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

Guest suite in Croton-on-Hudson

4.98 out of 5 average rating, 125 reviews

Enchanting Farmhouse Suite w/ pool and sauna

Set in historic 1750's farmhouse, located in the center of Teatown Lake Reservation with over 1,000 acres of trails in our backyard, this elegant getaway has all the luxuries of a resort (pool, cedar barrel sauna, spa tub, rain shower) while maintaining the rustic charm of a working farm. Easily accessible to NYC, yet worlds away-- a chic private refuge where you can unwind and restore to the gentle sounds of nature (& the occasional rooster.) Friendly dogs and artists:) Sorry, no kids or pets.

Guest favorite

Home in Beacon

4.92 out of 5 average rating, 111 reviews

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Welcome to Hudson Valley Hideaway, a stylish family friendly home tucked away in the corner of Beacon, off the shores of the Hudson. 4 Bedrooms, 2 bath, pool+hot tub home, stocked kitchen, dining room, chic living room w/ 85"TV, 1 King, 2 Queens, 1 Twin XL, with fast internet (1gb), dedicated workspace & A/C. Amenities galore, outdoor space w/grill, firepit and fenced pool w/ slide & diving board. Experience a little slice of Beacon in this cozy home with modern city comforts,1.5 miles from DT

Guest favorite

Home in West Milford

4.98 out of 5 average rating, 132 reviews

On The Rocks In The Hot Tub

Unique home featuring a large deck with an enclosed hot tub, indoor/outdoor bars, game room and seasonal pool (pool is not heated) Fall-Winter:Minutes away from the town of Warwick. Pennings, Heaven Hill Farm for apple-pumpkin picking, Peter Mountain, Mountain Creek for skiing. Many vineyards/cideries Summer: Boating on Greenwood Lake, kayak rentals, hiking (Appalachian Trail), drive-in theater, family activities at Wawanique State Park, Crystal Springs Golf and ice cream at Bellvale Creamery

Guest favorite

Home in Monroe

4.96 out of 5 average rating, 111 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.

Guest favorite

Home in Yorktown Heights

4.9 out of 5 average rating, 135 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

Home in Newburgh

4.98 out of 5 average rating, 100 reviews

Beautiful riverfront mid-century house

Friends and family will be wowed when gathering at this spacious and ultra comfortable home. There’s a beautiful new gunite pool, hot tub, large patio, screened in porch, and spacious deck for barbecuing and dining. Interiors feature 2 fireplaces, 2 living spaces with large TVs, fully-equipped kitchen, game room, exercise area, piano, home office, and lots of space to spread out both inside and outside. All of it looks out to the Hudson River where you may spy bald eagles nesting nearby.

Guest favorite

Home in Cornwall-on-Hudson

4.89 out of 5 average rating, 115 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, 2 TVs, 1-new Smart, one with ROKU, 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.

Guest favorite

Barn in Katonah

4.97 out of 5 average rating, 117 reviews

The Magic Red Barn

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

Home in Cold Spring

4.94 out of 5 average rating, 163 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

Rental unit in Suffern

4.94 out of 5 average rating, 127 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

Loft in Cornwall

4.86 out of 5 average rating, 461 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 flat screen Roku TV with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have their own parking space, a private first-floor entrance, full bathroom, patio, BBQ and fire pit!

Guest favorite

Rental unit in Fairview

4.93 out of 5 average rating, 119 reviews

Cozy+Modern 1BD/1BA Apt-Near NYC

Welcome to StayandSleep collection. This beautiful, clean and modern 1 bedroom apartment with NYC views has everything you need to relax in style. Seconds away from NYC transportation via bus. Great location for your stay, where you are greeted with nearby activities such as restaurants, shopping centers, American Dream Mall, Met Life Stadium, Soho Spa club ect. Our neighborhood is friendly, safe and secure.