Holiday rentals with a pool in Rockland County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Rockland County

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

A scenic view from the steps leading down to the backyard, showcasing a heated pool surrounded by a fenced patio and a newly installed hot tub. Lush green lawn and vibrant flowers complement the serene lake visible in the background, providing a tranquil outdoor atmosphere.

Home in Monroe

4.96 out of 5 average rating, 141 reviews

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

Kitchen & Basement Newly Finished!! Enjoy your very own LAKEFRONT WONDERLAND with a trove of amenities and space to WFH with fast internet! A perfectly manicured landscape with a Goldilocks-sized pool. The lawn leads to your very own private dock and brick patio, containing a fire-pit. Swim to your heart's content in the pool or in the lake. Soak in the hot tub. Paddle in our canoe or kayak and try snagging some brown trout. Plenty of room for a large extended family or a group of friends.

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Top Guest favourite

Home in Croton-on-Hudson

5.0 out of 5 average rating, 48 reviews

Beautiful 5-Acre Oasis + Pool in the Hudson Valley

Welcome to our guest house! We invite you to enjoy our lush, peaceful, 5-acres of land in beautiful Croton-on-Hudson. Drive up the long, picturesque driveway to reveal our two houses (yours and mine) which are fairly far apart, providing you with plenty of privacy in your standalone house. We love when guests explore our entire property and make themselves at home by using our outdoor hammocks, tree swings, pool, fire pit, many chairs, and even a zip line for kids (all shared only with us).

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Superhost

Home in Chester

New place to stay

Woodland Retreat in KJ, Monroe & Chester!

Discover your perfect vacation, or home from work at this serene home retreat centrally located near KJ/Monroe/Chester, NY! 1 hour drive from NYC, you’ll soak in a woodland atmosphere unlike any other. Our unique space is set in the lower floor of a charming, rustic cabin, surrounded by lush greenery and towering trees. Kindly, read the entire listing description to ensure our home meets your needs and expectations, as this is crucial for a 5-star experience, especially regarding location.

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Apartment in Spring Valley

5.0 out of 5 average rating, 3 reviews

Newly Renovated APT|Close to Hospitals|30 mins NYC

Completely & thoughtfully renovated featuring modern furnishings, king size bedroom, work space & huge walk-in closet. Included in your stay, you'll have full access to brand new fully-equipped kitchen with all major appliances (refrigerator, stove top w/oven) and bathroom, high-speed wifi, complimentary coffee, heating, air conditioning in warmer months, laundry room on site, assigned parking space, linens, towels, & cleaning supplies. Accommodates up to 1 guest or a couple comfortably.

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Guest favourite

A serene outdoor space showcases a heated pool surrounded by a lush green lawn and vibrant trees. A wooden deck extends nearby, featuring comfortable seating and a tranquil setting for relaxation and gatherings.

Home in Monroe

4.91 out of 5 average rating, 97 reviews

Spacious Home w/Pool/Hot Tub, Mins to Parks/Skiing

This stunning 3-bedroom, 4-bathroom home, tucked away in the woods of Monroe, is just minutes from scenic NY state parks, ski resorts, and wineries. Combining modern amenities with rustic cabin vibes, this spacious retreat offers the perfect blend of comfort and style. Nature enthusiasts can explore the private backyard with a lush garden and heated pool. With elegant living spaces, a game room, and an outdoor wraparound deck, guests will enjoy the ultimate mix of relaxation and luxury.

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Guest favourite

A spacious outdoor area features a large swimming pool surrounded by a paved patio. The villa, with a red-tiled roof, stands in the background amidst lush greenery. Sun loungers are arranged at the pool's edge, inviting relaxation.

Villa in Monroe

4.94 out of 5 average rating, 70 reviews

Mediterranean villa •pool•hot tub•fire place

Discover the Mediterranean Villa, a stunning 5-bedroom, 4-bath luxury retreat nestled in the scenic Hudson Valley. This Monroe, NY escape offers elegant interiors, a cozy wood-burning fireplace, outdoor fire pit ,Smart TVs, a private hot tub, spacious living areas designed for comfort and style. Perfect for families or groups, it’s minutes from Catskills trails, Woodbury Commons shopping, and Legoland. Unwind, explore, and indulge in upscale relaxation year-round.

