Vacation rentals in Long Island

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Top-rated vacation rentals in Long Island

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Top guest favorite

An outdoor dining area is set with a wooden table and benches, overlooking a grassy expanse leading to the water. Plates and utensils are neatly arranged on the table. Surrounding the area, shrubs and small plants complement the serene coastal view under a clear blue sky.

Cottage in Riverhead

4.97 out of 5 average rating, 156 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.

Guest favorite

The interior of the cabin features a spacious bed framed by large windows that invite natural light. A small dining table is set beside a plant, and the wooden ceiling enhances the cozy ambiance. A decorative blanket adds a splash of color to the bed.

Cabin in Montauk

4.96 out of 5 average rating, 469 reviews

Tiny Cottage in Hither Woods, Montauk

A little cabin on our property in Hither Woods. A cozy hideaway conveniently located 12 minutes walk from Gurney's Beach Resort, 16 minute walk from public path to beach, and 6 minutes drive from Montauk town for restaurants and nightlife. Good for couples and solo adventurers, the space is private and homey, with outdoor shower and Chimenea fire pit. The main house is 65ft away, but we honor your privacy. The cottage comes with WiFi, window A/C and complimentary coffee or tea. Parking for 1 car

Guest favorite

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

4.98 out of 5 average rating, 206 reviews

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

Guest favorite

A modern kitchen features white cabinetry and sleek stainless steel appliances. The spacious layout includes a large refrigerator, a built-in oven, and a dishwasher. Natural light enters through nearby windows, illuminating the stylish countertops and a decorative rug that adds warmth to the space.

Apartment in Stamford

4.97 out of 5 average rating, 104 reviews

Luxurious 1BR Downtown Stamford

Step into your luxurious haven in the heart of downtown Stamford, where opulence seamlessly meets comfort and indulgence becomes your personal mantra. From the impeccable design and luxurious amenities to the prime location, every moment spent here is a celebration of the finer things in life. Treat yourself to an extraordinary stay, crafting memories that will linger in your heart for a lifetime . Welcome to a world where luxury knows no bounds, and warm hospitality eagerly awaits your arrival

Guest favorite

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

4.96 out of 5 average rating, 252 reviews

Midcentury Modern ZenHouse Sculptor Studio

Mid-century modern historic private estate surrounded by river @Zenhouse_satori and main house. Great for memorable romantic getaway, photoshoots and film locations! ZENHOUSE mission is rooted in the values of respect, creativity, and excellence. Inspired by the timeless principles of Zen, we offer a luxurious and exclusive experience where tranquility blends with art, spirituality, and nature. We provide a serene environment and personalized service to awaken your true nature and find Zen

Guest favorite

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

4.96 out of 5 average rating, 226 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Guest favorite

A bright yellow door with a window covered by blinds is framed by gray shingles. Two exterior lamps are mounted on either side, and a small porch area features a decorative mat in front of the door.

Guest suite in Wading River

4.91 out of 5 average rating, 274 reviews

Beachy En Suite /Gateway to The North Fork

Adorable,quiet,clean, w private entrance, private bedroom and bathroom,breakfast nook and patio.We are located in a beach front town dubbed“Gateway to the North Fork”.Walking/driving directions to local beaches,15minute walk to our community beach,Wildwood StPk(.6mi away).Niks deli nearby.Minutes by car to wineries,breweries,farm stands,EastWind,TangerOutlets15min away,35min to Hamptons,Greenport!Hosts live in adjoining house.NoTV but Wifi is good so bring your device for entertainment.

Top guest favorite

A well-lit bedroom features a spacious bed with decorative bedding, positioned against a soft blue wall. Natural light enters through large windows, adorned with sheer curtains. A compact dresser stands nearby, and an elegant table lamp adds functionality to the cozy space.

Home in Holbrook

4.9 out of 5 average rating, 284 reviews

Cozy studio

We are 10 minutes away to MacArthur Airport in Islip, 5 minutes to shopping center where you can find supermarkets, restaurants, and stores. We are 10 minutes away from LIRR train station where you can get a ride to Manhattan. Although the studio is centrally located a car or Uber is recommended,. You'll have your own bathroom, kitchen with microwave, coffee maker, toaster, fridge, air conditioner, tv with cable and internet. Our study is a FREE SMOKING PLACE! Not smoking or vaping!

Top guest favorite

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

4.97 out of 5 average rating, 146 reviews

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

Guest favorite

A side view of the guest suite reveals a private entrance with a white door and small steps leading up to it. A winding stone walkway is bordered by grass and gardens, providing access to the suite in a serene outdoor setting.

Guest suite in Bay Shore

4.95 out of 5 average rating, 276 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.

Guest favorite

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 Mattituck

4.93 out of 5 average rating, 136 reviews

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.

Top guest favorite

A bright bedroom features a spacious bed with a white, textured duvet cover and a decorative yellow pillow. Natural light streams in through a window adorned with yellow and dark curtains. A nightstand and a chair accompany the bed, enhancing the room's functionality.

