Waterfront holiday rentals in Fire Island

4.98 out of 5 average rating, 226 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

4.88 out of 5 average rating, 114 reviews

Home in The Hamptons

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

4.97 out of 5 average rating, 612 reviews

An expansive patio extends towards the shimmering waters of Long Island Sound, featuring lounge chairs and a dining table with an umbrella. Decorative planters and lanterns are arranged along the patio edge, complementing the serene waterfront view.

Flat in Milford

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

4.93 out of 5 average rating, 169 reviews

A serene waterfront view is presented, showcasing calm waters reflecting a soft pink sky. Lush green grasses frame the foreground, while a tree line marks the horizon, creating a tranquil landscape. A few ducks can be seen gently floating on the water.

Loft in Milford

Lovely water front lower-level loft, free parking

This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

4.85 out of 5 average rating, 188 reviews

A spacious living area features large glass windows that frame a stunning sunset over the water. The open design enhances natural light, illuminating the room's elegant furnishings and wooden accents. A dining table is positioned near the windows, inviting relaxed meals with a view.

Cabin in Shirley

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

4.85 out of 5 average rating, 127 reviews

A cozy studio features a comfortable bed adorned with floral bedding and soft pillows. A modern chair and side table complement the space. Light is provided by a bedside lamp, and the room is accented with turquoise curtains and a decorative mirror on the wall.

Flat in Freeport

Eleg B&B Stu Apt steps frm Nautical Mile

-Pvt Studio -Special Occassion Decor -Bkfst: pcakes, waffles, Jimmy Dean -Mr. Cool A/C & Ht Pmp -Fireplace -Recliner/pull-out bed, -Bkfst bar, -Kitchenette -Kurig Mach -Elec Kettle -Mwave -Refrige -Toaster -Jet Blndr -Iron, Iron Bd, hangers, (Hallway closet) -Hair Dryer (Hlwy clst) -WiFi -Wht Noise Mach -PS4, Fire Stick, -Ergo Chr, Dsk, Mse, Mntr, Keybrd -50 Inch smt tv, -Bosch hot water, -5 min walk to Nautical Mile <40min train to Mhttn/JFK -Jones bch -Wstbry Mall -UBS Stadm -Eshr Pk

4.94 out of 5 average rating, 130 reviews

A calm waterfront scene features a vibrant sailboat gliding across the bay, surrounded by green marshland. A wooden dock leads into the water, with several colorful chairs positioned for relaxation. Soft hills and houses line the distant shore under a gentle mist.

Home in Mastic Beach

Gorgeous Waterfront and Indoor Pool Family Oasis!

Breathtaking Waterfront home with 37 foot heated indoor pool. 3 Bedrooms plus a 800 Sq/Ft master bedroom with wood burning fireplace. WiFi, 3rd floor entertainment room with 120 inch screen movie projector, karaoke, fooseball, pool table. Wraparound terrace, sunroom, 45ft dock with launching ramp, putting green, sand trap, outdoor kitchen, bar & stone patio with tables & BBQ grills & fire pit. Ability to catch abundant fish & blue crabs right from the dock. Picture tells a thousand words.

4.93 out of 5 average rating, 139 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

Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

4.96 out of 5 average rating, 489 reviews

A serene view of the Hudson River at sunset, featuring vibrant orange and yellow hues reflected on the calm water. Silhouettes of trees outline the scene, creating a peaceful atmosphere with the distant hills visible against the colorful sky.

Flat in Ossining

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

4.97 out of 5 average rating, 194 reviews

A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

4.99 out of 5 average rating, 107 reviews

An aerial view captures a cozy cottage surrounded by lush greenery, featuring large windows that glow warmly in the evening light. A stone patio is visible, with outdoor seating and a fire pit. Nearby, a well-maintained lawn and a parking area with vehicles can be seen.

Cottage in Guilford

Waterfront Joshua Cove Cottage with private beach.

Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

4.98 out of 5 average rating, 123 reviews

The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.

Guest house in Waccabuc

French Guest House in Waccabuc

A private, European-style retreat just 60 minutes from NYC. Set on an eight-acre gated French estate with its own lake, this guest house feels like a mini Versailles with 18th-century statuary, fountains and manicured gardens. Designed by David Easton, it features heated stone floors, a heated towel rack, luxury linens, gold fixtures, fast WiFi, and a private entrance. Minutes from Waccabuc Country Club and the Katonah train station.

Popular amenities for waterfront rentals in Fire Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.81 out of 5 average rating, 292 reviews

Flat in Rockaway Beach

Beachfront apartment with ocean view and huge deck

4.97 out of 5 average rating, 244 reviews

A scenic view of a marina features a vibrant shipyard with a large vessel under construction, surrounded by historic buildings and greenery. Two pedestrians stroll along a path by the water, while power lines are visible above, adding to the coastal atmosphere.

Flat in Stonington

Mystic River Getaway - Walk To Downtown & Seaport!

5 out of 5 average rating, 17 reviews

A cozy bedroom is presented with wooden beam ceilings and light blue walls. A spacious bed is adorned with patterned pillows and a black and white striped blanket. A nightstand with a lamp is positioned beside the bed, while the edge of a modern kitchen is visible in the background.

Flat in Fire Island

One Bedroom Apt in Cherry Grove

4.93 out of 5 average rating, 123 reviews

A spacious living area features a comfortable sectional sofa facing a sleek coffee table. Natural light floods in through large windows, highlighting the polished wood floor. A modern kitchen with bar stools is visible in the background, creating an inviting open layout.

Flat in Stonington

Stevedore Landing-#3 · walk Mystic-Train/EV Lvl-2

4.86 out of 5 average rating, 102 reviews

A comfortable living area features a black sofa and a light-colored couch with decorative pillows. A wooden coffee table sits at the center, surrounded by a small dining table and chairs. Soft lighting is provided by a stylish fixture, and natural light enters through the windows.

Flat in South Norwalk

Water View SONO 2 Bedroom Walk to Metro & Dining

4.94 out of 5 average rating, 54 reviews

A spacious room features warm hardwood floors and large windows allowing natural light. A king size bed is adorned with light bedding and soft pillows. A comfortable sofa can be seen in the background, alongside a wooden coffee table and plants, fostering a relaxed atmosphere.

Flat in Stamford

Spacious. Water Views & Access. Steps to Beach.

4.79 out of 5 average rating, 345 reviews

A spacious living area showcases a light grey sectional sofa and a matching loveseat arranged around a wooden coffee table. A striped area rug adds a pop of color to the dark flooring. Shelves line the walls, and large windows allow natural light to fill the room.

Flat in North Fork

Amazing Greenport Village Apartment in CENTER!

Flat in Fair Haven Heights

Two Adirondack chairs are positioned by the water's edge, reflecting soft lights from distant boats on a calm evening. The still water mirrors the warm glow, creating a tranquil atmosphere. Nearby, a small fire pit adds warmth to the outdoor space, surrounded by lush greenery.

4.88 out of 5 average rating, 491 reviews

Fair Haven Heights Entire 1 Bedroom Apartment

Waterfront house rentals

4.8 out of 5 average rating, 365 reviews

A charming red cottage is set among lush greenery, showcasing a manicured lawn leading to the porch. The house features a rustic stone chimney and a welcoming front porch adorned with white railings. Nearby, a small structure complements the main home with a rounded window.

Home in Port Jefferson

The Hilltop Harborview

4.92 out of 5 average rating, 112 reviews

An aerial view captures a spacious lakefront property surrounded by lush greenery. Trees frame the yard, which gently slopes toward the water. The exterior of the house is clad in light gray, with multiple windows reflecting the natural surroundings. A patio area is visible near the water's edge.

