Holiday rentals in Fire Island

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Top-rated holiday rentals in Fire Island

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

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Guest favourite
A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.
Home in Rye
4.91 out of 5 average rating, 129 reviews

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

Guest favourite
A vibrant blue exterior of the cottage is complemented by wooden decking, leading to an inviting entry. A couple of white chairs provide a space to relax, while colorful buoys hang decoratively. Glass bottles scatter along the ground, adding character to the outdoor area.
Home in Fire Island Pines
4.94 out of 5 average rating, 190 reviews

Fire Island Pines Mid-Century Beach Cottage

This Fire Island Pines house is an Early-Pines artist's paradise. Our house was once written up in House & Garden (photo spread at house), and provides an authentic bohemian Pines lifestyle: Layered decks descend the hill for sun and shade with main decks surrounding, plus a roof-top deck for 4, all make for a party-friendly space; secluded on two old-growth lots for plenty of get-away privacy. Beautiful white-sand beach only 150 steps away. You'll fall in love with this unique Pines experience.

Guest favourite
A bright living room area features a sectional sofa and a coffee table set on light carpet. A smart TV is positioned on a low stand, and natural light enters through a skylight. Decorative curtains frame the window, adding a touch of style.
Serviced apartment in Medford
4.88 out of 5 average rating, 160 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!

Top guest favourite
An expansive deck offers a view of the Great South Bay, with a mix of comfortable seating options, including lounge chairs and a sectional sofa. The area is complemented by manicured green grass and a wooden railing, providing a serene backdrop for outdoor relaxation.
Home in Shirley
4.98 out of 5 average rating, 225 reviews

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

Top guest favourite
A two-story gray house with a welcoming entryway is set against a backdrop of trees. The exterior features multiple windows, a front porch, and a side door. A well-maintained lawn and paved pathway lead to the entrance, creating an inviting atmosphere.
Flat in Sayville
4.97 out of 5 average rating, 189 reviews

1 bedroom apt In the beautiful town of Sayville

Second floor apartment ideal for a couple in the heart of Sayville, South Shore Long Island. 5 minute walk from LI Railroad, 2 minute walk to quaint town and a 20 minute walk to Fire Island Ferry terminal for a beautiful ride to the renowned Fire Island beaches. No need for a car, just hop on the train to Sayville station and everything is in walking distance. Ferries go to Cherry Grove Fire Island Pines and Sailors Haven where you'll enjoy the best beaches and nightlife on the east coast.

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
4.96 out of 5 average rating, 109 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.

Guest favourite
A neatly made bed is positioned in a softly lit room, featuring a light blue bedspread and decorative pillows. Two bedside lamps provide warm lighting on either side, creating a calm and restful environment.
Flat in Bayport
4.92 out of 5 average rating, 144 reviews

Private Studio in Lovely South Bayport

Studio offers a private, sequestered nook in quiet Bayport. The 350 sq ft. offers: Queen bed (Drexel Heritage pillow-top mattress) with natural fiber bedding, 2 king pillows. Large bathroom with roomy shower, good towels. We use natural laundry soap, essential oils. Wifi, Roku television as well as contactless check-in & out with keyless locks. Close to ferries to several FI beaches. Close to main street for services/ restaurants. Walk to two parks. Dedicated off-street parking. NO SMOKING

Guest favourite
A well-lit bedroom features a spacious bed with decorative bedding, positioned against a soft blue wall. Natural light enters through large windows, adorned with sheer curtains. A compact dresser stands nearby, and an elegant table lamp adds functionality to the cozy space.
Home in Holbrook
4.91 out of 5 average rating, 297 reviews

Cozy studio

We are 10 minutes away to MacArthur Airport in Islip, 5 minutes to shopping center where you can find supermarkets, restaurants, and stores. We are 10 minutes away from LIRR train station where you can get a ride to Manhattan. Although the studio is centrally located a car or Uber is recommended,. You'll have your own bathroom, kitchen with microwave, coffee maker, toaster, fridge, air conditioner, tv with cable and internet. Our study is a FREE SMOKING PLACE! Not smoking or vaping!

Top guest favourite
A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.
Cottage in Weston
4.97 out of 5 average rating, 186 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

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
4.98 out of 5 average rating, 191 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+

Top guest favourite
A cozy living area features a plush gray couch adorned with decorative pillows. Vibrant blue walls complement the stylish kitchen cabinetry in the background. A large flat-screen television displays a scenic beach image, while a sleek desk sits nearby. Soft lighting adds to the inviting ambiance.
Flat in Shirley
4.95 out of 5 average rating, 135 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 favourite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guest house in Pound Ridge
4.94 out of 5 average rating, 103 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Popular amenities for Fire Island holiday rentals

When is the best time to visit Fire Island?

