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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Home in Suffern

5 out of 5 average rating, 3 reviews

HtdPool*PvtGym*HotTub*TheaterRm*Swingset*InNature!

NEW LISTING! This 5,100 home is the perfect spot for families looking to enjoy some wholesome fun. Situated on 1.5 acres and nestled between trees and nature, a stay at Suffern Estate is all you need to reset your mind. Rustic charm with a modern feel, this home was built to accomodate generations. Featuring a heated pool, hot tub, movie theater, home gym, swingset, and fully stocked with everything you need to move in for the week. Close to major arteries, yet tucked away for maximum privacy.

LocationFamilyAccuracy

A sunlit living room features a large sectional sofa adorned with decorative pillows. A coffee table sits at the center, complemented by a flower arrangement. The windows are lined with festive greenery and accents, enhancing the space's warmth and charm.

Home in River Vale

4.94 out of 5 average rating, 47 reviews

Cozy Family Chateau Close to NYC avail Longterm

Impeccably Clean & Private, 35 min drive into NYC, Unique living space on 4 levels. Private entrance to office, surround sound, 2 Fireplaces, 3 bedroom, 3 bathroom. Beautiful kitchen to cook and socialize around. The sunroom is furnished for reading a book under the sun and among the greenery. Main dining table seats 8. Heated pool with sun deck and hot tub. Outdoor barbecue & new patio. Additional patio off bedroom. Great hiking and trails nearby. This property is the perfect family getaway.

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Top Guest favourite

Home in Croton-on-Hudson

5 out of 5 average rating, 47 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).

LocationFamilyBathroom

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

4.9 out of 5 average rating, 94 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

Home in Suffern

4.91 out of 5 average rating, 53 reviews

Group Retreat | Pool, Hot Tub & Gourmet Kitchen

*POOL IS OPEN* Enjoy warm weather at this peaceful mountain retreat just an hour from NYC. Lounge on the patio with a BBQ, fire pit, hot tub, or spacious backyard with stunning views, or cool off in the pool. Inside, bright living spaces filled with natural light, a full gourmet kitchen, and cozy bedrooms with sparkling clean bathrooms make it perfect for families or groups. Explore nearby trails, relax outdoors, or unwind with games and movies indoors. Great for the whole group!

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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

4.86 out of 5 average rating, 29 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!

ValueFamilyView

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 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.

LocationFamilyTV

Home in Croton-on-Hudson

4.7 out of 5 average rating, 40 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 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.

LocationFamilyComfort