House holiday rentals in Fire Island Pines

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Top-rated house rentals in Fire Island Pines

Guests agree: These houses are highly rated for location, cleanliness and more.

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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

4.94 out of 5 average rating, 191 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

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

4.97 out of 5 average rating, 230 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

Guest favourite

An outdoor deck space is surrounded by lush bamboo. Several wooden chairs and a picnic table are arranged for seating, offering a serene environment for relaxation. The area is shaded by leafy trees, contributing to a calm atmosphere.

Home in Fire Island

4.83 out of 5 average rating, 121 reviews

Fire Island Getaway! Weeks/Weekends/Midweeks!

VILLA ÉTOILE: 100 Yards/meters from Fire Island's best beach in a quieter, family area. Our simple 3-bedroom classic bungalow sleeps up to 6. Two bathrooms (1 w/shower). Whole-house A/C in summer! Screened windows & fans; front & back decks + balcony. Huge outdoor shower, BBQ, bikes, wagon, port-a-crib, games, 2 TVs, Netflix, beach chairs/umbrellas/toys, full cooking gear, condiments, etc. We rent to families & QUIET groups who agree to STRICT noise rules. Parties NOT allowed! Minimum age 25.

Guest favourite

A calm waterfront scene features a vibrant sailboat gliding across the bay, surrounded by green marshland. A wooden dock leads into the water, with several colorful chairs positioned for relaxation. Soft hills and houses line the distant shore under a gentle mist.

Home in Mastic Beach

4.94 out of 5 average rating, 133 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

Breathtaking Waterfront home with 37 foot heated indoor pool. 3 Bedrooms plus a 800 Sq/Ft master bedroom with wood burning fireplace. WiFi, 3rd floor entertainment room with 120 inch screen movie projector, karaoke, fooseball, pool table. Wraparound terrace, sunroom, 45ft dock with launching ramp, putting green, sand trap, outdoor kitchen, bar & stone patio with tables & BBQ grills & fire pit. Ability to catch abundant fish & blue crabs right from the dock. Picture tells a thousand words.

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, 169 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.

Guest favourite

Home in Mastic

4.96 out of 5 average rating, 173 reviews

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

Guest favourite

A patio is shown with a wooden table and a dark wicker chair overlooking a scenic view. A clear sky with scattered clouds is visible in the background, along with open fields and distant structures. Utility poles line the road, adding context to the setting.

Home in Patchogue

4.93 out of 5 average rating, 150 reviews

Joyful Beach House, viewing The Great South Bay

Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

Superhost

A light-filled living area features a comfortable sofa adorned with nautical-themed pillows. A wooden coffee table rests on a woven rug, while a stylish floor lamp and wooden chair enhance the space. The ceiling showcases exposed beams, adding character to the room.

Home in Cold Spring Harbor

4.86 out of 5 average rating, 309 reviews

Nautical Farm House on Working Farm with Animals

Completely renovated 3 bedroom home on working farm with fire place and piano. Lux kitchen features stainless steel appliances, Sub-zero refrigerator, and marble counters Private, fenced backyard with BBQ. Farm has goats, pigs, chickens, bee hives, ducks, and on-site cafe and bakery. Close to Huntington village, bike trails nature walks, restaurants, parks, and the beach. Fast wi-fi, laundry access and pet friendly. New beds and baby grand piano. Bedrooms have black out curtains.

Superhost

The open living area features a custom slate pool table with a vibrant arrangement of billiard balls. A modern kitchen is visible in the background, including sleek cabinetry and a refrigerator. A tasteful seating area includes a fireplace and a large wall-mounted television.

Home in Shirley

4.94 out of 5 average rating, 266 reviews

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy

Welcome to Coast to Coast - the perfect getaway from NYC! You may have heard about our new little secret - but you’ll have to come see it for yourself to believe it! Step back into prohibition era Long Island in our hidden speakeasy! Right by Smith Point Beach, we provide accommodations that go above and beyond- this is not your average AirBnB! Soak up the sun at one of LI's top beaches, then enjoy complimentary Netflix, Hulu, cable and more while you shoot pool or play games.

Guest favourite

A black swan-shaped float rests in a clear, inviting pool. Surrounding the pool are wooden deck areas furnished with lounge chairs and a dining table, accommodating six. The serene setting includes shaded areas provided by umbrellas, framed by lush greenery in the background.

Home in Fire Island

4.89 out of 5 average rating, 18 reviews

FI Pines Updated 3 BR/2 BA with Heated Pool, Spa

Interested in a longer stay, customized dates, or have any questions? Don’t miss your chance to stay. Message us TODAY! Nestled high in the tree tops, this bright and airy 3-bed/2-bath updated bungalow is your dream retreat. Enjoy seamless indoor/outdoor living with deck access from every room, an expansive heated pool deck with outdoor shower and spa, & a serene rooftop garden. 8-minute walk to/from the ferry—your FIP escape awaits! Where FIP Charm Meets Authentic Hospitality.

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, 106 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

A living room is highlighted by a cozy sofa draped with a light throw. A glass coffee table sits atop a soft rug. A fireplace is set within a white mantel, complemented by plants and framed art that add a touch of character.

Home in Bellport

4.9 out of 5 average rating, 135 reviews

The Stella ~ A 1920s Beach Bungalow

Welcome to The Stella, a thoughtful 1920's home set in the heart of Bellport Village. This is the place for a summer romance, a family gathering, or a creative re-centering. Inspired by the subtle palette and refined geometry of the American artist Frank Stella—who often spent time on Long Island—The Stella enjoys close proximity to many beaches and wetlands.