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Avg. price$336 SGD$352 SGD$325 SGD$357 SGD$431 SGD$543 SGD$690 SGD$682 SGD$517 SGD$370 SGD$354 SGD$361 SGD
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Frequently Asked Questions

  • How is the weather in Fire Island?

    Fire Island experiences a temperate maritime climate. Summers are typically warm, with temperatures around 80°F (27°C), while winters can be chilly, averaging 32°F (0°C). It's worth noting that the island can be foggy in spring and fall, adding a sense of mystery to your exploration.

  • What are some of the best things to do in Fire Island?

    You can explore the Sunken Forest, a rare maritime holly forest, or visit the Fire Island Lighthouse, a historically significant structure with stunning views. You might also enjoy walking around the car-free communities, swimming in the ocean, or watching wildlife at the Fire Island National Seashore.

  • What is the best time of year to visit Fire Island?

    The most frequented time to explore Fire Island is summer, between June and August. During this period, you can enjoy the Fire Island Dance Festival and the annual Fourth of July Parade. Fall is also enjoyable as it brings the annual migration of the monarch butterflies.

  • What are the best places to stay in Fire Island?

    There are quite a few communities on Fire Island that make for fantastic bases from which to explore. Some often recommended ones are Ocean Beach, Cherry Grove, Fire Island Pines, and Saltaire. Each community has its unique charm and character.

  • What are the best places to visit in Fire Island?

    Fire Island boasts many interesting sites to explore such as the Fire Island Lighthouse, the Sunken Forest, and the Fire Island National Seashore. The communities of Ocean Beach, Cherry Grove, Fire Island Pines, and Saltaire also offer unique local experiences.

  • What are some hiking trails in Fire Island?

    Fire Island has numerous hiking trails that let you experience its natural beauty. Some of the frequently suggested trails include the Sunken Forest Trail, the Bayside Loop trail at the Fire Island Lighthouse, and the trail at the Otis G. Pike Wilderness Area.

  • What are some family activities to do in Fire Island?

    Family-friendly activities on Fire Island include beach time, visiting the Fire Island Lighthouse, exploring the Sunken Forest, and bird watching at the Fire Island National Seashore. You can also take a leisurely stroll through the car-free communities, or engage in water sports like paddleboarding and swimming.

  • What are some of the best day trip ideas in Fire Island?

    Day trips can take you to the beautiful Robert Moses State Park, the Fire Island Lighthouse or the Sunken Forest. You can also spend a day exploring the communities of Ocean Beach or Cherry Grove, swimming in the ocean, or bird watching at the Fire Island National Seashore.

  • Are there vacation rentals with a dedicated workspace in Fire Island?

    Yes! Work meets play with ease at over 430 vacation rentals in Fire Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in apartment rentals in Fire Island?

    Experience the best of Fire Island with our apartment rentals, starting at about $10 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 Fire Island?

    Four-legged friends are welcome in Fire Island. Choose from more than 390 vacation rentals for guests traveling with pets.

  • Do apartment rentals in Fire Island have free parking?

    Absolutely! We offer over 60 apartment rentals with free parking in Fire Island. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Fire Island have self check-in?

    Absolutely! We offer over 10 apartment rentals with self check-in in Fire Island. Enjoy a tailored experience with all the comforts you desire.

  • Are there Fire Island guesthouse rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 guesthouse rentals with pools in Fire Island, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Fire Island have a bbq area?

    Absolutely! We offer over 30 apartment rentals with a bbq area in Fire Island. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Fire Island have a gym?

    Absolutely! We offer over 110 house rentals with a gym in Fire Island. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Fire Island?

    Fire Island has more than 540 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Apartment Rentals in Fire Island?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with self check-in, over 10 homes with a gym, over 30 homes with a bbq area, over 60 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Fire Island

  • Total holiday rentals

    Explore 1,050 holiday rentals in Fire Island

  • Nightly prices starting at

    Fire Island holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 26,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    650 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 390 rentals that welcome pets

  • Holiday rentals with a pool

    350 properties feature pools

  • Rentals with dedicated workspaces

    430 properties have a dedicated workspace

  • Wifi availability

    1,010 of Fire Island holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Pet-friendly, Laptop-friendly workspace and Gym across Fire Island rentals

  • 4.9 Average rating

    Fire Island stays are highly rated by guests – averaging 4.9 out of 5!

  • Nearby attractions

    Fire Island’s top spots include Fire Island National Seashore, Islip Cinemas and Plaza Cinema & Media Arts Center

Destinations to explore

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