Holiday rentals in Fire Island Pines

A vibrant blue exterior of the cottage is complemented by wooden decking, leading to an inviting entry. A couple of white chairs provide a space to relax, while colorful buoys hang decoratively. Glass bottles scatter along the ground, adding character to the outdoor area.

4.94 out of 5 average rating, 204 reviews

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.

Superhost

5.0 out of 5 average rating, 4 reviews

Private Cherry Grove Home with Saltwater Pool

* limited dates for 2026 season* Enjoy a stylish experience at this centrally-located place just one block from the ferry, market, restaurants, and nightlife, and only steps from the beach. Thoughtfully redesigned, the home features an open-concept floor plan with soaring cathedral ceilings, beautifully preserved original woodwork, and sophisticated high-end finishes throughout. Step outside to your own private retreat, complete with a brand-new saltwater pool and expansive wraparound sun decks.

A large deep swimming pool is framed by wooden decking, offering ample space for relaxation. Sun loungers are arranged alongside the pool, surrounded by vibrant greenery. A shaded dining area is visible in the background, enhancing the outdoor space.

4.6 out of 5 average rating, 83 reviews

7 bdrms all w/AC, pool, hot tub, bay view $0 Fees

Escape to our beach house in the Pines community. No extra Airbnb fees - just a modest cleaning fee. The beach house has a large deep swimming pool, 6 person hot tub and multiple decks (including the famous sunset deck) to go along with the 7 bedrooms, 5 bathrooms and 2 separate common areas, each with their own kitchens and outdoor grills. The house faces the bay and is located along a quiet path with little foot traffic; yet both the beach and the harbor are only a 10 min walk from the house.

An outdoor deck features a dining table with chairs surrounded by greenery. Sun loungers are positioned for relaxation under a bright sky. A hanging flower basket adds a touch of color, complementing the natural setting created by the surrounding trees.

5.0 out of 5 average rating, 10 reviews

A Charming Fire Island Pines Beach House Getaway

A classic Fire Island Beach House, perfect for memorable getaways with friends. A large living space and open kitchen, 3 bedrooms with copious storage, large outdoors deck, 1.5 bathrooms and an outdoor shower. The house is nestled among large trees for privacy. The house is stocked with all basics. 2 mins to the ocean, and 7 min walk to town and stores. We have availability throughout the summer, though book early. Min 4 night stay, discounts on full weeks, open to special deals. DM to discuss!

A light-filled living area features a large L-shaped couch with colorful cushions, complemented by two patterned armchairs. A Smart TV is mounted on the wall, and sliding glass doors open to a spacious outdoor area with patio furniture. Exposed wooden beams highlight the ceiling.

5.0 out of 5 average rating, 13 reviews

FI Pines - 3 bedroom / 2 bath beach house

Our single story beach cottage is designed to elevate your FI Pines experience. Bedrooms mix comfort and functionality with sliding glass doors to the deck and workstations for guests 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. *rates now include mandatory 15.5% AirBnb fee

A spacious living area features comfortable seating arrangements, including soft sofas and a central coffee table. Large windows invite natural light, while a sleek television is mounted above a modern fireplace. The open layout connects to a dining area, enhancing the communal atmosphere.

5.0 out of 5 average rating, 11 reviews

Pristine 7Br house 500’ to beach

A great place for an amazing time! …. Your friends will be blown away by your "FIND" New renovation w/new, gorgeous furnishings, 500f t from the Ocean and it will be where your crew has the best week of their year. 7 BRs are beautifully decorated - 2 King En-suites each with a private coffee bar. One Queen En-suite and 2 Queens with a shared jack&jill En-suite and finally 2 more queens. Four & a half baths, a heated pool and 3 level deck incl a rooftop deck This is your Pines place !

A black swan-shaped float rests in a clear, inviting pool. Surrounding the pool are wooden deck areas furnished with lounge chairs and a dining table, accommodating six. The serene setting includes shaded areas provided by umbrellas, framed by lush greenery in the background.

4.89 out of 5 average rating, 27 reviews

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.

4.97 out of 5 average rating, 107 reviews

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.

4.85 out of 5 average rating, 92 reviews

The Legendary Pyramid House

Architectural masterpiece (b. 1961) w/ spectacular views and privacy. A soaring ceiling and a wall of glass overlooking the dunes, the ocean and the bay. Beneath, the enormous master suite looks out to the dunes on one side and the pool deck on the other. Across the salt water pool are 2 guest cabana bedrooms and a bathroom. Cooling ocean breezes complement central AC in this sophisticated, relaxed compound. Heated salt water pool and central AC installed June 2026.

4.91 out of 5 average rating, 11 reviews

Fire Island Pines paradise.

Enjoy a stylish experience at this centrally located property. This classic, ideally located home has just been refreshed for the season. New Jacuzzi brand hot tub, outdoor shower, new premium beds, 55” 4K smart TV, FIOS high speed internet, stocked kitchen. Prime location! 2 minute walk to the beach and 5 minute walk to the Pines ferry dock, bars, restaurants, liquor store and local market. Entire first level of this two unit home with private outdoor space.

A serene outdoor space features a heated pool surrounded by lush greenery. Lounge chairs arranged on a wooden deck invite relaxation. Colorful pool floats rest on the water's surface, and a simple stone table is positioned nearby, enhancing the tranquil atmosphere of the garden.

4.92 out of 5 average rating, 73 reviews

Fire Island Pines Historic Art Home w/Heated Pool

Historic architect-designed home located directly on Fire Island, in a quiet residential setting just steps from the ocean and less than a 10-minute walk to the Fire Island Pines Harbor. Designed by renowned architect Horace Gifford, this Fire Island Pines home offers four air-conditioned bedrooms, curated art-filled interiors, a heated pool, outdoor hot tub, and expansive terrace—an exceptional Fire Island rental combining design, comfort, and location.