Holiday rentals in Fire Island Pines

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Top-rated holiday rentals in Fire Island Pines

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Guest favourite

Home in Copiague

4.9 out of 5 average rating, 21 reviews

Harbor Water Views

Situated just one house away from the picturesque Great South Bay on a quiet cul-de-sac, this rare gem in an American Venice setting boasts southern exposure and underwent updates in 2019. This charming residence is a 2-bedroom, 1-bathroom Classic Cape featuring a generously sized deck that was revamped in 2021. Conveniently located minutes away from shopping, beaches, and parks, this home provides a secluded retreat from the hustle and bustle, offering tranquility away from traffic and noise.

Guest favourite

Home in Fair Harbor, Fire Island

4.93 out of 5 average rating, 27 reviews

Chill Beachfront Cottage Amazing Bay/Sunset Views!

Charming, Classic Beach Cottage right on the BEACH! with Panoramic Views & Sunsets on the Great South Bay! Summer on Fire Island is truly paradise. The ocean is sensational, the weather is perfect, the sunrises & sunsets are spectacular, the residents are friendly & creative, & life is WONDERFUL. Our Cottage has 5 Bedrooms with 8 beds that sleep 11. Like Fair Harbor, it has a casual, laid back vibe that is comfortable & enjoyable for people of all ages. * KAYAKS are AVAILABLE! Ask Roberto

Superhost

Cabin in Shirley

4.87 out of 5 average rating, 153 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

Flat in Ocean Beach

4.8 out of 5 average rating, 5 reviews

2BR Apartment with Terrace

This modernized two bedroom apartment with terrace views of the bay offers a perfect blend of comfort, convenience, and coastal allure. Equipped with a fully stocked kitchen, Smart TV, WiFi and washer/dryer. Three Beach chairs and umbrella. Sleeps 5 comfortably with 3 twin beds and 1 full bed. Located steps away from an array of restaurants, bars, and shops, with the beach just a 5-minute stroll away. Don't miss out on this perfect coastal retreat – book now for an unforgettable vacation!

Top guest favourite

Home in Ocean Beach

5 out of 5 average rating, 43 reviews

Sunny Spacious Pet Friendly Steps from the Beach

This ideally located four-bedroom home is the perfect spot for your family's vacation. The home features a spacious deck, central air conditioning, WiFi, 4 Smart TV's, a Sonos sound system and YouTube TV. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. There are 2 full bathrooms as well as an outdoor shower. Fully equipped including beach chairs, towels, 5 bikes, 2 wagons and beach toys for the kids. Sleeps 10.

Superhost

Guest suite in Massapequa

5 out of 5 average rating, 4 reviews

Cozy Couples Winter Retreat!

Nestled on a serene canal of the South Shore of Long Island, our charming first floor apartment offers the perfect blend of comfort and tranquility. Ideal for couples, solo travelers or small families, this cozy retreat provides a unique experience. Located just minutes away from the LIRR and a 45 minute train ride to NYC Penn Station, you will fid this aparmtnet to be the pefect fit for a winter getaway. Indulge in our Hot Tub that is covered under a mezzanine and open all year round.

Guest favourite

Guest house in Copiague

4.91 out of 5 average rating, 56 reviews

Palms by the bay: Waterside Cute Cozy Cottage

Kick back in this cozy cottage on the Great South Bay of Long Island. Sleeps up to 6 guests. Enjoy bay views from your private yard that include a propane grill, fire pit, & anti-gravity chairs. Perfect for fishing or kayaking from your own dock. Just an hour train ride from Manhattan and a 30-minute drive to Robert Moses Beach (where you can walk to Lighthouse and enjoy the beach). Ideal for a relaxing or adventurous getaway. Book now and experience the serene beauty of the bay!

Guest favourite

Home in Mastic

4.88 out of 5 average rating, 102 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Guest favourite

Home in Coram

4.89 out of 5 average rating, 94 reviews

Entire independent Apt close to Airport and Ferry

Enjoy the simplicity of this quiet and central accommodation, where you can have close to you the busiest places in Coram New York. You can enjoy a good wine at Harmony Vineyards. You can enjoy the Splish Splash Water Park with your family And if you like everything that has to do with the Marina an ideal place to visit is Danfords Marina. Come and stay with Julio and Karina, we will make your stay a good experience.

Guest favourite

Home in Mastic

4.95 out of 5 average rating, 140 reviews

Paradise Citadel hottub, Htd pool golf basketball

Welcome to summer 2025 at Paradise Citadel. Get ready to soak up the sun, swim in the sparkling pool, and explore all the amenities this property has to offer this summer. We're excited to host you in our property Feature, hottub, pool, putting green, Basketball court, firepits, volleyball net, pickball net. My wife and I can't wait for guests to explore this home and make memorable moments with their loved ones

Superhost

Cottage in Ocean Beach

4.85 out of 5 average rating, 81 reviews

☀️NEW LISTING! 2BR Oceanview Hideaway☀️

New Listing in the Exclusive Corneille Estates located in Ocean Beach, Fire Island Soak in the sun and ocean views in this Fire Island 2 bedroom peaceful retreat! Great for families, groups of friends or couples with kids. ★ Hurry and reserve your beach getaway before your dates are booked! ★ Linens and towels provided! ★Steps away from the beach, this beautiful beach cottage is spacious, clean and private!

Top guest favourite

Home in Bellport

5 out of 5 average rating, 24 reviews

Monkey Puzzle - Renovated Cottage in Bellport

Monkey Puzzle is affectionately named for a well known tree in the front lawn of this house, it seems that everyone in town is familiar with our Monkey Puzzle tree. We purchased this house last summer and have done a total renovation to get it ready for Summer 20024. Everything in Monkey Puzzle is brand new; including 2 bathrooms, kitchen cabinets and appliances, central air, and an amazing gunite pool.