Holiday houses in Fire Island Pines

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.

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

2 BR Private Suite w/Private Living Room & Kitchen

Two bedroom, one bathroom private poolside suite in Fire Island Pines with a large private living room and kitchen. Private entrance with a view of the pool. Three minute walk from the harbor and three minute walk to the beach. One bedroom has a queen bed, the other a bunk bed. The bathroom has a walk-in shower and Toto washlet. Shared hot tub, 91 degree heated pool, and outdoor shower. Shared roof deck with a 360 degrees view of the Pines. Small gym beneath the house. New construction (2018).

FI Pines - 3 bedroom / 2 bath beach house

Renovated interior designed to elevate your FI Pines experience. Each bedroom strikes a balance between comfort and functionality with sliding glass doors to the deck and a workstation for travelers who need to plug-in. The kitchen includes quartz countertops and a dining table for 6—ideal for enjoying meals prepared with a full assortment of kitchenware. Living space accommodates your entire group with a large L-couch, recliners, Smart TV, and JBL speakers for movie nights at home.

Bayfront Retreat • 3-bedroom ensuite + hot tub

What Makes This Home Special • True bayfront living with sweeping views • Three ensuite bedrooms for privacy • Large sliding doors for indoor/outdoor flow • Bayfront deck with hot tub and loungers • Steps to town, dining, nightlife, and the ocean • Clean, intentional mid‑century coastal design Extras We offer a curated selection of waterfront and beach gear, including Kayaks, Paddle Boards, Boogie Boards, Fishing Poles, Crabbing Gear, Beach Chairs, Umbrellas, and Beach Towels.

Studio Apt in Cherry Grove, FI.

Studio Apartment only a few steps from the beach at Dune Point Guesthouse. Located in Cherry Grove, Fire Island. Only accessible by Ferry! Adults Only Resort! Newly renovated space with full kitchen, bathroom, one queen size bed and two twins. Great space for couples, with the option of having a friend over, cook, BBQ, enjoy the beach. Located in Fire Island's town of Cherry Grove, laid back, crazy fun place with restaurant, clubs and bars.

The Sandbox

Step back in time and enjoy modern comforts in this iconic beach house. 3 bedrooms and 2 bathrooms comfortably sleep 6 guests. The home was originally designed in 1960, inspired by one of Horace Gifford’s earliest floor plans. The house has been recently updated in 2024 with contemporary finishes while preserving the stunning mid-century modern aesthetic. All furniture and beds are brand new for your comfort.

Guest House retreat with amazing pool !!!

Slice of Heaven #2 Bellport Village, a destination town overlooking the great south bay as seen in Coatal Living's top places to vacation. Written by Coastal Living: a gorgeously unassuming little seaport on long Island's South Shore, this village holds a royal flush of pleasures- A small town community feel, colonial style architecture, and even its own performing arts center, all 90mins from NYC.

"SOUTH APT." Renovated 1 Br Apt. In Great Location

The 1 Bedroom "South Apartment" is located in our newly renovated beach house, perfectly located just seconds away from the ocean and only three blocks from the harbor in Fire Island Pines. The house has 2 outdoor decks with a pool and a hot tub, both with ocean views. The apartment has a queen size bed, Heat & A/C units in every room, internet, TV and much more!

Fire Island Pines Waterfront Oasis - Pool & HotTub

🌈❤️‍🔥🏖🌲⛴☀️ FIP WATERFRONT EAST END OASIS 🧜🏼‍♂️👬🪩💃👑⛱ 🏡2 Bed, 2.5 Bath 💦Pool 🛁HotTub 🧘‍♂️Outdoor gay-zebo 🚿Best showers in Pines 🌅 Bay views from beds 🌊 Ocean views from rooftop 📺 72” TV 👨‍💻FIOS high speed internet 👑 Fabulous drag closet 💅🏼 ⛱ Beach chairs, towels, umbrellas provided 🤳🏼Video tour available 😘

Charming Quintessential Beach House

This is a charming and quiet house very close to the harbor in Fire Island Pines. We maintained and everything you need with a heated pool, central air, good towels and sheets. This is the best part of the Pines with only a 5 minute walk to town and the beach. The house is manageable for a couple to two couples.

Classic Yacht in the Fire Island Pines

We would love to share our beautiful yacht with you at the Pines. Both sunrise and sunset views are breathtaking from the yacht. We are close to town yet in a private location. It is the perfect spot for the Pines Party weekend! We do three hour sunset cruises as well for an additional fee. 🌅 Max 6 guests