2 min drive to Smith Point. (1 mile away)The County's Largest Ocean front Park, offers: Swimming, surfing, saltwater fishing, camping, outer beach access, food concession, playground, showers, & special events in season. A short drive away from the Tanger Outlets , Farms, Splish Splash Waterpark, Hampton Bays, Montauk Point, State Park and Long Island wineries. (Please note -2nd and third bedroom is in the attic in case you have small children or those with mobility issues. Stairs are viewable in photos) minimum 2 nights stay 100 cleaning fee All Bills included.

Value · Family · Breakfast

Private Cottage

A large rustic apartment space with lots of windows that open a view to the garden. The place is cozy and comfortable with high ceiling and dark laminate wood floor including full bath with a tub and fully equipped kitchenette. A quiet and private suite with private entrance. Charcoal BBQ-grille, outdoor swing, lots of trees and grass Near beach, Wildlife refuge and hiking paths. A 5-minute drive to a Chinese restaurant and a sushi place, Chipotle, an excellent Chicken hotspot and food markets.

Value · Location · Quiet

Luxurious Waterfront Beach House On The Bay

Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay with private beach... The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the enjoyments the island has at your fingertips. Centrally located to all island destinations. 90 minutes from Manhattan - 15 minutes to West Hampton - 15 minutes to Fire Island Ferrys. Visit top winery’s WiFi

Location · Family · View

Sunset Cottage - Waterfront Getaway

Shirley coastal escape awaits! As you step onto the spacious deck, you'll be greeted by breathtaking views of Bellport Bay and the vast expanse of the Atlantic Ocean, setting the stage for unforgettable sunsets painting the sky in hues of orange and pink. Modern kitchen ready for culinary adventures. Private beach in your backyard and Smith Point Beach a 5-minute drive. Wineries & Hamptons all within 30 mins. Experience Shirley's beauty and serenity and let your vacation dreams come true.

Family · Value · Cleanliness

Home Sweet Home by the Beach

Welcome to your cozy retreat on Eastern Long Island. This charming basement apartment is separated and private from the rest of the home. As you enter the backyard you'll see a small patio with a table and 2 chairs. The apartment has an open-concept living area and kitchenette. Just beyond the living area is a full bathroom and spacious bedroom with a Roku TV. Attractions include Smith Point Beach (5 min), Shopping at Tanger Outlet (15 min) and local restaurants. Easy access to NY-27 & 495.

Value · Location · Access

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

Value · Family · Biking

South Shore Studio

Welcome to your private Mastic studio! This brand-new space is perfect for two adults looking for a quiet getaway. ​Inside, you'll find a queen-size bed, a full bathroom, and a small but fully equipped kitchen with everything you need to prepare meals. ​Step outside to your private outdoor space, featuring a fire pit and comfortable seating—perfect for relaxing after a day of exploring. ​Conveniently located, just a short drive from local shopping and all the best Long Island has to offer.

Value · Family · Pets

Modern Hamptons Home

Escape to a beautifully renovated Hamptons retreat designed for comfort, privacy, and effortless outdoor living. Enjoy a spacious deck and private fenced backyard featuring a unique outdoor lounge, BBQ grill, fire pit, and refreshing outdoor shower. Inside, bright and stylish spaces offer all the comforts of home. Perfect for relaxing, dining outdoors, and creating memorable moments with family and friends, all while being conveniently located near beaches, restaurants, shopping, and local.

Family · Location · Barbecue

Bellport Bay Designer Retreat | Stunning Sunsets

Curated waterfront designer retreat on Bellport Bay with sweeping bay views and light-filled interiors. This elegantly designed 3-bedroom, 1-bath home sleeps 5 and features an open-concept living space, fully equipped kitchen, and refined coastal décor. Step outside to a spacious deck with grill, fire pit, and direct bay access for kayaking and swimming. Just minutes from the beach at Smith Point County Park. Your peaceful coastal getaway for rest, connection, and unforgettable sunsets.

Location · Family · Hospitality

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 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 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

Value · Location · Pool

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.

Family · Location · Cleanliness

Welcome to Bill & Debbies AirBnb

Welcome to our AirBNB. We hope you will enjoy your stay in your private apartment. You will appreciate the off street parking & private entrance. We are only a short drive away from Long Island’s North Fork Vineyards, Skydiving, Smith Point County Beach, Fire Island and much, much more. We are also only 2.5 miles from Brookhaven National Laboratory. Only a short drive from a huge selection of stores & restaurants. We are in easy walking distance to a deli and 7/11.

Location · Family · Nearby