Holiday rentals in Islip

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Top-rated holiday rentals in Islip

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Top guest favourite
The cabin's entrance is framed by lush greenery and flowering plants. A wooden walkway leads to the door, and a small set of steps offers access. The rustic exterior features dark wood siding and a window for natural light.
Guest suite in Fire Island Pines
4.96 out of 5 average rating, 103 reviews

Fire Island Pines: Studio Cabin

Studio cabin (approx. 13.5 x 15 ft.) Functional, basic, rustic, atmospheric—It's just a little cabin in the woods. The shack can accommodate only 2 people max. Queen bed (sheets, blankets) Bathroom (shower/towels) Kitchenette (fridge, microwave, sink, dishwasher, dishes, cutlery, glasses) A/C (window unit) Fan Basic tv Internet Beach chairs/umbrellas, Outside shower The Pines is primarily a gay community, but welcoming to all. We love our wild deer and squirrels but no pets in the cabin

Guest favourite
Flat in Bay Shore
4.93 out of 5 average rating, 123 reviews

♡Cozy 1Br Apt,Garden Patio & Off Street Parking♡

Welcome to Bay Shore! Renovated, private 1 Bedroom Apartment with new windows, hardwood floors & a full kitchen. - Designated guest parking in driveway - First floor Apt., no stairs. Just step up from patio right into Apt. - Queen Size Bed - Living Room with Sofa bed for a 3rd guest - Smart TV - Fast 1024 Mpbs WIFI - Large Hallway Walk in Closet for luggage, etc. 2 Miles -Downtown Bayshore for Restaurants etc. 7 mins -SouthShore University Hospital 15 mins - Robert Moses State Park

Guest favourite
A comfortable living area features a light-colored sofa facing a wall-mounted television. A small dining table with two chairs is positioned nearby. Natural light enters through a door leading to an exterior space, and wooden flooring complements the overall layout.
Flat in Central Islip
4.95 out of 5 average rating, 133 reviews

Cozy studio w/ private entrance

Perfect for solo travelers or couples.This new, cozy studio is part of a larger home but fully self-contained w/ its own entrance. Inside, you’ll find: - A comfy living area with a pull-out twin bed and seating - A kitchen with essentials for light cooking - A private bathroom with shower, towels, and toiletries - High-speed Wi-Fi and a flat-screen TV Though attached to our home, your space is private. Located in a quiet neighborhood, close to attractions, restaurants, and transportation.

Top guest favourite
An outdoor deck is seen featuring a spacious octagonal hot tub. It overlooks a calm canal bordered by green grass and trees. Nearby boats are docked, and the tranquil water reflects the clear sky, creating a peaceful atmosphere.
Home in Oakdale
4.89 out of 5 average rating, 165 reviews

Waterfront Round House View

A unique little beach house on the south shore of long island with the most beautiful view. The house is located on a canal. Dock is available! **We have Paddle Boards, Surf Boards and 3- 2 person Kayaks onsite for you to use during your stay** You can get to the Great South Bay by paddling to the mouth of the canal. And you can get to Fire Island by hiring a Water Taxi to pick you up! The octagon house was built in the 1970s. It's recently been refreshed with all new beds & linens.

Top guest favourite
A side view of the guest suite reveals a private entrance with a white door and small steps leading up to it. A winding stone walkway is bordered by grass and gardens, providing access to the suite in a serene outdoor setting.
Guest suite in Bay Shore
4.96 out of 5 average rating, 289 reviews

Bay Shore's Private Guest Suite

Welcome to our cozy guest suite nestled within walking distance of the Fire Island ferries and conveniently close to local amenities! This private unit, attached to the main part of our home, offers a comfortable retreat for your stay. Step through your own private entrance into a welcoming living room, where you can unwind after a day of exploration. The bedroom features a queen-sized bed, providing a restful night's sleep, and an adjoining bathroom offers convenience and privacy.

Top guest favourite
Guest house in Islip Terrace
4.99 out of 5 average rating, 132 reviews

The Sunshine House

Enjoy your stay and visit the Bayard Cutting Arboretum, SUSA Orlin & Cohen Sports Complex, Robert Moses Beach; centrally located between The Hamptons Vineyard Wine Tours & Manhattan. This unique home was originally built in 1921 and has since undergone renovations with additions added to the original structure, including the three bedroom / bath guest wing with a private entrance from the main house. We provide beverages and continental breakfast. Please email us for more details!

Top guest favourite
The exterior of a charming cottage displays a white facade with dark blue trim and a welcoming front door. A well-manicured lawn featuring stepping stones leads up to the porch, surrounded by colorful flower beds and greenery.
Home in Patchogue
4.99 out of 5 average rating, 100 reviews

Hamptons Style Cottage close to everything!

