Holiday rentals in Middle Island

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Middle Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Cabin in Rocky Point
4.88 out of 5 average rating, 575 reviews

Little, cozy place near beach for a couple.

It's quiet and cozy here. The yard is completely fenced with tall living shrubs, flowers, and trees. There's a gas grill, a fire pit, and a place to dine under an umbrella in the garden. I rent out a separate half of the house to guests: one bedroom, a small kitchen combined with a hallway. Peace and quiet reign here. You won't be disturbed. Sometimes I go into my half of the house, but very rarely. There are no other guests on the property, just you. I don't charge extra for pets. Parking free.

Guest favourite
A light-filled bedroom features a spacious bed with striped linens, situated next to a cozy sofa. A flat-screen TV is mounted on the wall opposite the bed. A large window allows natural light, with sheer curtains enhancing the bright ambiance.
Flat in Coram
4.93 out of 5 average rating, 245 reviews

Private King Suite in Quiet, Cozy Setting

Separate apartment with private keyless entrance. Cozy one bedroom king suite and sofa with full pull out bed. Full kitchen and dining area. Bathroom with standing shower. Free parking on premise for up to 2 cars. Quiet, family friendly neighborhood. Located in the heart of Long Island. Close to everything! Wineries, Farms, breweries, golf, shopping, great dining. NYC is a only a train ride away! Conveniently located within a mile of groceries and laundromat. High speed WiFi, 55in smart tv

Guest favourite
A well-maintained garden area features colorful flower beds along a gravel pathway. Lush green grass stretches out in a spacious yard, with trees and shrubbery framing the property. A decorative lawn feature is visible, enhancing the inviting outdoor space.
Guest house in Middle Island
4.97 out of 5 average rating, 36 reviews

Private newly renovated apt

Newly renovated private apt. 20min to Port Jefferson, Ceder Beach, Smith point. About 30-40 min from the Hamptons bays and 45 min from south hamptons. 1 mile from Walmart. private end of the street home. Property is on 1.5 arch .1 bed room l- a queen size bed and 1 full bath. Funton for extra guest. Heated floors for the winter. 25min from Ronkonkoma train station to ride into the city in an 1 hour and 20 to Penn station. *This property is exempt from receiving service pets** not pets allowed.

Guest favourite
Home in Centereach
4.98 out of 5 average rating, 61 reviews

Cozy Modern Getaway

Cozy Modern Getaway in Centereach! Perfect for students, medical visitors, and travelers. Relax in a bright living area with 55” Smart TV+PS5, dine at a 2-seat nook, and cook in the well-equipped kitchen with refrigerator, microwave, coffee maker, popcorn machine, cookware, dishes, glassware and more. Bedroom with fresh linens, (queen size bed), clean bathroom, fast Wi-Fi 300 , AC/heat, and free parking. Close to Stony Brook Univ 13 min, Port Jefferson Hospital 15 min, and Suffolk College 5 min

Superhost
A well-maintained yard is filled with vibrant green grass and neatly trimmed shrubs. Several ornamental trees and white statues are positioned throughout the landscaped area, providing a serene outdoor setting. A suburban home with light-colored siding is visible in the background.
Flat in Centereach
4.87 out of 5 average rating, 75 reviews

Casa La Detente Fall Vacation Getaway

Casa La Detente is a 1 Bedroom apartment in a Private Family House. Centrally-located in Suffolk County in the Suburb Heart of Long Island. It has a Separate Entrance and Private 1 Bedroom,2 Queen Size Beds, Living Room, Full Size kitchen, Washer and Dryer, DeckBackyard, Fire Pit, Plenty of Parking Space. It is near Winery, Casino, University, Supermarket, Mall, Shopping Center, Bars and Restaurants .Two 70 Inches Smart TV, Keurig Combo Coffee Maker,Tea Kettle and too many more to be listed.

Superhost
A spacious living area features large glass windows that frame a stunning sunset over the water. The open design enhances natural light, illuminating the room's elegant furnishings and wooden accents. A dining table is positioned near the windows, inviting relaxed meals with a view.
Cabin in Shirley
4.83 out of 5 average rating, 204 reviews

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.

