Vacation 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.

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.

Gorgeous Beach Home Steps From Ocean! Relax n live

Best location on Fire Island/Ocean Beach!!Literally Steps from Ocean! Relax with your family in this beautiful ocean home getaway! FEATURES: -Steps From Ocean -Open living and dining room concept for entertaining - Spacious Porch to have morning coffee and watch the deer! -Split 5 Units Ducts HVAC - nicely cool house -Spacious EPI Decking for outdoor bbqs and relaxation!! -WIFI Steps from Ocean and close to all shopping/restaurants! Can sleep up to 6 adults and 4 kids! (With Pull out couch)

PINES Cozy Beach Hideaway with modern touches

NEW listing, owner occupied, 4 bedroom / 2 bathroom modern, classic beach house centrally located - 5 minute walk to Pines harbor and 2 minute walk to the beach. Comfortably sleeps 8 people; King or Queen sized bed in each room. Open kitchen and dining room space ideal for cooking and hosting intimate dinner parties. Spacious and fully furnished patio area located behind the house for ultimate privacy. Fully redecorated and central AC added in the Fall of 2021. Not a typical share house!

Pet-Friendly, 5 min walk to beach & ferry

Make yourself at home in this centrally located 4-bedroom retreat, perfect for a laid-back family beach vacation. The bright, open layout comfortably sleeps 10. Enjoy a spacious deck, central air, Wi-Fi, 4 Smart TVs, YouTube TV & Sonos. The home has 2 full baths plus an outdoor shower. And when it’s time to hit the sand, we’ve made it easy with 10 beach chairs, towels, 2 umbrellas, 10 bikes, 2 wagons & kids’ beach toys provided. Dogs are welcome too, so the whole family can come along!

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.

Bayfront Retreat • 3 Ensuite BR + 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.

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.

Promise Land, Fire Island Pines

@___promiseland___ Enjoy your summer in a 1,500 SF private beach house that sits on a beautifully landscaped 9,000 SF lot. The spacious living area has soaring ceilings and is equipped with a wood burning fireplace. The single- story house has three oversized bedrooms and sleeps 6 guests comfortably. This house, with its large heated swimming pool, hot tub, BBQ grill, and outdoor dining, is the pinnacle of the perfect indoor-outdoor beach lifestyle.

One Bedroom Apt in Cherry Grove

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! Recently renovated space with full kitchen, bathroom and one bedroom with queen size bed. 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.