Family-friendly vacation rentals in Fire Island

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, 203 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.

Indoor spacesFamilyTV

4.97 out of 5 average rating, 227 reviews

A balcony view captures a serene beachfront scene at sunset, with gentle waves lapping at the sandy shore. A detailed metal chair is positioned on the deck, providing a quiet spot to enjoy the tranquil waters and cloudy sky.

Home in Niantic

Beachfront Paradise

Beautiful beachfront home available weekly in season third week of June through Labor Day) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.

FamilyKitchenAir conditioning

4.97 out of 5 average rating, 101 reviews

A spacious deck is furnished with a wooden table surrounded by six white chairs, offering ample space for relaxation. Two large umbrellas provide shade, while a view of the calm water and distant horizon can be seen in the background.

Home in Shirley

Stunning sunset charming waterfront home 4 seasons

Want to relax and enjoy the water and sunsets? This home has a very relaxed vibe, whether you are grilling outside, kayaking, going to the beach, reading a book as the sound of the waves gently wash up on shore or even enjoying a glass of your preferred beverage on the deck as you gaze into the horizon, there is a sense of comfort and tranquility. Very nice open kitchen looking out into the bay. It really is a nice getaway and an environment to take a break and recharge the senses. Enjoy!

Indoor spacesFamilyValue

Guest suite in Fire Island

The cabin's entrance is framed by lush greenery and flowering plants. A wooden walkway leads to the door, and a small set of steps offers access. The rustic exterior features dark wood siding and a window for natural light.

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

FamilyKitchenCondition

4.97 out of 5 average rating, 116 reviews

4.98 out of 5 average rating, 243 reviews

An expansive deck offers a view of the Great South Bay, with a mix of comfortable seating options, including lounge chairs and a sectional sofa. The area is complemented by manicured green grass and a wooden railing, providing a serene backdrop for outdoor relaxation.

Home in Shirley

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

KitchenIndoor spacesCheckout

The living area features two dark blue sofas facing a wooden coffee table, with a media console displaying a television and decorative items. Light enters through multiple windows, highlighting the high, wooden ceiling and warm hardwood flooring.

4.97 out of 5 average rating, 34 reviews

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)

Indoor spacesFamilyHospitality

4.88 out of 5 average rating, 109 reviews

A spacious deck offers a panoramic view of the beach and water, with sunlight reflecting off the surface. Colorful chairs are positioned for relaxation, while shadows created by the railing add depth to the scene. The sandy shore can be seen in the distance.

Cottage in Milford

Cheerful 3 Bedroom Cottage with Fire Place

We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.

Indoor spacesFamilySleep quality

4.93 out of 5 average rating, 138 reviews

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

Home in Mattituck

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.

Indoor spacesFamilyBeach

4.89 out of 5 average rating, 159 reviews

Home in Bellport

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.

Indoor spacesFamilyAccuracy

4.98 out of 5 average rating, 184 reviews

A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.

Cottage in Riverhead

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.

Indoor spacesFamilyQuiet

4.9 out of 5 average rating, 177 reviews

An outdoor deck is seen featuring a spacious octagonal hot tub. It overlooks a calm canal bordered by green grass and trees. Nearby boats are docked, and the tranquil water reflects the clear sky, creating a peaceful atmosphere.

Home in Oakdale

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.

Indoor spacesKitchenTV

4.98 out of 5 average rating, 57 reviews

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!

FamilyIndoor spacesAccuracy

Popular amenities for Fire Island family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 156 reviews

A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

Home in Hampton Bays

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

KitchenIndoor spacesOutdoor spaces

4.87 out of 5 average rating, 141 reviews

A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

Indoor spacesKitchenValue

4.95 out of 5 average rating, 211 reviews

A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

Cottage in Guilford

Luxury cottage by the sea with hot tub and pool

FamilyIndoor spacesPool

4.89 out of 5 average rating, 140 reviews

An expansive ocean view is showcased from the studio, featuring calm waters that reflect the sunlight. Soft waves gently lap at the sandy shore, while lush greenery lines the foreground, contrasting with the clear blue sky above.

Apartment in Montauk

Ocean View Studio with King Bed

Indoor spacesKitchenBathroom

4.94 out of 5 average rating, 118 reviews

A spacious backyard is showcased with a large saltwater pool, featuring a floating inflatable and sun loungers arranged along the edge. The house stands in the background, framed by trees and an inviting grassy area, enclosed by a black fence.

Home in Hampton Bays

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

FamilyKitchenPool

4.93 out of 5 average rating, 158 reviews

A patio is shown with a wooden table and a dark wicker chair overlooking a scenic view. A clear sky with scattered clouds is visible in the background, along with open fields and distant structures. Utility poles line the road, adding context to the setting.

Home in Patchogue

Joyful Beach House, viewing The Great South Bay

KitchenIndoor spacesCheck-in

Home in Westhampton Beach

A contemporary home with large windows overlooks a serene pool area. Lush greenery surrounds the property, providing a natural backdrop. Sun loungers are positioned beside the pool on spacious stone decking, inviting relaxation and outdoor enjoyment.

