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

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 Bedrooms with Ensuite Bathrooms + 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.

Pine Walk, Fire Island Pines-Close to everything!

Enjoy your stay at Pines in a private natural setting that will take you away from your worries, recharge your batteries, and offer you an unforgettable experience. This home features an open living/dining area with vaulted ceilings. Open gourmet kitchen with top of the line appliances. Heated salt water pool and sunny deck area with total privacy. Central Heat and Air conditioning. Two bed rooms, one King and one queen...perfect for a getaway for two couples!

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.

Fire Island Pines Treehouse

NEWLY RENOVATED Fire Island Pines home. Sits high in the trees in ideal location east of the harbor. 3 bedroom, 1 full, 2 en-suite half bath. Heat/AC and heated pool. All rooms open onto the pool deck. Or relax in the hammock or one of the many lounges. Prices vary during peak season and high demand, event and holiday weekends. Weekly is preferred but inquire with custom dates for adjusted pricing. Weeklies start on Thursdays.

Bellport Park | Pool, Fire Pit & Balcony

Wander Bellport Park is a secluded luxury retreat in the heart of Bellport. Enjoy evenings by the fire pit under the stars with forest views. Spend days by the outdoor pool, surrounded by the soothing sounds of nature. Al fresco dining shines with a dedicated area for intimate meals or lively gatherings. This exceptional getaway blends rustic charm with high-end comfort, offering an unforgettable experience for discerning travelers.

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!

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.