Vacation rentals in Shirley

4.94 out of 5 average rating, 114 reviews

A spacious outdoor dining area features a large wooden table surrounded by matching chairs. Sunlight illuminates the area, showcasing a well-maintained yard with a manicured hedge and a small garden shed visible in the background.

Home in Northport

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

4.85 out of 5 average rating, 133 reviews

A cozy living area features a large sectional sofa with decorative cushions, complemented by a plush armchair. Natural light is invited through two front windows, while a coffee table sits at the center, surrounded by green plants and framed art on the walls.

Home in Baldwin

Clarissa's Paradise

RESERVE NOW: This ideally located five-bedroom totally renovated home is the perfect spot for a family fun vacation. Located within walking distance of the well known playground and spray ground. The home features a spacious patio, central air conditioning, baseboard heating, WiFi, and Cable tv. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. 4 full bathrooms . Sleeps 10. PLEASE NO PARTIES ARE STRICKLY PROHIBITED

5 out of 5 average rating, 43 reviews

A wooden boardwalk leads toward the beach and ocean, bordered by vibrant umbrellas and beachgoers enjoying the sun. The clear blue sky reflects over the water, creating a serene coastal view. The structure allows for easy access to sandy shores.

Home in Ocean Beach

Sunny Spacious Pet Friendly Steps from the Beach

This ideally located four-bedroom home is the perfect spot for your family's vacation. The home features a spacious deck, central air conditioning, WiFi, 4 Smart TV's, a Sonos sound system and YouTube TV. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. There are 2 full bathrooms as well as an outdoor shower. Fully equipped including beach chairs, towels, 5 bikes, 2 wagons and beach toys for the kids. Sleeps 10.

4.94 out of 5 average rating, 108 reviews

An open kitchen space features modern appliances, including a stainless steel stove and ample counter space. Barstools are positioned at a breakfast bar, while natural light illuminates the area through several windows. Warm wood flooring complements the neutral-colored walls.

Home in North Fork

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

4.88 out of 5 average rating, 102 reviews

A covered outdoor seating area is furnished with a combination of turquoise and brown seating, complemented by decorative pillows. Soft lighting from string lights enhances the space. A swing seat is positioned against the wall, and a small table is centered on the tiled patio.

Home in Mastic

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

5 out of 5 average rating, 11 reviews

A view of the Peconic River is depicted from a wooden deck, featuring a small round table and two woven chairs. The water reflects clear blue skies, with boats visible in the distance and trees lining the shore.

Houseboat in North Fork

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

4.82 out of 5 average rating, 67 reviews

A sandy beach stretches out under a clear blue sky, with gentle waves lapping at the shore. Beach grass and wooden fencing line the path leading to the water, where a lifeguard stand is positioned for safety.

Home in Hampton Bays

Spacious Hamptons Oasis | Perfect for Families

Escape to our stunning year-round retreat in Hampton Bays' Red Creek area. With over an acre of lush land, our charming residence offers unparalleled serenity and tranquility just minutes from local bay, beaches, and wineries. Ideal for family fun, friend retreats, and exquisite dining in the Hamptons. For off-season activities, explore wineries, animal feeding farms, apple and pumpkin picking, breweries, and more. Book now for your dream getaway!

4.9 out of 5 average rating, 115 reviews

An outdoor deck area is seen featuring a large round table surrounded by several comfortable chairs. A sun umbrella provides shade, while a propane grill is positioned nearby. Lush trees create a natural backdrop, enhancing the serene atmosphere of the space.

Home in Shelter Island

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

4.98 out of 5 average rating, 179 reviews

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

Home in North Fork

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Cottage in Shelter Island

A traditional New England house is set in the central village of the island, surrounded by lush green lawn. Tall trees provide shade, and the late afternoon sun creates elongated shadows across the grass, highlighting the inviting outdoor space.

4.96 out of 5 average rating, 105 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

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What guests are saying

Sunset Ranch

5 out of 5 average rating, 10 reviews6 months ago

Loved Kenneth’s house. Perfect for my wife & I to get away and explore the north fork for a weekend. Great location Private house Clean Comfy Walkable to Kenneys beautiful beach sunset Drivable/uberable to key winery or Greenport locations if needed Exactly what we were looking for as a mini couples getaway Would highly recommend; likely a returning customer Kenneth was responsive and pleasant with clear instruction 5 stars!

Home in North Fork

What guests are saying

Stylish Beach Getaway: pool & walking location

5 out of 5 average rating, 9 reviews6 months ago

Maher’s house was an amazing peaceful experience. I enjoyed my time there and he had great recommendations to restaurants and activities! He was very responsive with all questions we had. I will totally stay here in the future if I can get the chance again!! Thank you Maher!!