Hamptons Oasis: pool, grill, lush landscape

Indoor spacesKitchenNearby

4.95 out of 5 average rating, 146 reviews

4.98 out of 5 average rating, 103 reviews

A warm wooden interior is featured, with wall art depicting horses and rural scenes. A rustic wooden table is positioned near the window, and a candle sits at its center. A potted plant adds a touch of greenery beside a cozy armchair.

Farm stay in Redding

Charming Historic Cottage in the Redwoods

Indoor spacesKitchenCheck-in

Family-friendly home rentals with air conditioning

4.99 out of 5 average rating, 112 reviews

The exterior of a charming cottage displays a white facade with dark blue trim and a welcoming front door. A well-manicured lawn featuring stepping stones leads up to the porch, surrounded by colorful flower beds and greenery.

Home in Patchogue

Hamptons Style Cottage close to everything!

FamilyIndoor spacesValue

5.0 out of 5 average rating, 4 reviews

Private Cherry Grove Home with Saltwater Pool

Indoor spacesAmenitiesBeach

A charming beach cottage exterior is visible, featuring a welcoming front porch with large windows and an American flag displayed. A brick pathway leads to the entrance, while colorful potted plants add a touch of greenery. Bicycles can be seen in the background.

4.93 out of 5 average rating, 27 reviews

New Listing-The Big Fish

Indoor spacesKitchenBathroom

A wooden deck extends toward a multi-level home set amidst lush greenery. Stairs lead to the entrance, which features railings and a large window, surrounded by trees and grass, contributing to a natural setting.

5.0 out of 5 average rating, 50 reviews

Fair Harbor, Fire Island sunny 3 bedroom

KitchenFamilyBiking

The image captures a sandy beach area bordered by lush grass, leading to two nearby wooden houses. A sunset sky illuminates the scene with soft hues, while the water gently reflects the changing colors. Relaxation and coastal charm are evident in this serene setting.

4.87 out of 5 average rating, 62 reviews

Bay Front Upper Level Cottage 47E

FamilyKitchenLocation

A spacious wooden deck features a lounge chair in green fabric, positioned under the shade of a large tree. Bamboo borders the area, enhancing the natural surroundings. A small table and additional seating can be seen nearby, creating a cozy outdoor retreat.

4.96 out of 5 average rating, 93 reviews

Secluded oasis close to everything!

Indoor spacesKitchenWalkability

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

Indoor spacesFamilyBackyard

5.0 out of 5 average rating, 4 reviews

Fire Island Beach House

FamilyBikingBeach

Family-friendly home rentals with Wifi

4.85 out of 5 average rating, 74 reviews

45 Broadway Fair Harbor.

KitchenFamilyNearby

An aerial view captures a circular rooftop deck surrounded by sandy pathways and neighboring houses. The beach is visible nearby, with the ocean stretching into the horizon, creating a serene coastal atmosphere. Green shrubbery is seen offering a touch of nature around the homes.

4.73 out of 5 average rating, 33 reviews

RoundHouse Fair Harbor

FamilyKitchenCleanliness

4.96 out of 5 average rating, 90 reviews

A well-maintained outdoor area features two blue lounge chairs facing a sandy beach. Pathways of stepping stones lead towards the water, framed by green grass and beach access. A gazebo is positioned nearby, complementing the serene coastal view.

Cottage in Patchogue

Toes in the Sand Beach Cottage

Indoor spacesFamilyCondition

A modern kitchen is equipped with sleek cabinetry and a large island featuring four white stools. Pendant lights hang overhead, illuminating the counter space. A window offers a view of the outdoor deck, enhancing the bright, open feel of the room.

4.92 out of 5 average rating, 13 reviews

Michigan Ave

KitchenFamilyCondition

4.94 out of 5 average rating, 87 reviews

A white yacht is anchored in calm waters, featuring a sleek design and a spacious deck. Surrounding greenery and a wooden dock complement the serene maritime setting. A second yacht is visible in the background, enhancing the scene of nautical tranquility.

Boat in Fire Island

Classic Yacht in the Fire Island Pines

Indoor spacesKitchenDecor

The exterior of a green cottage features a white picket fence and neatly trimmed hedges. An American flag is displayed from the porch, where a door with a decorative window adds character. Large windows allow natural light to brighten the space.

4.89 out of 5 average rating, 19 reviews

Beach and Town House Steps to ALL!

FamilyIndoor spacesHospitality

5.0 out of 5 average rating, 9 reviews

Gatsby's -Sky Level w/Pool- Sleeps 12

KitchenFamilyWalkability

A spacious deck features new outdoor furniture, including a sectional sofa, lounge chairs, and a dining table shaded by a large umbrella. A BBQ grill is positioned nearby, surrounded by lush greenery, enhancing the outdoor ambiance.