Vacation 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 favorite

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

4.95 out of 5 average rating, 132 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.

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.

Home in Monroe

5 out of 5 average rating, 3 reviews

The Sweet Spot: Fab Fall Getaway 1hr from the GWB!

Just 1 hour north of NYC, enjoy a wonder-filled vacation at your sweet retreat. So much to do and see in NY's famed Hudson Valley, or just do nothing at all but relax in your own one-of-a-kind, designer oasis. The Sweet Spot offers tons of entertaining space, indoors and out, modern high-end finishes, five bedrooms, and an open concept chef's kitchen. There's a heated, salt-water pool and party barn in summer, gorgeous fall leaves, local skiing, hiking, shopping, golfing, and so much more.

The spacious living area features warm wood-paneled ceilings and skylights, providing ample natural light. Leather couches surround a glass coffee table, and a fireplace adds a cozy touch. A stylish wet bar is visible in the background, with large windows overlooking the outdoor scenery.

Home in Monroe

4.9 out of 5 average rating, 69 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.

Guest favorite

The living room features two light-colored sofas and two dark green chairs arranged around a coffee table. A fireplace is centered on the wall, with large windows providing natural light. A green feature wall and vaulted ceiling enhance the spacious feel of the room.

Home in Suffern

4.93 out of 5 average rating, 29 reviews

Cozy Fall Home with 4BR and Fireplace Close to NYC

A tranquil oasis just an hour from NYC, this spacious, elegant Airbnb is set on a private, wooded lot with a huge backyard. Take a dip in the sparkling pool, fire up the grill, and dine al fresco on the patio, then gather around the fire pit surrounded by nature for the perfect escape from the day-to-day. Inside, you’ll find upscale furnishings, an enormous kitchen, plenty of places to relax, large flatscreen TVs, a game room with a pool table and, a kids’ reading area, & more.

Top guest favorite

Tent in Monroe

5 out of 5 average rating, 6 reviews

Large Tent - You setup air mattresses

Large family tent with 2 queen size air mattresses that you setup. Pillow, and flat sheets all inside the pool house. You prepare and enjoy! Fridge, bathroom. Electricity and WiFi all included! Fire pit & hot tub, basketball court! 3 hoops! Plenty seating, tables and chairs! Shower with full private bathroom. The pool house is shared with host family! Kid friendly! Lots of board games and toys! , Sandbox & trampoline! FYI..There is no pool. Above ground pool taken down.

A cozy bedroom features a light-colored quilted bedspread placed atop a spacious bed. A bedside lamp is positioned next to the bed, while a large potted plant stands on a slender table near a window, which is adorned with green curtains.

Home in Valley Cottage

4.9 out of 5 average rating, 10 reviews

Relaxing Family Retreat

Come relax with your family in this peaceful home. It’s a beautiful split family ranch with the top floor completely private to guests. En suite master bedroom boasts both a soaking tub and a standing shower. Located a 5-minute drive from the Palisades Center, a 5-minute drive from Rockland Lake State Park, and a 10-minute drive from the bustling downtown Nyack, you will find something for everyone in the family to enjoy. Or enjoy the deck, barbecue, and pool at home.

Guest favorite

A modern kitchenette is displayed, featuring white cabinetry and stainless-steel appliances. A comfortable brown sofa is positioned near a wooden coffee table. A dining area with a white table and chairs is also visible, alongside large windows allowing natural light into the space.

Apartment in Suffern

4.94 out of 5 average rating, 147 reviews

Renovated Forest Oasis with Pool & Fire-pit

Get away from it all in this nature lovers retreat! Serenity abounds in this fully renovated 1 bedroom apartment with private entrance. Located on a 5 acre property abutting Harriman State Park with direct access to hiking trails. Guests are welcome to use the pool and hot tub (Memorial day through Labor day), or sit and enjoy a fire pit by the babbling brook. Fenced dog run for your furry friend. Just 30 minutes from the GWB and minutes from the train and bus.

Guest favorite

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

5 out of 5 average rating, 11 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!

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

4.87 out of 5 average rating, 71 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!

Top guest favorite

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.

Camper/RV in Suffern

5 out of 5 average rating, 51 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.

Home in Croton-on-Hudson

5 out of 5 average rating, 3 reviews

Private Suite in the Heart of the Hudson Valley

Private suite in Croton-on-Hudson with its own entrance, full bath, and a striking 6-ft circular window overlooking the trees. Enjoy access to an outdoor fire pit, on-site parking, and easy transit via nearby Metro-North stations. Pet friendly and close to the Hudson River, great restaurants, hiking trails, and scenic overlooks—an ideal base to explore the beauty of the Hudson Valley by day and return to a cozy retreat at night.