Superhost
A spacious outdoor pool is featured, surrounded by lush greenery and colorful landscaping. The pool's clear waters reflect the sunlight, and gentle waterfalls create a soothing ambiance. A textured stone deck frames the pool, providing ample space for relaxation.
Holiday home in Miller Place
4.81 out of 5 average rating, 32 reviews

THE MULBERRY OASIS

Bring your family to the custom luxurious mansion on Long Island carefully curated furnishings. No need to lift a finger - wonderfully comfortable and professionally decorated spaces are ready for you to enjoy. Many bespoke items such as a large crystal entry chandelier- custom living room furniture that add unique character and charm. Amazing entertainer's kitchen with gray cabinet. A premier basement with amazing entertainer's, pool table, game table, theater room, exercise /sauna room.

Top guest favourite
A well-appointed sleeping area features a queen bed with crisp white linens, flanked by two illuminated nightstands. Above the bed, an abstract art piece adds a pop of color to the neutral walls. A small plant is positioned near the bed, enhancing the calming atmosphere.
Place to stay in Coram
4.99 out of 5 average rating, 138 reviews

T&T Unique Space

NEW ! Private renovated studio attached to a single family home. Private entrance queen bed w/full bathroom, sofa, 55”smartTV, kitchenette(no stove)free street parking in front of house.This is a drug free, non-smoking, no pets and no party unit. Minutes from Port Jefferson pier, LIRR, Connecticut Ferry, 15 min. to Mac Arthur airport. Shopping in Riverhead at Tanger Outlets a few exits from the LIE. 10min. to John T Mather Hospital & St Charles Hosp. Near Jakes 58 Casino and Top Golf.

Guest favourite
The exterior features a charming facade with wooden shingles and a welcoming front porch. Two vibrant blue doors highlight the entrance, surrounded by blooming flower pots and neatly arranged greenery. White columns support the porch roof, enhancing the spacious feel of the entryway.
Home in Port Jefferson
4.91 out of 5 average rating, 204 reviews

Harborfront Star Walk to Harbor & Village

Leave your car parked , hang your keys, and step into the charm of Port Jefferson Village from this beautifully styled coastal retreat. Perfectly located just steps from the waterfront, placing you within easy walking distance of the marina, Harborfront Park, boutique shops, cafés, restaurants, and the ferry. Whether you’re here for a relaxing getaway, visiting Stony Brook, or exploring Long Island’s North Shore, this home offers the perfect blend of comfort, style, and location.

Superhost
Home in Middle Island
4.6 out of 5 average rating, 35 reviews

Private 2 bedroom basement w/ private entrance

Newly renovated, very clean, quiet, private basement apartment setup. Tv in living room and sperate TVs in each room with all streaming services (must use own log in) 1 King size bed 1 Queen size bed Only entire basement available. Reservation must be made by the person or persons staying in the listing. Booking for other people (Third party booking) is not allowed. NO visitors allowed inside listing. NO extra guests (unless it was booked that way) *HMO taxes applied*

Guest favourite
A cozy bedroom features a spacious bed layered with soft bedding and decorative pillows. Pendant lights hang on either side, illuminating the room. Simple wall art and round mirrors add visual interest to the neutral walls, while natural light filters through a sheer curtain.
Flat in Medford
4.8 out of 5 average rating, 112 reviews

Blue apartment in Long Island, Ny

Welcome to our blue apartment a Peaceful, comfy one bedroom apartment suitable for 4 people. Private bedroom has a Queen size bed with comfy mattress and two small closets to keep your belongs. Living room has two twin comfy beds, tv and desk. Kitchenette is equipped with necessities for a quick meal and coffee maker. You can also enjoy the shared backyard with the fire pit. Keep in mind if you stay past our check out time you will be charge an extra night.

Superhost
Home in Farmingville
4.75 out of 5 average rating, 20 reviews

Your ideal getaway awaits !

Welcome Kick back and relax in this calm, stylish space ! If you're looking for a comfortable, cozy, and perfectly located place to explore the best of the area, this is your ideal choice. Our property is located right in the center. Our home for unforgettable family gatherings. With 3 bedrooms, 2.5 bathrooms, and 4 beds, with pull-out couch. Our home ensures comfort for large groups. The fully equipped large kitchen invites memorable meals together.

Popular amenities for Middle Island holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Suffolk County
  5. Middle Island