Waterfront vacation rentals in Shirley

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

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

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.

Eleg B&B Stu Apt steps frm Nautical Mile

-Pvt Studio -Special Occassion Decor -Bkfst: pcakes, waffles, Jimmy Dean -Mr. Cool A/C & Ht Pmp -Fireplace -Recliner/pull-out bed, -Bkfst bar, -Kitchenette -Kurig Mach -Elec Kettle -Mwave -Refrige -Toaster -Jet Blndr -Iron, Iron Bd, hangers, (Hallway closet) -Hair Dryer (Hlwy clst) -WiFi -Wht Noise Mach -PS4, Fire Stick, -Ergo Chr, Dsk, Mse, Mntr, Keybrd -50 Inch smt tv, -Bosch hot water, -5 min walk to Nautical Mile <40min train to Mhttn/JFK -Jones bch -Wstbry Mall -UBS Stadm -Eshr Pk

Gorgeous Waterfront and Indoor Pool Family Oasis!

Breathtaking Waterfront home with 37 foot heated indoor pool. 3 Bedrooms plus a 800 Sq/Ft master bedroom with wood burning fireplace. WiFi, 3rd floor entertainment room with 120 inch screen movie projector, karaoke, fooseball, pool table. Wraparound terrace, sunroom, 45ft dock with launching ramp, putting green, sand trap, outdoor kitchen, bar & stone patio with tables & BBQ grills & fire pit. Ability to catch abundant fish & blue crabs right from the dock. Picture tells a thousand words.

Cozy Country Cottage #2

Relax and get away from it all at this newly renovated cottage in historic Miller Place. Enjoy your private fenced in backyard with your own deck, picnic table and BBQ. You can walk across the street to the historic Miller Place Pond or walk 2 blocks to the famous McNulty's Ice Cream Parlor. Take your beach gear 2 miles to Cedar Beach or go 4.5 miles to Port Jefferson for the best food and entertainment. So many options for dinning and entertainment. You are at the foot of wine country!

Joyful Beach House, viewing The Great South Bay

Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

Quiet Waterfront Entire Apartment

Nestled in South Freeport, this 1 Br apt brings it all within your reach. Whether you are hoping to relax/work while drinking coffee on the patio or living room over looking the water, this is a very quiet and relaxing place to be. 5 minutes from the famous Nautical Mile where you can enjoy different restaurants, boat rides and other activities, minutes away from Southern State and Meadowbrook Pkwy, 15 minutes away from Jones Beach. Near different universities. AC in bedroom as well

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Note our pool and dock are closed and will open Memorial Day Weekend (late May 2026).

Harbor Studio - Across from historic Northport doc

Across the street from historic Northport dock and the beautiful town park, this downtown studio is walking distance to everything. Drive or boat in to town and have a lovely convenient place to stay close to everything. Dining, shopping, the park, and the Famous Engleman theater. The studio has a private entrance, full kitchen, and bath with shower and tub. Enjoy a night, weekend, or whole week in historic Northport Village.

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

Peaceful Classic1920s Milford beach cottage steps from Silver Sands Beach & boardwalk. Blending coastal charm with modern comfort, it’s perfect for vacations, remote work, or longer stays. Walk to downtown shops, restaurants, and train. Ideal for Yale visitors, travel nurses, or weekend getaways. Enjoy a private, pet friendly retreat surrounded by nature yet close to New Haven, NYC, and Connecticut’s best shoreline attractions