Apartment in Massapequa

4.97 out of 5 average rating, 107 reviews

Cozy Getaway Retreat /South Shore/ NYC 40min

Cozy, non-smoking 2BR apartment in a Hi-Ranch home—private 1st floor walk-in (not a basement). Clean, modern, and perfect for 2–4 guests. 🛏️ Max 4 guests. Family lives upstairs—please be respectful. 📵 No smoking, 🆔 Valid photo ID required to book& at check in. If inviting others, add them to your reservation when booking. Enjoy a peaceful and convenient getaway! Book your staycation today and create lasting memories.

Vacation rentals for every style

Get the amount of space that is right for you

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Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Long Island vacation rentals

Monthly stays

Free parking on premises

Self check-in

Pool

Gym

Long Island home rentals

Top guest favorite

A modern kitchen features sleek white cabinetry and a spacious island with a built-in microwave. Warm tones are added by woven light fixtures above, complemented by a comfortable seating area visible in the background. Natural light filters through the window, enhancing the welcoming ambiance.

Home in Long Beach

4.99 out of 5 average rating, 143 reviews

Boho Beach House

Top guest favorite

A view of the exterior of the property is framed by lush greenery, featuring a stone wall with a potted plant. Beyond, expansive views of the lake and surrounding mountains are visible beneath a clear sky.

Home in Greenwood Lake

4.99 out of 5 average rating, 185 reviews

Spectacular Lake Views from Every Room & Garden

Guest favorite

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

4.96 out of 5 average rating, 111 reviews

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

Guest favorite

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

4.94 out of 5 average rating, 155 reviews

The Harbor House: Beachfront Home 1 hour from NYC

Guest favorite

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.

Home in Cold Spring Harbor

4.97 out of 5 average rating, 107 reviews

Captain’s Cottage Water Views -3 Bdrm

Guest favorite

The living area features two comfortable gray sofas arranged around a round coffee table with a decorative centerpiece. A large TV is mounted on the wall opposite, while natural light filters in through the window adorned with decorative plants.

Home in Huntington Station

4.92 out of 5 average rating, 229 reviews

THE OASIS @ LONG ISLAND

Guest favorite

A private heated pool is surrounded by a wooden deck, featuring two red lounge chairs. Volleyball nets are set up across the pool, which is framed by lush greenery and a large umbrella providing shade. Clear blue water reflects the bright sky.

Home in Commack

4.99 out of 5 average rating, 143 reviews

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

Guest favorite

A bright living room features a comfortable gray sofa against a neutral wall, complemented by a light-colored rug with geometric patterns. A wooden coffee table sits in front, with a lounge chair nearby. Natural light enters through multiple windows, creating a spacious feel.

Home in Greenport

4.95 out of 5 average rating, 360 reviews

The Sandpiper

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Vacation rentals with pools in Long Island

Guest favorite

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

4.93 out of 5 average rating, 127 reviews

Joyful Beach House, viewing The Great South Bay

Top guest favorite

Home in Cutchogue

4.97 out of 5 average rating, 206 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Guest favorite

The outdoor area features a spacious pool surrounded by a neat stone patio. Lounge chairs are arranged neatly by the water, while lush greenery and mature trees provide shade and privacy. A sunlit house with large windows is visible in the background.

Home in Westhampton Beach

4.92 out of 5 average rating, 104 reviews

Hamptons Oasis: pool, grill, lush landscape

Top guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 192 reviews

Secluded Southampton Cottage w/Pool & Spa

Guest favorite

An aerial view captures a spacious backyard featuring a heated saltwater swimming pool surrounded by lounge chairs. The meticulously maintained lawn is dotted with trees and flowering plants, leading to a paved pathway. A deck with outdoor seating and an umbrella creates inviting outdoor spaces.

Home in Manorville

4.97 out of 5 average rating, 259 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Guest favorite

A private swimming pool is surrounded by lush greenery, featuring landscaped areas with various plants. The pool's clear blue water reflects the sunlight, while the patio area is paved with bricks. A safety fence encloses the pool for added security.

Home in Port Jefferson

4.92 out of 5 average rating, 125 reviews

Port Jefferson Convenient, Cozy and Chic!

Top guest favorite

A spacious outdoor pool is surrounded by a stone patio, featuring a pink flamingo floatie. Aqua-colored lounge chairs are positioned nearby on a gravel surface, with greenery and trees framing the area for privacy.

Home in Hampton Bays

4.98 out of 5 average rating, 130 reviews

Beach House Feel - newly renovated backyard Oasis

Guest favorite

A spacious pool area features a crystal-clear swimming pool surrounded by a wooden deck. Colorful sun loungers are arranged neatly, accompanied by large umbrellas offering shade. Lush greenery is visible in the background, enhancing the tranquil outdoor setting.

