Family-friendly holiday rentals in Fire Island

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Top-rated family-friendly rentals in Fire Island

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Guest favourite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, 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. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

11–18 Jan

$1,015 SGD per night

Guest favourite

Guest suite in Fairfield

4.92 out of 5 average rating, 112 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

3–10 Apr

$160 SGD per night

Guest favourite

Home in Shirley

4.98 out of 5 average rating, 178 reviews

Luxurious Waterfront Beachouse 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

11–18 Sep

$708 SGD per night

Guest favourite

Home in Oakdale

4.85 out of 5 average rating, 122 reviews

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.

16–23 Sep

$792 SGD per night

Superhost

Guest suite in Piermont

4.85 out of 5 average rating, 381 reviews

Cozy private apartment with Hudson River views

This cozy apartment just one block from the Hudson River, is on the ground level of a house, with a separate entrance offering complete privacy. This modern space has a fully equipped kitchen, beautiful bathroom, comfy queen bed, reading chair, books galore, and a desk. Located in the adorable town of Piermont, it has the feel of a country retreat, a waterfront town, and it's an easy commute to Manhattan. As of Nov. 2022, the WIFI has been upgraded and it is now RELIABLE & HIGH-SPEED.

24–31 May

$160 SGD per night

Guest favourite

Guest suite in Bay Shore

4.95 out of 5 average rating, 240 reviews

Bay Shore's Private Guest Suite

Welcome to our cozy guest suite nestled within walking distance of the Fire Island ferries and conveniently close to local amenities! This private unit, attached to the main part of our home, offers a comfortable retreat for your stay. Step through your own private entrance into a welcoming living room, where you can unwind after a day of exploration. The bedroom features a queen-sized bed, providing a restful night's sleep, and an adjoining bathroom offers convenience and privacy.

21–28 May

$250 SGD per night

Guest favourite

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!

3–10 May

$163 SGD per night

Guest favourite

Flat in Islip Terrace

4.87 out of 5 average rating, 175 reviews

PHILS COZY Private studio(new kitchen/fresh paint)

My place is close to restaurants and dining, the beach, and family-friendly activities. You’ll love my place because of light, comfy bed, the kitchen, the coziness, and the high ceilings and privacy. Good for couples, solo, business travelers, and furry friends (pets). Located near the airport and train station. I ESPECIALLY PREFER MONTHLY OR SEASONAL LENGTHY VISITORS.

11–18 Feb

$128 SGD per night

Guest favourite

Guest suite in New Haven

4.99 out of 5 average rating, 157 reviews

Cozy cottage in historic neighborhood

Housed in a 100-year-old building nestled between the Victorian houses in New Haven's historic City Point neighborhood, once the center of New England's oyster trade, our cottage is a two-block walk from the marina (and its award-winning restaurant), a 10 minute-drive from the West Haven beaches and a few minutes' drive to Yale.

2–9 Jun

$204 SGD per night

Guest favourite

Home in Ronkonkoma

4.86 out of 5 average rating, 147 reviews

Convenient home in Ronkonkoma

Charming cape that is completely private. This is not an apartment within a house. The entire home and yard are yours to enjoy with complete privacy. Conveniently located 6 blocks from LIRR Ronkonkoma Station, 2 miles from Islip MacArthur Airport, and 1 mile from Long Island Expressway. 5.5% Occupancy Tax included.

5–12 Jun

$157 SGD per night

Guest favourite

Guest suite in Lake Ronkonkoma

4.99 out of 5 average rating, 235 reviews

Private New Apartment

Open concept living. Cathedral ceilings. 1 Bedroom, Full Bath. Private parking. Patio. 5 minutes from train, 15 minutes to MacArthur Airport. Close to Stony Brook, South shore ocean beaches, and the north shore of Long Island. Perfect if you are planning on heading out east to the wineries!

28 Mar – 4 Apr

$273 SGD per night

Guest favourite

Guest suite in Patchogue

4.93 out of 5 average rating, 267 reviews

Shores Retreat Suite - Peaceful Relaxation

Enjoy your own private, spotlessly clean SUITE midway between NYC & the Hamptons. Shores Retreat is the place for relaxation, revitalization & free kayaking or canoeing in a spa like atmosphere. Shores Retreat is the perfect romantic escape or family getaway!

18–25 Jul

$256 SGD per night