Holiday rentals 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.

Charming Beach Cottage in OCEAN BAY PARK

Charming cottage located in the town of Ocean Bay Park, just steps from the beach. Open floor plan living room with breakfast bar/kitchen. Bedroom on main floor, unique loft bedroom upstairs looking over living room. Bathroom with shower plus outdoor shower. Lovely deck with BBQ, outdoor seating. 5th house from the ocean—walk to the beach and if you need refreshments you'll be back at the cottage in 90 seconds tops. Bikes and beach chairs included. We're a family neighborhood--no parties please!

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.

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.

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!

2BR Bungalow: Fire Island Pines

** Discounts begin at 4-day bookings ** 5 minutes from town. 2 bedroom bungalow (One king / One full) Roof deck, outdoor shower, jacuzzi, Sonos, (FAST) Wifi. Beach chairs / umbrellas. Everything that you need for the beach! Max 4 guests. No parties or loud music late at night. Not a party house - your party must be respectful of the neighbors.

Studio with Deck steps to the beach

Studio Apartment with private deck only a few steps from the beach at Dune Point Guesthouse. Located in Cherry Grove, Fire Island. Only accessible by Ferry! Adults Only Resort! Fully equipped kitchen, outdoor loveseat, table and chairs on you private deck... perfect for a few days stay, BBQ, cook, enjoy the beach

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