Home in North Fork

What guests are saying

The Sandy Shack - Coastal Escape

4.9 out of 5 average rating, 21 reviews6 days ago

As a native long islander I enjoy finding great properties I can bring my family to to take advantage of all long island has to offer. This was the DREAMIEST beach bungalow!! The bedroom with the two beds was just my favorite room especially since we visited off season. You cannot beat this location. I can't wait to book again during high season! Thanks for sharing your home with us !!

Home in North Fork

What guests are saying

Private Beach access along the Wine Trail

4.92 out of 5 average rating, 12 reviews1 month ago

I would highly recommend Melissa's place in Jamesport. It was a great location with room to enjoy with some family members including children. It was perfect with some toys and a big outdoor area (and a private beach!) for us all to spend some time together while visiting family in the area. Melissa was accommodating and clear in her directions and gave us a warm welcome with a greeting basket, information about the area and coffee! The location is lovely and everything about the house was fun and comfortable. Thanks!

Home in North Fork

What guests are saying

2 Bedroom Hamptons Waterfront Cottage Rental

5 out of 5 average rating, 21 reviews9 months ago

A quaint cottage that was sparkling clean. Access to the Peconic from a private dock with the available kayaks and canoes. There is a pristine built-in pool with new decking. There was a 10 minute drive to Hampton Bays town with great restaurants, grocery and shopping.

Guesthouse in Hampton Bays

What guests are saying

Sunny apt in the treetops of Greenport village

4.7 out of 5 average rating, 10 reviews32 months ago

We loved our stay at Meg’s The house is an older home that is beautifully renovated. Nice older touches on a completely new space. The space was immaculately clean. We loved being close to the hub of town, but not on the Main Street We basically parked our car and didn’t need to drive to get a cup of coffee or for dinner. Check in and out was super easy. Didn’t need to communicate with Meg because everything was in order. She even gave us later check out. Would definitely stay again

Apartment in North Fork

What guests are saying

Newly built twin beach house within steps to beach

5 out of 5 average rating, 8 reviews8 months ago

We stayed here for a wedding at The Burr Mansion, which was extremely close to the house! The house was clean and updated. A few spots to walk to including a local bar. Just a walk to the beach. Bedrooms are all spacious and were very clean. Would definitely stay again.

Home in Fairfield

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Popular amenities for Shirley vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Shirley's top sights

Painters'34 locals recommend

Long Island Skydiving Center27 locals recommend

Mama Lisa Restaurant25 locals recommend

Wertheim National Wildlife Refuge23 locals recommend

Tiki Joe's Smith Point21 locals recommend

Stop & Shop20 locals recommend

Other great vacation rentals in Shirley

Apartment in Downtown Stamford

An expansive outdoor area showcases a heated pool surrounded by wooden decking. Sun loungers and umbrellas are arranged around the pool, with colorful seating accents visible. Pathways meander through lush greenery, integrating seating and recreational spaces within the tranquil courtyard.

4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

4.87 out of 5 average rating, 153 reviews

Large windows allow natural light to fill the open living space, showcasing the stunning view of the Great South Bay. A comfortable sofa with decorative pillows faces the water, complemented by a dining area nearby. Warm wood tones enhance the cozy atmosphere of the room.

Cabin in Shirley

A-Frame cabin with private beach & epic sunsets

5 out of 5 average rating, 13 reviews

Cottage in North Fork

Lovely North Fork Beach Cottage (2 BR/2 bath)!

4.94 out of 5 average rating, 67 reviews

The spacious kitchenette features modern appliances, including a refrigerator and a stove, set against rustic wooden beams and a brick fireplace. Natural light filters through the wooden windows, illuminating the inviting wood flooring and enhancing the open layout.

Cottage in Norwalk

Seaside Serenity: 2B 1B, Patio,Near Beach

4.84 out of 5 average rating, 32 reviews

A modern kitchen is equipped with stainless steel appliances, including a refrigerator and an oven. Gray cabinetry contrasts with a mosaic backsplash. A sink is positioned beneath a window, while a clean mat lies on the floor near the countertop.

Apartment in Brentwood

Home away your home

5 out of 5 average rating, 9 reviews

A waterfront balcony is featured, showcasing wood paneling and a clear view of the water. The deck is equipped with a railing and lights, offering a relaxing spot to enjoy the scenery. The sunlight casts shadows along the planks, highlighting the serene environment.

Home in North Fork

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

5 out of 5 average rating, 24 reviews

A large outdoor pool is surrounded by a stone patio, equipped with several lounge chairs. Lush greenery lines the perimeter, providing a natural backdrop. Soft sunlight reflects off the water, enhancing the inviting atmosphere of the spacious area.

Home in Dix Hills

Nice getaway with your family.