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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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Top guest favorite

The exterior of a Mid Century Mod house is showcased at night, illuminated by soft outdoor lights. The building features large windows that reveal glimpses of the interior, while the surrounding lawn is landscaped with grass and scattered fallen leaves.

Home in New Paltz

4.98 out of 5 average rating, 508 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. fireplace, 5 person hot tub 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)

An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.

Home in Newburgh

4.82 out of 5 average rating, 108 reviews

Entire Home (private pool), Event Friendly

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

Top guest favorite

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

4.96 out of 5 average rating, 370 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

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.

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.

Top guest favorite

A cozy living space is highlighted by a light wooden floor and a white shiplap ceiling. A comfortable brown leather couch and an orange accent chair provide seating. A wooden coffee table sits in front of the sofa. Wall art and a floor lamp add warmth to the room.

Cottage in Kingston

4.93 out of 5 average rating, 392 reviews

Kapitan’s Cottage Private Upstate Catskill Retreat

A vintage rustic country retreat with two floors with modern amenities. 2BR, full & half bathroom. Family & Pet friendly. Large yard surrounded by a mature tree line for secluded privacy. Private stone deck w/ fire pit, BBQ & comfortable deck furniture. Summer Pool access and Generator on site. Close to Kingston, High Falls, Stone Ridge and Woodstock yet just far enough out to feel you're away from city hustle and bustle. Close to miles of hiking, outdoor activities, parks & Ski slopes.

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 Mountainville

4.84 out of 5 average rating, 589 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.

A well-appointed studio room features a spacious king bed with plush bedding and decorative pillows. A stylish desk with a chair is positioned alongside a modern seating area, complemented by a coffee table. Natural light floods the space through large windows, enhancing the warm atmosphere.

Condo in Vernon Township

4.92 out of 5 average rating, 271 reviews

Upscale Condo Ski-In/Out Mountain Creek 1 hr NYC

Voted NJ’s #1 new host!!! Experience a grand escape in our NEW UPSCALE and LUXURIOUS STUDIO at The Appalachian Hotel at Mountain Creek, NJ. The most convenient ski-in ski-out resort, just walk to the lifts. BOOK NOW and go skiing, snowboarding, snow tubing, hot tub & heated pool swimming, mtn biking, horseback riding, hiking, golf, water park, visit farms, wineries & more! Then, relax at our super soft king bed, sleeper sofa, amazing bathroom and cozy fireplace. You'll love it!

A spacious living area is centered around a stone fireplace, adorned with wood beams. Natural light filters through large glass doors, offering views of the greenery outside. Comfortable couches are positioned invitingly, creating a relaxing atmosphere for guests.

Home in Cold Spring

4.95 out of 5 average rating, 174 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.

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

4.94 out of 5 average rating, 164 reviews

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

NEWLY Renovated! 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.

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

4.99 out of 5 average rating, 137 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.

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.

An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.

Cottage in Putnam Valley

4.94 out of 5 average rating, 100 reviews

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Escape to a stylish 3BR cottage with a private pool, cinema room, game room, and fire pit - perfect for families, couples, or solo travelers. Surrounded by woods and just minutes from Cold Spring, hiking trails, ski resorts, and charming shops. Relax by the electric fireplace, enjoy movie nights, play pool, or unwind with forest views from your private deck. A cozy, well-equipped retreat for peaceful getaways and Hudson Valley adventures year-round.

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Popular amenities for Monroe rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 72 reviews

The Hudson Hideaway~Pool, Hot Tub, Sauna~1hr toNYC

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

4.88 out of 5 average rating, 163 reviews

4Br Mountain Brook House on 130 acres w/ trails

Top guest favorite

An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.

Home in Saugerties

5 out of 5 average rating, 156 reviews

Upstate Modern Scandinavian Barn in the Catskills

Home in Narrowsburg

4.94 out of 5 average rating, 219 reviews

Modern House with Hot-Tub and Fireplace

A spacious backyard is highlighted by a shimmering in-ground pool surrounded by lounge chairs and cabana umbrellas. Lush greenery frames the area, creating a tranquil atmosphere. A slide is visible in the pool, and a vibrant blue sky with clouds adds to the inviting scene.

4.91 out of 5 average rating, 149 reviews

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

Home in Grahamsville

4.9 out of 5 average rating, 107 reviews

Spacious Catskills Farmhouse on over 5 acres!

Top guest favorite

A two-story home with a light-colored exterior and burgundy shutters is set against a clear blue sky. The well-maintained lawn features manicured shrubs and trees, enhancing the inviting curb appeal. The entrance is framed by steps leading to the front door, creating an approachable feel.

Home in Chester

5 out of 5 average rating, 22 reviews

4 Bedroom Home with Hot-Tub

A serene landscape capturing a peaceful lake surrounded by dense greenery. The calm water reflects the trees and sky, creating a tranquil scene. Soft ripples disturb the surface, while patches of grass and fallen branches line the water's edge.

Home in Woodridge

4.85 out of 5 average rating, 101 reviews

Pool Hot tub Sauna Canoe Country Lakehouse

Condo rentals with a pool

A cluster of rustic-style buildings is nestled among trees, showcasing a warm wooden facade. Each unit features a balcony with sliding doors, while stairs lead to the entrance. The scene is enhanced by the surrounding greenery and the hints of fall colors in the leaves.

