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 serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.

Home in Stormville

4.94 out of 5 average rating, 182 reviews

Private Hudson Valley Country Retreat

Beautiful 1930s house set on 18 private acres of land overlooking a private lake. Immaculately landscaped surrounding area with koi and gold fish pond with a waterfall, gazebo, hammock and most importantly untouched nature. Very private! Enjoy your morning coffee or tea in the outdoor covered patio overlooking the property, wine and dine under the pergola, enjoy the fire pit or wood burning fireplace on a chilly evening. Serenity and relaxation at its best! Pond dock coming up in Spring of 2021

Top 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

4.97 out of 5 average rating, 118 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.

Top guest favorite

The image shows a well-kept swimming pool surrounded by a fenced area and lush greenery. Brightly colored flowers in a hanging planter add a touch of color to the foreground. Poolside lounge chairs are arranged on a textured surface, inviting relaxation.

Apartment in Wappingers Falls

5 out of 5 average rating, 210 reviews

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

PLEASE READ ALL HOUSE RULES PRIOR TO INQUIRIES AND BOOKINGS! 1 night/longer stays can be accommodated upon request and calendar availability. “Home Is Where The Heart Is”. If you love tranquility and coziness combined with sophistication and traditional rural charm, this is the place for your stay (only 4 miles from Beacon). The ground floor apartment with a private entrance (located around the back in a private house) includes a living room, full kitchen, full bathroom and Queen bedroom.

Guest favorite

A circular pool is set on a wooden deck, shimmering under natural light. Lounge chairs are positioned nearby, providing a space to relax. Green trees and grass create a tranquil backdrop, contributing to the serene outdoor setting.

Loft in Cornwall

4.85 out of 5 average rating, 538 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

Guest favorite

A serene pool area surrounded by lush greenery is depicted. The clear water reflects the surrounding trees, creating a tranquil atmosphere. Stone pathways and decorative plants frame the pool, inviting relaxation in a peaceful outdoor setting.

Home in Yorktown Heights

4.91 out of 5 average rating, 154 reviews

Cozy getaway 1 hr from NYC!

This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms and a POOL. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook & seating area! Bedroom 1: King size bed & pack n play. Ensuite bathroom. Bedroom 2: Queen size bed, dresser. Ensuite bathroom. Bedroom 3: King size bed, pull out couch. Ensuite bathroom. Living room: Pull out couch. Pool is open Memorial Day - Labor Day. Heated by the sun- no heater.

Guest favorite

A heated saltwater pool is surrounded by a spacious, fenced lawn. The pool area features wooden decking and chairs for relaxation. Towering green trees provide a natural backdrop, emphasizing the tranquil outdoor setting near the private barn.

Barn in Katonah

4.97 out of 5 average rating, 124 reviews

The Magic Red Barn with heated pool now opened!

Experience country magic one hour from NYC! Our heated saltwater pool offers a perfect retreat. Enjoy nearby farmers' markets, Muscoot Farm, and scenic orchards. Stay in a renovated 1,000 sq ft luxury loft on the second floor of a private barn that includes: 1 king , 2 queen , and 1 toddler beds, a full kitchen (half-size fridge, mini freezer), microwave, and full-size oven. Ideal for guests who need to « escape ». Enjoy privacy—no other guests. Good Wi-Fi and full-house generator.

Guest favorite

A serene salt-water pool reflects the surrounding greenery and blue sky. The natural stone edge frames the pool, while two lounge chairs are positioned nearby, creating a peaceful outdoor retreat.

Home in Cold Spring

4.95 out of 5 average rating, 170 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Guest favorite

A two-story house is situated on a quiet residential street, featuring a white exterior with a contrasting brick foundation. The entrance is framed by multiple windows, allowing natural light to illuminate the interior. A well-maintained yard with greenery surrounds the property.

Home in Cornwall-on-Hudson

4.87 out of 5 average rating, 126 reviews

Eclectic, Sleeps 5, Wsher/Dryer, Parking, Yard, AC

This is a 2-story house-quiet residential street-safe town. Clean, eat-in kitchen, dining room, 2 twins, one queen, fold out bed in Living Room, shower/tub, washer/dryer, dedicated work area, Internet TV and ROKU 2nd floor, art supplies, large backyard, sml bbq, fire pit, games, kid-friendly. Free on/off-street parking. Close to Storm King, the Hudson, Woodbury Mall, West Point, hiking, restaurants, bars, malls. Town pool easy walking distance. No river or mountain view.

Top guest favorite

A private pool is situated at the back of the property, featuring a deep end and a diving board. The pool is surrounded by lush greenery and landscaped vegetation, creating a tranquil outdoor space. The area includes a paved deck for relaxation.

Apartment in Chester

4.98 out of 5 average rating, 106 reviews

Private Country Getaway

This family-friendly apartment is an hour from NYC, with a private driveway and entrance. The location is ideal for a getaway in any season. In the Warwick Valley, the property is 10 min from Legoland, and 13 min from the NY Renaissance Festival, surrounded by vineyards, orchards, farms, breweries, state parks, skiing, and the Appalachian Trail. 5 minutes from historic Sugar Loaf and the Sugar Loaf Performing Arts Center. 15 min from Woodbury Commons Premium Outlets.

Guest favorite

A spacious outdoor area features a rectangular pool bordered by vibrant greenery. A hot tub is situated adjacent to the pool, surrounded by potted plants. Comfortable seating is provided under a gazebo, contributing to a serene environment for relaxation.

Apartment in Suffern

4.94 out of 5 average rating, 131 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

An aerial view of a house is surrounded by dense green trees, with a clear pool visible in the backyard. The lawn is lush and includes a pathway leading to the pool area, blending harmoniously with the natural landscape.

Home in Warwick

4.92 out of 5 average rating, 109 reviews

Summer Retreat! Amazing Pool, Playground, 7 acres!

Enjoy an incredible house set on 7 acres with every amenity you can think of in an amazing town only 90 minutes from anywhere in NYC. Close to Skiing(15 minutes to Mountain Creek or Mount Peter) hiking, farms, wineries, breweries, amusement parks, a drive-in movie theater and SO much more! You choose to explore the local town or stay home and enjoy the heated pool, playground, or host dinner in our large dining room. Permit number 33341

Guest favorite

A serene outdoor pool is surrounded by well-maintained lawns and lounge chairs. The landscape features rolling green hills and a clear sky, inviting relaxation and leisure in a natural setting.

Farm stay in Warwick

4.88 out of 5 average rating, 135 reviews

Stunning Historic Large 1747 Estate

Just 50m from NYC on 140 acres this elegant Shaker farm house has impeccable historic credentials and original features. Perfect for winter getaways with two wood burning fireplaces and dramatic dining room for entertaining. Crisp country air on an afternoon hike. Snowshoeing, skiing and sledding. Please inquire about our Chef curating a memorable dinner using locally sourced ingredients.