Hamptons style cottage home is family friendly with a wonderful, fully equipped, kitchen to cook-in and spa inspired marble bathroom with huge shower and soaking tub to relax in. Rear patio with nicely landscaped yard shaded or unshaded by a large retractable awing. Located in Patchogue on a quiet block just a short walk to the fire island ocean ferries, restaurants, town's bustling main street, local bay beaches, and parks. Perfect for a weekend getaway or an extended stay!

Guest favourite
An outdoor seating area is set up with wicker chairs surrounding a gas fire pit, glowing warmly in the evening light. A well-maintained green lawn and white privacy fence create a serene backdrop, with soft string lights enhancing the inviting atmosphere.
Flat in Islip Terrace
4.96 out of 5 average rating, 205 reviews

Near all 1 BR - Full Kitchen, Backyard & Fire Pit!

Come stay at this beautifully renovated 1 bedroom apartment! Well-appointed for long-term stays or quick trips. ~ Propane Fire Pit ~ Private Sun-soaked backyard. ~ Full kitchen ~ Living room with sofa/futon for a 3rd guest ~ Queen bed ~ Full bathroom ~ Off-street parking for 1 car. This is a first-floor, ground-level apartment that gets lots of natural light. It is not a basement! :) Located in a quiet neighborhood and near all major highways. SmartTV. No cable TV. 21+

Guest favourite
A vibrant blue exterior is complemented by a bright yellow door, welcoming guests to the house. A stone pathway leads to the entrance, bordered by well-maintained greenery and flower beds, while trees provide a natural backdrop for privacy.
Cabin in Commack
4.84 out of 5 average rating, 251 reviews

Private Cabin in Multi Acre Park

I have a professional cleaning company come between all guests. The property is the only house on the street abutting several acres of wooded park land. Get the feeling of nature/privacy similar to being up state NY yet centrally located to Sunken Meadow Parkway, Northern State, LIE. Also near food stores and other essentials. 400 MBPS Internet connection for those who need a reliable internet connection for work! Living room has a pull out queen couch if a 3rd bed is needed.

Top guest favourite
A spacious living area displays rustic log walls and a mix of wooden and upholstered furniture. A comfortable leather sofa is positioned near a stone wood stove, while a colorful armchair adds charm. Natural light fills the room through windows adorned with patterned curtains.
Cottage in Patchogue
4.95 out of 5 average rating, 264 reviews

Quaint Cottage on Long Island's South Shore.

The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

Guest favourite
A spacious bedroom is presented with two beds side by side, surrounded by built-in bookshelves filled with books. Natural light filters through sheer curtains, illuminating the cozy nook with a window seat. A television is positioned in the corner, contributing to a welcoming atmosphere.
Flat in Bay Shore
4.93 out of 5 average rating, 121 reviews

Stay downtown & walk to Fire Island ferries

Spacious, private, ground floor space located in a mid-19th Century Mansard Victorian in Historic Bay District of downtown Bay Shore. Steps to dozens of restaurants, a spray park, beach, and ferry. 10 minute walk from LIRR. Child friendly. Please note that host’s family lives in the main house. Ask us about special add-ons to enhance your stay!

Top guest favourite
A comfortable living area is featured, showcasing a brown sofa with colorful pillows and a small table. Large windows are adorned with checkered curtains, allowing natural light to fill the room. A light fixture hangs above a blue cabinet, adding a touch of charm.
Guest house in Sayville
4.96 out of 5 average rating, 223 reviews

Great South Bay Cottage

Fantastic private cottage on Long Island's South Shore. Great access to the best beaches in the world (walk to bay, ferries to ocean). Short train ride to/from NYC, Wineries & The Hampton's. Experience the Island’s charm and culture. Enjoy Long Island summers. We employ a professional cleaning regiment.

Popular amenities for Islip holiday rentals

When is the best time to visit Islip?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Islip?

    Islip has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Islip?

    Experience the best of Islip with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Islip?

    Four-legged friends are welcome in Islip. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Islip?

    Yes! Work meets play with ease at over 10 vacation rentals in Islip featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Islip have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Islip. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Islip have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Islip. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Islip have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Islip. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Islip have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in Islip. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Islip

  • Total holiday rentals

    Explore 30 holiday rentals in Islip

  • Nightly prices starting at

    Islip holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 1,320 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Islip holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Islip rentals

  • 4.8 Average rating

    Islip stays are highly rated by guests – averaging 4.8 out of 5!

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