
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.

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

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.

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.

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)

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!

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.

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.

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.

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!

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!

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

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.
Popular amenities for Monroe rentals with a pool
House rentals with a pool

Scenic River View Escape | New Paltz

Highwoods Haven | saltwater pool and hot tub

Golf Sim! Hot Tub/Game Room/Cinema 2 Kings

Cozy & Spacious Country Home - All Seasons

6-Acre Lux Estate: Hot Tub, Fireplace, Near Skiing

Peace & Privacy - High Falls (hot tub & salt pool)
Fenced & Salt Water Pool | Cozy Catskills Cottage

Luxury Retreat with pool in historic Kingston
Condo rentals with a pool

Premium New 1bd Sunset balcony 3rd flr

Valley Overlook @ Mtn Creek Resort Park & Play

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

Cozy condo in Ski Resort. 2 bedroom/2 bath Unit226

Comfy Studio at Mountain Creek Resort

Modern Lodge Condo | Mountain Creek Escape

Modern Ski in/out/waterpark/King Bed/WIFI/Parking

Condo at Mtn Crk 1 Bdr 1 Bath sleep 4 Mtn view 308
Other vacation rentals with a pool

4 bedroom house with pool (Kids & Dog Friendly)

Stunning Mountain Cabin w/ Pool & Hot Tub

The Barger Wixon House

Arkadia House Mid-century retreat with pool & view

Serene Hudson Valley Escape Hottub/Pool/King Suite

New Paltz dog friendly retreat w/salt water POOL

Luxury Villa w Lake View | Hottub | Summer Pool

Private Family villa with pool hot tub
Destinations to explore
- Plainview Vacation rentals
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- Times Square
- Madison Square Garden
- New York City Center
- Brooklyn Bridge
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Bronx Zoo
- Mountain Creek Resort
- Rockefeller Center
- Grand Central Terminal
- Yankee Stadium
- United Nations Headquarters
- Bryant Park
- Empire State Building
- Citi Field
- Bethel Woods Center for the Arts
- Statue of Liberty
- Radio City Music Hall
- Old Glory Park
- Bushkill Falls
- USTA Billie Jean King National Tennis Center
- Thunder Ridge Ski Area
- The Metropolitan Museum of Art




