Fire Island Bear Weekend 2027

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• Modern oceanfront home featuring a 17-foot glass wall with panoramic Atlantic views and chic furnishings.
• Three bedrooms and two bathrooms upstairs, plus an additional queen room downstairs without a bathroom, accommodating up to eight guests.
• Expansive ocean deck with a pool and hot tub, located just four blocks from the town center.
• Equipped with central A/C, high-speed internet, flat-screen TVs, and a state-of-the-art A/V system for entertainment.

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• Spacious 4-bedroom, 4-bathroom beach house accommodating up to 8 guests, each bedroom featuring ensuite facilities and private outdoor access.
• Private heated pool deck with hot tub, outdoor shower, and alfresco dining area, complemented by a rooftop deck offering panoramic bay views.
• Open-concept kitchen with modern appliances, cozy living room with wood-burning stove, and entertainment options including Apple TV and Wi-Fi.
• Located just a few blocks from the harbor and commercial district, providing easy access to local attractions while maintaining a secluded ambiance.

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• A beautifully renovated four-bedroom home with convertible twin beds and a queen room, accommodating up to eight guests.
• Features a saltwater heated pool, hot tub, multiple decks with ocean views, and a gas BBQ for outdoor dining.
• Equipped with central A/C, high-speed Wi-Fi, and modern amenities for a relaxing stay.
• Located just a short walk from the beach, offering a serene oceanfront experience.

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• A spacious Rocky Mountain-style A-frame house featuring five bedrooms (three kings, two queens) and 3.5 bathrooms.
• Offers a gourmet kitchen, modern furnishings, and multiple private deck areas with a heated pool and hot tub.
• Equipped with central A/C, fireplace, and premium entertainment systems for a comfortable stay.
• Just a two-minute walk to the beach, making it ideal for group retreats.

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• A bright, open-concept home with high ceilings, skylights, and a multi-level deck offering rooftop views.
• Three bedrooms, each with private deck access, two full bathrooms, and an outdoor shower, accommodating six guests.
• Amenities include a pool, hot tub, central A/C, Sonos system, and wine fridge.
• Located steps from the beach, harbor, and bay, providing easy access to local attractions.

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• Check for availability for this property.
• A modern oceanfront retreat with a 17-foot glass wall offering panoramic Atlantic views, complemented by chic interiors and a Sub-Zero-equipped kitchen.
• Features three bedrooms, two bathrooms, and an additional queen room downstairs, accommodating up to eight guests.
• Enjoy a spacious ocean deck with a pool and hot tub, just a short walk from the town center.
• Equipped with central A/C, high-speed internet, and a state-of-the-art A/V system for entertainment.

More details and pricing.

• Check for availability for this property.
• A modern oceanfront retreat with a 17-foot glass wall offering panoramic Atlantic views, complemented by chic interiors and a Sub-Zero-equipped kitchen.
• Features three bedrooms, two bathrooms, and an additional queen room downstairs, accommodating up to eight guests.
• Enjoy a spacious ocean deck with a pool and hot tub, just a short walk from the town center.
• Equipped with central A/C, high-speed internet, and a state-of-the-art A/V system for entertainment.

More details and pricing.

Address: 1 Fire Island Boulevard, Fire Island Pines, NY 11782

• The biggest new add to the Pines venue map
• A daytime pool club tied to The Tryst Fire Island project, with daily
• pool service and Fri-Sun pool parties.
• Programming names rotating pool-party brands such as Cabana
• Boys, Daddy Issues and Well, Yes!
• Plus Middle Tea takeovers on Fridays and Saturdays.
• Open: Daily Mon–Thu 11am–6pm Fri–Sun 11am–10pm (seasonal)
• Website

Address: 36 Fire Island Blvd, Fire Island Pines, NY 11782, USA

• Legendary gay nightclub at the heart of Fire Island Pines.
• Indoor dance floor connects to spacious outdoor decks.
• House music and guest DJs drive the weekend energy.
• Busy summer parties attract a loyal returning crowd.
• Key stop on the island’s warm-weather party circuit.
• Open: Seasonal, typically Fri-Sun 7pm-4am
• Website

Address: 42 Harbor Walk, Fire Island Pines, NY 11782, USA

• Daily gay social event since 1966 in Fire Island Pines.
• Starts at 4 PM with music and dancing on the harborfront deck.
• Features signature cocktails and a lively atmosphere.
• Serves as a prelude to evening activities in the area.
• Remains a cherished tradition for LGBTQ+ visitors.
• Open: Daily 4 PM–6 PM (seasonal)
• Website

Address: 42 Harbor Walk, Fire Island Pines, NY 11782, USA

• Seasonal gay bar and restaurant in Fire Island Pines.
• Famous for Low Tea events and drag brunches.
• Waterfront setting with cocktails and relaxed dining.
• Draws a loyal summer crowd from across the Pines.
• Long-running social hub within the gay community.
• Open: Mon–Thu 6pm–9pm, Fri–Sun 11–12am
• Website

Address: 36 Fire Island Blvd, Fire Island Pines, NY 11782, USA

• Gay nightclub and bar located in Fire Island Pines.
• Features a spacious dance floor and outdoor deck.
• Hosts themed events, including drag shows and movie nights.
• Popular among the LGBTQ+ community and visitors.
• Known for its energetic DJs and vibrant atmosphere.
• Open: Mon–Sun 6pm–4am
• Website

Address: 158 Bayview Walk, Cherry Grove, NY 11782, USA

• LGBTQ+ bar and restaurant in Cherry Grove, Fire Island.
• Features drag shows, live DJs, and themed events.
• Offers waterfront dining with casual bar fare.
• Known for signature cocktails and festive atmosphere.
• Popular destination for locals and visitors alike.
• Open: Mon–Thu 12pm–4am, Fri 12pm–4am, Sat–Sun 9am–4am
• Instagram

Address: 1 Ocean Walk, Cherry Grove, NY 11782, USA

• Legendary gay nightclub in Cherry Grove with decades of history.
• Large indoor dance floor paired with a lively poolside area.
• Major drag productions and headline events across the season.
• Draws visitors from across Fire Island for big-night energy.
• A defining venue within the island’s gay party circuit.
• Open: Mon-Sun 8am-4am
• Instagram

Address: 178 Bayview Walk, Cherry Grove, NY 11782, USA

• Waterfront restaurant and bar in Cherry Grove, Fire Island.
• Offers American cuisine with seafood and sandwich options.
• Features outdoor seating and live entertainment events.
• Known for friendly staff and relaxed atmosphere.
• LGBTQ+ friendly venue currently open and operating.
• Open: Mon–Thu 12pm–8pm, Fri 12pm–9pm,
• Sat 11am–9pm, Sun 11am–8pm
• Instagram

Address: Harbor Walk, Fire Island Pines, NY 11782, USA

• Harbour-side café set in the busy core of Fire Island Pines.
• Serves breakfast, lunch, dinner, and late-night takeaway options.
• Outdoor seating keeps the space social and easygoing.
• Draws a largely gay crowd throughout the day and night.
• Smart stop for fast food between beach time and parties.
• Open: Mon-Sun 7am-12am
• Website

Address: 1 Dock Walk, Cherry Grove, NY 11782, USA

• LGBTQ+ friendly bistro in Cherry Grove, Fire Island.
• Offers American Nouveau cuisine with fresh seafood options.
• Features 180-degree views of the Great South Bay.
• Known for inventive cocktails and welcoming atmosphere.
• Popular dining spot among locals and visitors.
• Open: Fri–Sun 5pm–10pm
• Website