Condo in East Stroudsburg

5 out of 5 average rating, 5 reviews

Wyndham Shawnee Village | 2BR/2BA Balc Queen Suite

An illuminated salt-water pool reflects soft light at night, surrounded by a well-maintained patio. The backdrop features a multi-story building with balconies and warm lights glowing from the windows, creating a serene atmosphere.

Condo in Vernon Township

4.89 out of 5 average rating, 132 reviews

Valley Overlook @ Mtn Creek Resort Park & Play

Top guest favorite

A cozy living area features a comfortable sofa accompanying a rustic coffee table. A large window showcases mountain views, while natural light enhances the space. A wall-mounted television is placed above a gas fireplace, with minimalist decor elements positioned for a welcoming atmosphere.

Condo in Vernon Township

4.97 out of 5 average rating, 104 reviews

Cozy Retreat | Pool & Hot Tub | Mountain Creek Resort @ Appalachian

A series of wooden structures are positioned on a hillside, surrounded by trees. An expansive green field lies in the foreground, with a golf cart visible near the edge of the grass. The sky is clear with a few scattered clouds.

Condo in East Stroudsburg

4.75 out of 5 average rating, 4 reviews

Shawnee village, Poconos timeshare

The exterior of the Appalachian building is shown, featuring a combination of vibrant wood siding in warm hues and decorative green shutters. Balconies are visible, nestled among well-maintained landscaping, creating a welcoming entrance leading to the facility.

Condo in Vernon Township

4.95 out of 5 average rating, 203 reviews

Comfy Studio at Mountain Creek Resort

A spacious living area features a comfortable sofa, a bright yellow chair, and a dark wooden coffee table. A gas fireplace is situated beneath a wall-mounted TV, with natural light filtering through large windows. A small desk and plant add functional and decorative touches.

Condo in Vernon Township

4.97 out of 5 average rating, 58 reviews

Deluxe 1 Bdr | Walkout Patio to Pool & Hot Tub! | Mountain Creek Resort @ Appalachian

Top guest favorite

The living room features a cozy sectional sofa and a wooden coffee table positioned in front of a modern electric fireplace. A flat-screen TV is mounted on a textured wall, displaying various streaming options. A dining area with a table and chairs is visible, creating a welcoming space.

Condo in Vernon Township

4.94 out of 5 average rating, 81 reviews

Comfortable, chic, modern and sophisticated condo

A panoramic view showcases lush green mountains surrounding a winding river below. The landscape features a mix of rolling hills and dense foliage under a bright blue sky, with scattered clouds adding depth to the serene scene.

Condo in East Stroudsburg

4.88 out of 5 average rating, 8 reviews

Shawnee Village, PA, 2 Bedroom King Depuy #1

Other vacation rentals with a pool

Top guest favorite

A two-story house features a classic blue exterior with white trim. A covered porch is visible at the front, offering a welcoming entrance. Lush greenery surrounds the home, and trees provide a natural backdrop, enhancing the serene country setting.

4.99 out of 5 average rating, 89 reviews

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor

Top guest favorite

A spacious backyard is featured, showcasing a well-maintained lawn, a wooden deck surrounding a private pool, and a fire pit area. The house's exterior is light grey, complemented by tall trees offering shade. A gazebo is visible, providing an ideal setting for outdoor gatherings.

Home in Warwick

4.99 out of 5 average rating, 71 reviews

4 bedroom house with pool (Kids & Dog Friendly)

Top guest favorite

A modern home is seen from the patio, showcasing large glass windows and balconies on the second floor. The space is surrounded by greenery and features a pool in the foreground with a stone patio. Lounge chairs and umbrellas are arranged nearby for relaxation.

Home in Wappingers Falls

5 out of 5 average rating, 73 reviews

Luxe Wooded Modern Getaway Retreat + Spa

A spacious kitchen features modern appliances, including a stainless-steel refrigerator and oven. An island with seating for four is illuminated by natural light from large windows. Open shelving displays various kitchenware against a clean, white backdrop.

Cabin in Warwick

4.83 out of 5 average rating, 40 reviews

Luxury Woodland Cabin Getaway near Warwick

Cabin in Forestburgh

4.98 out of 5 average rating, 54 reviews

Spirit Cabin: Lakefront w/Pool-Sauna-Cold Plunge

Top guest favorite

The living area features a comfortable couch and armchair, with large windows providing natural light and views of the outdoors. A wooden dining table with four chairs is positioned near the windows, while a coffee table sits in front of the couch. Shelves hold various books and decorative items.

Guest suite in New Paltz

4.95 out of 5 average rating, 404 reviews

Airy & Private Escape on Mountain Rest Road *Pool*

Top guest favorite

The cottage is tucked amidst vibrant autumn foliage, framed by trees. A large front deck, furnished with two chairs, provides a serene entry, while the three expansive windows invite natural light. The wooden exterior blends harmoniously with the surrounding woodland.

Guesthouse in Bedford Hills

5 out of 5 average rating, 66 reviews

The Perch, a luxe cottage in the woods 1h from NYC

The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.

Guesthouse in Pound Ridge

4.94 out of 5 average rating, 98 reviews

A Lovely Cottage in the Woods

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