Vacation rentals with a pool in Monroe

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Monroe

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

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Guest favorite

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4.89 out of 5 average rating, 187 reviews

4Br Mountain Brook House on 130 acres w/ trails

Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

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

4.96 out of 5 average rating, 134 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

A cozy sleeping area features a queen-size bed dressed in a red and black plaid comforter. Two lamps are positioned on either side, providing soft lighting. A small nightstand holds decorative items, while a trunk for storage is located at the foot of the bed.

Loft in Cornwall

4.85 out of 5 average rating, 633 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.

Top guest favorite

Home in New Paltz

4.98 out of 5 average rating, 524 reviews

midcentury mod * HOT TUB * walk out trail 2 mohonk

A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. IN GROUND SWIMMING POOL short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk a scenic mile to R2R trail (take to mohonk) Water St. mkt & the ❤️ of New Paltz Village THE WHOLE PLACE IS YOURS HOUSE & PROPERTY POOL (open 5/1-9/30) and HOT TUB (open 9/30-5/1)

Superhost

A spacious lounge area features a large corner couch with a mix of textures and colors. A round wooden coffee table sits centrally, surrounded by a cozy pouf and an armchair. Large windows provide natural light and views of the surrounding greenery.

Cabin in Vernon Township

4.78 out of 5 average rating, 286 reviews

Luxe 10 guest Ski Cabin Pools/Golf/Tennis/Gym/Hike

Gather your crew of 10 and escape to this stunning two-floor cabin, where adventure meets relaxation. Nestled in breathtaking scenery, this stylish retreat offers the perfect balance of comfort and outdoors. Whether you're hiking scenic trails, or simply unwinding, there's something for everyone. Enjoy year-round activities like skiing, snowboarding, mountain biking, wildlife spotting, or exploring the Appalachian Trail. This is more than a getaway it’s an experience you'll never forget!

Top guest favorite

A small red cabin is framed by lush greenery, with a welcoming porch featuring two wooden rocking chairs. Natural stone path leads to the entrance, surrounded by a forest of tall trees and soft moss-covered ground.

Cabin in New Paltz

4.95 out of 5 average rating, 157 reviews

The Little Shelter at Gunks EcoLodge

Now open in Winter, but subject to refunded cancellation if Snow makes the driveway unpassable for those without 4 or all wheel drive. This rental is a small cabin in the woods of New Paltz, NY. The cabin sleeps 4 with 2 twin beds in the loft and has a pullout couch with a quality queen size mattress. The kitchen is equipped but does not have an oven. Streaming TV and Internet. Check out our other listings at the EcoLodge, with Private Rooms/Baths, on the "About Me" page.

Guest favorite

A spacious main room is featured with high ceilings and a skylight. The kitchenette is visible alongside a dining table and chairs. A wooden coffee table sits in the living space, adorned with decorative items. Natural light flows through large windows framed by greenery.

Apartment in Chester

4.98 out of 5 average rating, 146 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 serene bedroom space features a spacious bed adorned with cozy linens and decorative throw pillows. Geometric wall carvings in dark tones create an artistic backdrop, complemented by bedside lamps providing soft lighting. Natural light fills the room through a nearby window.

Condo in Vernon Township

4.93 out of 5 average rating, 181 reviews

Resort Getaway @ Mtn. Creek -pool/hot tub/sauna

Ski-In-Ski-Out ! Top floor 1 bedroom Condo with Mountain/Pool View at Mountain Creek Resort. Steps away from ski mountain & gondola ! Swim in the outdoor heated saltwater pool, relax in the sauna or soak in the hot tub while taking in mountain views, Catch the sunset from your private top floor balcony or cozy up by your gas fireplace. Visit award-winning spas, golf, breweries, wineries, farms, and fine dining at Crystal Springs & Warwick, NY--only 10 min away.

Superhost

A charming blue house is nestled among lush green trees. A hammock is strung between two trees, while Adirondack chairs are arranged on a stone patio nearby. A small table and a grill are positioned in front of the house, complementing the serene outdoor setting.

Cottage in Rhinebeck

4.87 out of 5 average rating, 216 reviews

Secluded peaceful loft in barn by woods

La Barn Bleue sits on top of a hill by a forest, in a secluded and peaceful property. The main house, where we live is 150 feet down the hill. The apartment sleeps up to 4 people. The bedroom/lounge loft has one king bed and 2 twin beds. Ideal for families and kids above 5 years old. Because we use a rope railing, we cannot host kids under 5 years old for security reasons. We offer Wifi, AC/heat split unit, outdoor Picnic table, bbq, petanque court and pool!

Guest favorite

Home in Beacon

4.91 out of 5 average rating, 164 reviews

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

Welcome to Hudson Valley Hideaway — a stylish, family-friendly 4BR/2BA home tucked in the corner of Beacon just 1.5 miles from downtown & the Hudson River. Enjoy a chic living room w/ 85” TV, stocked kitchen, dining room, 1Gb WiFi, workspace & A/C. Sleep soundly in 1 King, 2 Queens & 1 Twin XL. Outside, unwind in the fenced oasis w/ pool, slide, hot tub, grill & fire pit. Modern comfort meets cozy Hudson Valley charm. SPECIAL: 20% OFF all winter stays!

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, 128 reviews

Private Retreat w/Pool, Hot Tub & Fire Pit, 6 BR

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 P26-0068

Top guest favorite

The interior features large windows allowing natural light to illuminate the space. A spiral staircase leads to the loft. A cozy seating area includes a white sofa and a decorative fireplace. Lake views are visible through the glass doors, enhancing the serene atmosphere.

Guesthouse in Brewster

4.99 out of 5 average rating, 325 reviews

The Cottage by the Lake: Hudson Valley Indulgence

The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.