Home in East Hampton

4.93 out of 5 average rating, 155 reviews

Large heated pool, games room, near private beach

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Home rentals with pools in Long Island

Top guest favorite

A patio area is shown, featuring a round table and colorful chairs. In the background, a sunlit lawn is dotted with trees, leading to a spacious pool area. A seating arrangement with cushions invites relaxation, surrounded by lush greenery.

Home in Cutchogue

5 out of 5 average rating, 38 reviews

North Fork paradise between beaches and vineyards

Top guest favorite

Home in Southampton

4.96 out of 5 average rating, 45 reviews

Spectacular Southampton Retreat!

Top guest favorite

An aerial view captures the heated saltwater pool surrounded by a spacious patio. Lounge chairs and shaded seating areas are arranged near the pool, with outdoor furniture positioned for relaxation. Lush greenery and a landscaped garden frame the space, providing a serene environment.

Home in Yaphank

5 out of 5 average rating, 37 reviews

Long Island Getaway w/ Heated Pool & Lake

Guest favorite

The exterior of the home presents a charming shingle-style design, featuring multiple large windows. A spacious patio with outdoor seating surrounds a clear blue pool, complemented by a large umbrella for shade. Lush greenery provides privacy along the property line.

Home in Southampton

5 out of 5 average rating, 47 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Guest favorite

An outdoor patio features multiple wooden lounge chairs arranged around a central fire pit. A gunite pool with clear water reflects the surrounding greenery. The main house, visible in the background, showcases a classic design with white siding and large windows.

Home in Sag Harbor

4.86 out of 5 average rating, 270 reviews

Exclusive Sag Harbor Compound

Top guest favorite

Home in Bellport

5 out of 5 average rating, 28 reviews

Monkey Puzzle - Renovated Cottage in Bellport

Superhost

A spacious outdoor area features a clean blue pool surrounded by lounge chairs. The three-story yellow house, with a modern design, showcases multiple balconies that overlook the pool, providing natural light and views of the garden.

Home in Southampton

4.88 out of 5 average rating, 50 reviews

Summer Getaway in the Hamptons. Mins from Beaches

Top guest favorite

A serene backyard showcases a sparkling swimming pool surrounded by lush greenery. Comfortable seating is arranged near the poolside, and a large umbrella provides shade. The inviting space is designed for relaxation and enjoyment.

Home in Eastport

5 out of 5 average rating, 14 reviews

Extravagant Eastport Retrieve

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Your guide to Long Island

Welcome to Long Island

To the east of New York City, Long Island stretches from just past John F. Kennedy International Airport all the way to Montauk, and has a personality all of its own. At its heart, it’s a comfortable suburb so many New Yorkers call home, but it’s just as vibrant of a destination, especially thanks to its 118 miles of white-sand coastline with 150 beaches on both sides. It also has its own wineries and breweries, more than 60 golf courses, art and science museums, historic landmarks, and the fanciest of mansions along its Gold Coast. And with fresh seafood and farms of every kind, the food scene is just as thrilling.

The best time to stay in a vacation rental in Long Island

The warmest months in Long Island are from May to September, and the coldest are between December and February. While it does snow during the winter months, it tends to be less than the rest of the state — usually just a few snowstorms a year, and most times, it’s less than an inch. Annual events include the oldest Triple Crown race, the Belmont Stakes, in Elmont in June; the Tomato Festival in Mattituck in August; the Long Island Summer Festival at Smith Haven Mall in Lake Grove in July; and the Festival of Trees at the Cradle of Aviation Museum in Garden City during the holidays.

Top things to do in Long Island

Fire Island

No cars are allowed on this 32-mile-long barrier island along the Atlantic coast, inherently making it an idyllic beach destination where the pace of life slows down. Along with its 17 separate communities is the 40-acre maritime Sunken Forest and 168-foot-tall Fire Island Lighthouse — the tallest on Long Island.

Gold Coast Mansions

All that glitters just might be gold here. On the northern side of Long Island from Port Washington to Centerport, the coastline is dotted with mansions so extravagant that they’ve inspired literature. Highlights include the Vanderbilt Museum and Planetarium in Centerport.

Montauk Point State Park

At the far eastern point of the South Fork, the waters of the Atlantic Ocean meet the strait of the Block Island Sound, causing a phenomenon where the tides seem to race against one another. Take a hike along the shore and you might also see seals out on the rocks, or grab a board and surf the waves (surf fishing is also popular here). For a higher perspective, stop by the state’s oldest lighthouse, Montauk Lighthouse, right next door.

Vacation rentals in Long Island

Top-rated vacation rentals in Long Island

Vacation rentals for every style

Popular amenities for Long Island vacation rentals

Long Island home rentals

Vacation rentals with pools in Long Island

Home rentals with pools in Long Island

Your guide to Long Island

Welcome to Long Island

The best time to stay in a vacation rental in Long Island

Top things to do in Long Island

Fire Island

Gold Coast Mansions

Montauk Point State Park

Destinations to explore