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Guest favourite

A spacious outdoor patio features several white Adirondack chairs arranged around a central fire pit. The quaint cottage, with a blue accent awning, is nestled among green trees, providing a serene backdrop. The area is well-lit by natural sunlight and includes a lawn in the distance.

Cottage in Monroe

4.87 out of 5 average rating, 30 reviews

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Cozy Fireside Gatherings | Deck w/ Wooded Views | 10 Mi to Legoland | Day Trip to NYC Stay and play in Monroe, known as the Lake Region of New York's Hudson Valley! This charming 2-bedroom, 1-bathroom vacation rental cottage offers a laptop-friendly workspace, a well-equipped kitchen, and quiet outdoor spaces. When you're ready to venture, hike to the picturesque Fitzgerald Falls, step back in time at Museum Village, or visit a local brewery or winery!

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Superhost

An aerial view captures a spacious backyard featuring a fenced-in heated pool and hot tub. Surrounding the area are lounge chairs on a sun deck, a shaded gazebo, and landscaped gardens, creating an inviting outdoor retreat. The home is visible in the background.

Home in Harriman

4.88 out of 5 average rating, 82 reviews

The Hudson Hideaway~Pool, Hot Tub, Sauna~1hr toNYC

Escape to your home away from home retreat featuring a heated pool, hot tub, and sauna. Enjoy the pool until October 14, 2024, before it reopens in May 2025. This smart Colonial home offers a spacious fenced in yard, deck with large grill, and a cozy fire pit lounge. Just 1 hour from NYC, and close to Woodbury Commons Outlet, Harriman State Park, local breweries, wineries, and restaurants. A perfect spot for everyone to unwind and explore!

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Top Guest favourite

The image displays a shaded outdoor area featuring an Airstream Cruiser beneath a wooden pavilion. Several lounge chairs and a colorful striped blanket offer comfortable seating. Surrounding greenery and a pebble border enhance the space, providing a serene atmosphere for relaxation.

Campervan/RV in Suffern

5.0 out of 5 average rating, 56 reviews

'54 Stream

Just 40 minutes north of NYC on the edge of Harriman State Park this unique, fully restored, 1954 Airstream is equipped with all the functionality of the modern world. Perched beside a stream and under a purposely built pavilion the Airstream dream comes alive with its own patio, BBQ, fire pit, and charming barn. From Memorial Day to Labor Day, enjoy shared access to our heated saltwater pool—perfect after a day of hiking. Towels provided.

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Home in Croton-on-Hudson

4.71 out of 5 average rating, 41 reviews

Private Suite in the Heart of the Hudson Valley

Enjoy a private Croton-on-Hudson suite featuring its own entrance, bathroom, and a striking 6-ft circular window overlooking the trees. This pet-friendly retreat offers a seasonal summer pool, outdoor fire pit, on-site parking, and easy Metro-North transit. Perfectly located near the Hudson River, restaurants, and hiking trails, it serves as the ideal base for daytime exploring and cozy nights. No parties please.

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Superhost

Home in Monroe

4.75 out of 5 average rating, 4 reviews

Peaceful & Spacious Home with Pool

Discover the epitome of serenity in this stunning home. Forget your worries in this spacious and serene space. This home is bright, airy, and generously sized. Multiple living rooms and an open-plan kitchen/dining are perfect for spending time with friends and family. Head out back to splash around in the pool, relax by the fire pit, or cook up a feast on the grill.

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Top Guest favourite

Home in Orangeburg

5.0 out of 5 average rating, 5 reviews

Matt’s Cozy Quarters Near NYC w/Outdoor Living

Peaceful and beautifully renovated 3BR/2BA home in NY with seasonal pool access (June 15–Oct 1), outdoor living space, off-street parking, and quick access to NJ via the Palisades Parkway. Close to shops, dining, and local attractions while offering a quiet, relaxing retreat.

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