Family-friendly holiday rentals in Fire Island

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.

Indoor spaces · Kitchen · Bathroom

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.

Indoor spaces · Location · Amenities

Luxurious Waterfront Beach House On The Bay

Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay with private beach... The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the enjoyments the island has at your fingertips. Centrally located to all island destinations. 90 minutes from Manhattan - 15 minutes to West Hampton - 15 minutes to Fire Island Ferrys. Visit top winery’s WiFi

Family · Indoor spaces · Cleanliness

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)

Kitchen · Family · Layout

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Kitchen · Indoor spaces · Condition

New Listing-The Big Fish

Welcome to The Big Fish - Your home away from home! This charming beach cottage comfortably sleeps 8-10 with 4 bedrooms and 1.5 baths. In addition, there's a screened in front porch with sitting area. Outback has a large deck great for entertaining, relaxing plus an outdoor shower & BBQ. Handicap accessible with 1st floor bedroom. 8 beach chairs, 1 umbrella, 6 bikes & 1 wagon. Each bedroom has an air conditioner, and the main living area has an air conditioner. Space heaters only for heat.

Family · Indoor spaces · Quiet

The Stella ~ A 1920s Beach Bungalow

Welcome to The Stella, a thoughtful 1920's home set in the heart of Bellport Village. This is the place for a summer romance, a family gathering, or a creative re-centering. Inspired by the subtle palette and refined geometry of the American artist Frank Stella—who often spent time on Long Island—The Stella enjoys close proximity to many beaches and wetlands. Our original 1920's Cape Cod style home is full of old and new finds that appeal to curious journeyers and creative weekenders.

Family · Indoor spaces · Checkout

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

Family · Kitchen · Check-in

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!

Family · Kitchen · Biking

Waterfront Round House View

A unique little beach house on the south shore of long island with the most beautiful view. The house is located on a canal. Dock is available! **We have Paddle Boards, Surf Boards and 3- 2 person Kayaks onsite for you to use during your stay. You can get to the Great South Bay by paddling to the mouth of the canal. And you can get to Fire Island by hiring a Water Taxi to pick you up! The octagon house was built in the 1970s. It's recently been refreshed with all new beds & linens.

Kitchen · Indoor spaces · Laundry

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

Kitchen · Family · Parking

Bay Front Upper Level Cottage 47E

Beach front on the water. This paradise hosts its own private beach located on the bay. The house is close to the ferry and easily accessible to restaurants and everything Fire Island has to offer. The house boasts an outdoor shower, 2 bedrooms, kitchen, an indoor full bathroom, half bath, and a grill. Located on the 2nd floor and has views of the bay, beach, and sunset from every direction. Perfect for a family get away or a couple looking to have a romantic trip.

Family · Kitchen · Check-in