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Vacation rentals in Long Island

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Vacation rentals for every style

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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 spacious living area is highlighted by exposed wooden beams and a stone fireplace. A cozy seating arrangement includes a colorful blanket draped over a large sofa. Natural light pours in from windows, illuminating a charming work desk and decorative artwork on the wall.
Home in Greenwood Lake
4.99 out of 5 average rating, 185 reviews

Spectacular Lake Views from Every Room & Garden

Top guest favorite
A charming lakeside home with a red metal roof sits on a wooden deck overlooking the water. Surrounding landscaping features a serene pond, rocks, and green shrubs, creating a peaceful atmosphere. The setting sun casts a warm glow on the tranquil scene.
Home in Greenwood Lake
4.99 out of 5 average rating, 162 reviews

Amazing Lakefront Haven! Beach, Views, Free Kayaks

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

Guest favorite
An inviting open living space features large glass sliding doors that provide a view of the water. Natural wood accents complement the light-colored furniture, including a spacious sofa and a comfortable armchair, while a wooden coffee table sits centered on a soft area rug.
Home in Centerport
4.94 out of 5 average rating, 153 reviews

The Harbor House: Beachfront Home 1 hour from NYC

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

Top 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, 106 reviews

Captain’s Cottage Water Views -3 Bdrm

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, 142 reviews

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

Guest favorite
A dining area is presented featuring a dark wooden table surrounded by four white chairs. A decorative potted plant is centered on the table, complementing the modern decor. A doorway leads to a softly lit bedroom in the background.
Home in Port Jefferson
4.92 out of 5 average rating, 125 reviews

Port Jefferson Convenient, Cozy and Chic!

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Vacation rentals with pools in Long Island

Guest favorite
An indoor resistance pool is surrounded by a wooden deck, featuring calming turquoise water. Natural light floods in through large windows, while decorative sculptures and plants adorn the space, adding to the serene environment.
Guest suite in Redding
4.92 out of 5 average rating, 173 reviews

Artist Retreat in Beautiful Country Setting

Guest favorite
A spacious pool area is surrounded by a fenced perimeter, featuring a clear blue pool with lounge chairs. A covered pavilion and a playground are visible in the background, complemented by lush greenery and mature trees.
Guest suite in Northport
4.94 out of 5 average rating, 115 reviews

Coastal Villa Suite pool•sauna•gym•theater•beach

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, 126 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
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
4.95 out of 5 average rating, 182 reviews

Luxury cottage by the sea with hot tub and pool

Top guest favorite
Cottage in Southampton
4.96 out of 5 average rating, 189 reviews

Secluded Southampton Cottage w/Pool & Spa

Guest favorite
The image showcases a multi-story condo building set amidst neatly trimmed hedges. Sun loungers and patio umbrellas are positioned around a seasonal pool, which can be seen in the foreground. The design features white balconies and large windows, contributing to a light and airy appearance.
Condo in Greenport
4.92 out of 5 average rating, 142 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

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

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Home rentals with pools in Long Island

Top guest favorite
A serene backyard showcases a heated saltwater pool bordered by vibrant wildflowers. Tall trees provide shade, while a cozy seating area, visible in the background, complements the tranquil setting. Sunlight illuminates the landscape, highlighting the lush greenery and colorful blooms.
Home in Cutchogue
5 out of 5 average rating, 38 reviews

North Fork paradise between beaches and vineyards

Guest favorite
A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.
Home in East Hampton
4.88 out of 5 average rating, 112 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

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

Superhost
A modern home is set in a lush green environment, showcasing a spacious heated saltwater pool surrounded by a stone patio. Relaxing lounge chairs are placed alongside the pool, and the house features large windows that reflect the tranquility of the yard.
Home in East Hampton
4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

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, 46 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Guest favorite
A spacious heated in-ground pool is surrounded by a stone patio and vibrant landscaping. Lounge chairs are arranged along the poolside, accompanied by a large umbrella for shade. Lush greenery and blooming flowers frame the area, creating a serene outdoor retreat.
Home in Hampton Bays
4.97 out of 5 average rating, 60 reviews

4 BR Hamptons Oasis w/ Pool,Jacuzzi & Beach Access

Guest favorite
A landscaped yard features a swimming pool surrounded by red lounge chairs and a shaded seating area. Lush greenery provides privacy, while colorful plants offer visual interest. The adjacent house is visible, providing a spacious setting for outdoor activities.
Home in Dix Hills
4.96 out of 5 average rating, 27 reviews

Nice getaway with your family.

Guest favorite
Home in Greenwich
4.96 out of 5 average rating, 45 reviews

Riverfront Cottage Retreat & Pool 35 mins from NYC

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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.

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