Waterfront holiday rentals in Fire Island

4.95 out of 5 average rating, 189 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

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Home in Cold Spring Harbor

A serene waterfront scene captures several boats anchored in calm waters, with a backdrop of trees showcasing autumn foliage. Vintage and modern homes are visible along the shore, creating a picturesque town ambiance along the shoreline.

4.98 out of 5 average rating, 123 reviews

Captain’s Cottage Water Views -3 Bdrm

Enjoy this this light and airy home with spectacular sunset & water views. 5 minute drive to private beach. Oversized deck and 2 porches all with water views. Located in idyllic, historic Cold Spring Harbor. Explore the green belt with access from rear yard. Walk to shopping, restaurants, live music, fishing or picnic in the local park. Sip a glass wine & enjoy the beautiful sunsets from the expansive deck with firepit. Upstairs loft bedroom has a fireplace & private deck w/ water view.

4.98 out of 5 average rating, 225 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, 104 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, 606 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.

Apartment 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!

4.98 out of 5 average rating, 167 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 North Fork

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.

4.97 out of 5 average rating, 183 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, 118 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.

Guesthouse in Waccabuc

French Guest House in Waccabuc

A mini Versailles just outside of NYC - located on a private and gated eight acre estate with its own lake in Waccabuc, NY. Surrounded by 18C statuary, manicured gardens and fountains, it’s equivalent to staying in a 5-Star European luxury hotel suite (house designed by David Easton) with its heated stone floors and heated towel rack, luxury linens, gold taps and serene private entrance. (.7mi from Waccabuc Country Club, 60 min from NYC by car or train - Katonah train St)

4.93 out of 5 average rating, 150 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

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

4.91 out of 5 average rating, 171 reviews

The kitchen is designed with white cabinetry and stainless-steel appliances, including a refrigerator and gas stove. A large island with seating is positioned across from the sink, illuminated by natural light from nearby windows. Hardwood flooring adds warmth to the space.

Home in Bay Shore

The Harbor House

Beautiful three bedroom home located on the waterfront in Bay Shore’s historic bay district. Steps to local waterfront restaurants and marina. Short walk to Main Street shopping, restaurants and nightlife and just minutes from the Fire Island Ferries and Long Island Railroad. Amenities include fully stocked kitchen, large deck for barbecuing with harbor views, natural wood fire pit with Adirondack chairs and fully fenced in yard.

4.85 out of 5 average rating, 211 reviews

A wooden dock extends into the water, lined with boats gently bobbing on the surface. Lush green hills rise in the background, while a clear blue sky with scattered clouds frames the scene. People are gathered along the dock, enjoying the views.

Apartment in Northport

Harbor Studio - Across from historic Northport doc

Across the street from historic Northport dock and the beautiful town park, this downtown studio is walking distance to everything. Drive or boat in to town and have a lovely convenient place to stay close to everything. Dining, shopping, the park, and the Famous Engleman theater. The studio has a private entrance, full kitchen, and bath with shower and tub. Enjoy a night, weekend, or whole week in historic Northport Village.

Popular amenities for Fire Island waterfront rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

4.97 out of 5 average rating, 32 reviews

A bright studio space is occupied by a spacious bed adorned with various green cushions. A kitchenette with modern appliances, including a microwave, is visible in the corner. Natural light filters through the windows, highlighting the decorative elements on the walls and floor.

Apartment in Branford

Stony Crk Studio ideal for trvl nurses…

Apartment in Rockaway Beach

A bright living space features a comfortable orange sofa, a sleek coffee table, and a flat-screen television. Decorative artwork adorns the walls, complemented by a dining area with a wooden table and chairs. A Christmas tree adds a festive touch to the corner.

4.81 out of 5 average rating, 287 reviews

Beachfront apartment with ocean view and huge deck

4.99 out of 5 average rating, 155 reviews

The bedroom features a queen bed with a colorful marine-themed bedding set. Light blue walls complement the natural wood flooring. Two windows allow ample natural light, with blinds for privacy. Decorative elements include beach-themed art, a nightstand, and a dresser.

Apartment in Northport

Amazing one bdrm flat at the beach!

5 out of 5 average rating, 67 reviews

An aerial view captures the peaceful Great South Bay area, showcasing a residential neighborhood with various boats and docks along the canal. A mix of homes and buildings line the streets, surrounded by lush greenery, contributing to the serene coastal atmosphere.

Apartment in Bay Shore

Turtle Dove Cozy Gem on the Bay

4.94 out of 5 average rating, 53 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.

Apartment in Stamford

Spacious. Water Views & Access. Steps to Beach.

4.79 out of 5 average rating, 344 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.

Apartment in North Fork

Amazing Greenport Village Apartment in CENTER!

Apartment 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, 488 reviews

Fair Haven Heights Entire 1 Bedroom Apartment

4.98 out of 5 average rating, 130 reviews

Apartment in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

Waterfront house rentals

4.82 out of 5 average rating, 107 reviews

A spacious outdoor deck area is visible, leading to a sandy beach. The house features large windows on the upper level, allowing natural light to fill the interior. Surrounding buildings include a mix of colors and styles, contributing to the residential atmosphere.

Home in Milford

Beachfront house on Long Island Sound

4.8 out of 5 average rating, 359 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

4.96 out of 5 average rating, 48 reviews

A serene waterfront scene is presented, showcasing calm blue waters extending towards the horizon under a clear sky sprinkled with a few clouds. The sandy shoreline gently curves along the edge, bordered by sparse greenery for a peaceful coastal ambiance.

Home in Mastic Beach

Mastic Beach Surf House

4.94 out of 5 average rating, 113 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, 261 reviews

A spacious outdoor pool is surrounded by natural greenery, featuring a stone patio and a diving board. A covered lounge area with large windows overlooks the pool, providing a serene setting for relaxation and leisure.

Home in Stamford

Midcentury Modern ZenHouse Sculptor Studio

5 out of 5 average rating, 116 reviews

An aerial view captures the coastal neighborhood, with a sandy beach and clear blue water. The vibrant homes line the shore, featuring varied architectural styles. Lush greenery borders the area, enhancing the sense of tranquility and charm typical of beachside living.

Home in Milford

Steps2Beach, Fish Pond, Tropical Backyard Oasis!

4.95 out of 5 average rating, 248 reviews

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

Home in The Hamptons

Private beach, fully updated house, on 2 acres.

5 out of 5 average rating, 108 reviews

A view of Long Island Sound at sunset is captured from the balcony. Gentle waves reflect the colors of the sky, ranging from soft pink to deep orange, while Charles Island is visible in the distance, framed by the serene horizon.

Home in Milford

Milford Beach House - Newer Construction!

Waterfront condo accommodation

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.

4.87 out of 5 average rating, 126 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, 156 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.

Condo 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.

Condo in Freeport

4.55 out of 5 average rating, 77 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, 172 reviews

Beautiful Waterview Condo on the North Fork of LI

A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.

4.88 out of 5 average rating, 154 reviews

Waterfront Autumn Escape in Wine Country: 2BR

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.

4.91 out of 5 average rating, 149 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

The living area features a comfortable seating arrangement with a dark couch and light-colored accent chairs. A dining table sits nearby, accompanied by additional seating. Large windows offer natural light, with greenery visible outside. A flat-screen TV and decorative mirror add to the space.