Vacation rentals in Middle Island

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Middle Island

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

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Guest favorite

Apartment in Medford

4.87 out of 5 average rating, 143 reviews

Cozy Apartment with King Bed - Separate Entrance

Enjoy your stay in this private, clean and comfy environment. Space offers a bedroom with a king size bed and a desk for at-home work. Living room includes a smart TV and a sectional. Unleash your inner chef! Access to kitchen utensils, dinnerware, and pots/pans. Free parking on premises. Convenient location with many necessities nearby (mall/gas station/restaurants). We are located 2 mins from I-495 and 15 mins from Macarthur airport. Great for visiting family in Port Jefferson, Patchogue, etc!

Guest favorite

Apartment in Coram

4.92 out of 5 average rating, 205 reviews

Private Apartment- close to shops, Pt. Jeff., SBU

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 favorite

Guesthouse in Middle Island

4.94 out of 5 average rating, 16 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 favorite

Apartment in Mastic

5 out of 5 average rating, 12 reviews

1 Bed room Apartment in Manorville.

Relax with the whole family or friends at this 1 bed room apartment. It’s cozy, well lit, spacious and quiet. Owner’s family live upstairs. Minutes away from the beach or other good restaurants and other touristy locations, 1 hr train ride away from NYC. Beds- 1 Queen bed in bedroom, a double air mattress, and a full size couch. Kitchen has no conventional oven, equipped with electric stove, Air fryer, and microwave oven for light cooking. No laundry onsite. No parties or events allowed.

Guest favorite

Cabin in Rocky Point

4.9 out of 5 average rating, 507 reviews

Great little place just for a couple

The outdoor courtyard is especially nice and private ,with a fire pit, grill and comfortable chairs. It is a rustic location easy walking distance to North Shore Beach. If you want an ocean beach you can drive straight south for 20 minutes and reach Smiths Point State Park right on the ocean. The North Fork with its vineyards is a short drive and the Hamptons also only 30 minutes to West Hampton. You can fish, golf, walk among the wooded area and relax in peace. A pleasure. linen 100% cotton.

Superhost

Apartment in Ridge

4.74 out of 5 average rating, 165 reviews

The Silver Pine Cone

Welcome to the hamlet of Ridge. The gateway to Long Islands many treasures. Whether you are venturing out to the North Fork wineries or a scenic drive on the south shore beaches on your way to the Hamptons. A beautiful cozy private (not a shared space) full one bedroom downstairs lower level apartment, living room w/full size sofa sleeper, kitchen/dining room, full bathroom and a completely separate yard with patio furniture exclusively for your use. Everything you need to enjoy your stay.

Superhost

Guest suite in Miller Place

4.91 out of 5 average rating, 107 reviews

The Dogwood Inn - An eclectic north shore retreat

Off street parking, private porch, and private entrance. One bedroom with queen size mattress, sofa pull out (Q), & memory foam cot (T). Air mattress available upon request. Full eat in kitchen (spices/cookware/dishes etc. provided), full bath w/ stall shower. Free WIFI. Children Welcome. Located approx 1 mile from Cedar Beach. 8 min drive to downtown Port Jefferson Village (ferry to/from CT here). Close to restaurants, shopping, farms, park & playgrounds, vineyards, & SB University.

Guest favorite

Place to stay in Coram

4.99 out of 5 average rating, 108 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 favorite

Apartment in Port Jefferson Station

4.9 out of 5 average rating, 125 reviews

The Elite Enclave

Welcome to our newly expanded and renovated Airbnb home! This elegant and modern space has been meticulously designed to provide travelers with a comfortable and unforgettable experience. Outfitted with state-of-the-art amenities and conveniences, every detail of this home has been carefully considered with your comfort in mind. Ideally located just an 8-minute drive from the Bridgeport & Port Jefferson Ferry. We are dedicated to making your stay with us truly exceptional.

Guest favorite

Apartment in Shirley

4.95 out of 5 average rating, 113 reviews

Boho Beach Vibez Retreat! Private entrance

"Experience a different kind of stay with our unique Airbnb, the 'Boho Beach Vibez” This cozy 1-bedroom apartment , that’s approximately 500sqft is situated on the first level of our home with a separate entrance . Located in a prime area of our town, you'll find yourself just minutes away from all the stores, restaurants, highways, and within walking distance of hiking trails, the Carman’s river, and 5 miles from Smith Point beach. NOTE : hosts live on top level .

Top guest favorite

Apartment in Shirley

4.98 out of 5 average rating, 53 reviews

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.

Guest favorite

Guest suite in Stony Brook

4.8 out of 5 average rating, 646 reviews

Studio in Stony Brook

We have contactless check-in procedure & fully private entrance. Please contact with any questions! Large clean studio space that is totally private from the main residence. Private bathroom with toiletries included. Close to beaches, shopping, and SUNY hospital and campus by car or bus. Pull-out loveseat with twin size mattress available for an extra charge. (Book for “3 Guests” for this regardless of occupancy so we know to prepare the bed.)