Home in Putnam Valley

Crystal Wave LakeHouse

4.97 out of 5 average rating, 101 reviews

The kitchen features modern cabinetry with a contrasting dark granite island. Three cushioned stools are positioned at the island. Natural light enters through a window above the sink, illuminating new stainless steel appliances and a sleek backsplash. A door leads to the outdoor area.

Home in Black Rock

Cape on the Water

4.93 out of 5 average rating, 120 reviews

A wide view of a sandy beachfront stretches along the coastline, bordered by calm blue waters under a clear sky. Lush greenery can be seen in the distance, suggesting a nearby park or recreation area. Several individuals are spaced along the shore enjoying the beach.

Home in Waterford

Salty Breeze - Waterfront Cottage on the Cove

4.95 out of 5 average rating, 168 reviews

An inviting waterfront deck is displayed, featuring two lounge chairs with striped fabric and a small table. A fire pit sits nearby, surrounded by a clear view of the bay, where sailboats are gently anchored. Lush greenery lines the horizon, enhancing the serene atmosphere.

Home in Centerport

The Harbor House: Beachfront Home 1 hour from NYC

4.95 out of 5 average rating, 126 reviews

A two-story oceanfront home features a light gray exterior with large windows and a turquoise front door. A spacious ground level is accessible via white railings, leading to an outdoor sitting area. The serene beach and water views are visible in the background.

Home in Milford

Oceanfront Retreat with Hot Tub

4.92 out of 5 average rating, 154 reviews

A bright living area features light-colored walls and wooden flooring. A comfortable sofa and a plush chair are arranged around a rustic coffee table. A ceiling fan hangs above, while a kitchen with a blue island is visible in the background, enhancing the space's openness.

Home in North Fork

Modern Farmhouse Steps to Beach & Love Lane

4.97 out of 5 average rating, 205 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

Waterfront apartment rentals

A living area features shiplap walls and ample natural light from large windows. A dark sectional sofa is positioned next to a glass coffee table with a small plant. An open kitchen area is visible, along with access to a screened porch through sliding doors.

4.86 out of 5 average rating, 128 reviews

Beautiful condo on Long Islands Northfork

A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.

4.85 out of 5 average rating, 159 reviews

2 BR Waterfront Autumn Escape in Wine Country

4.92 out of 5 average rating, 38 reviews

A spacious living area is highlighted by exposed wooden beams and brick walls. Natural light streams through two large windows. Comfortable seating is provided by a leather couch facing a low coffee table. A wooden dining table with chairs sits in the corner, adding functionality.

Apartment in Long Beach

City style apartment, Beach Passes Included

A tranquil waterfront scene is captured at sunset, with the sky painted in shades of pink and purple. The calm water reflects the vibrant colors, creating a mirrored effect. A dock can be seen in the foreground, adding to the serene atmosphere of the setting.

Apartment in Freeport

4.51 out of 5 average rating, 78 reviews

Waterfront Zen - Private 2 Bedroom

The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.

4.9 out of 5 average rating, 174 reviews

Beautiful Waterview Condo on the North Fork of LI

A spacious sleeping area features a tufted white bed with dark bedding, complemented by two decorative pillows. A tall, framed mirror stands beside a clear side table. The wall behind is adorned with a patterned wallpaper, and warm wooden flooring adds to the inviting space.

Apartment in Yonkers

Hudson Valley Cottage Apartment

Apartment in The Hamptons

A modern kitchen space features stainless steel appliances and white cabinetry. A spacious island with a sink provides a functional area for meal preparation. Natural light floods the room, highlighting the dining area with a view of the water through sliding glass doors.

4.92 out of 5 average rating, 13 reviews

Condo on the Sound - Navy Beach

Two blue Adirondack chairs are positioned on a manicured lawn, facing a vibrant sunset over the ocean. The sky displays pink and orange hues as the sun sets on the horizon, creating a serene outdoor setting.