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.

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.

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.

Pines Paradise

This is a newly updated, fully air conditioned 4-bedroom/4-bathroom house with a classic mid-century Fire Island Pines vibe. Large wrap-around decks on two levels provide ample outdoor space for sun, fun and dips in the pool. Located on one of the direct walks to the beach, you can get your toes in the sand in under a minute from the front door. **All weekly reservations begin on Thursdays. Rentals may be extended in weekly increments depending upon availability.**

Fire Island Pines getaway

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 2nd level unit with private outdoor space of this 2 unit home.

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.

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.

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.

"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.

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