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

Condo in Vernon Township

4.98 out of 5 average rating, 303 reviews

Hike, Bike, Wine | Rustic Chic Stays

Ski-In/Ski-Out, Waterpark & Biking fun- Just Steps Away! Ski/snowboard, bike, hike, zip line - or relax in the Appalachian's year-round heated outdoor pool, hot tubs, & sauna. This 1-bedroom, 1-bath condo has a King bed & Queen sofa bed - perfect for a couple, small group, or family getaway. Located in The Appalachian, right next to Mountain Creek Resort! In the heart of Vernon Valley - near farms, trails, golf, the Appalachian Trail, and charming Warwick, NY. Plus, just 30 minutes to LEGOLAND!

Guest favorite

The exterior of a modern cabin is displayed, featuring large glass windows and a sleek black facade. A heated pool is visible with a smooth blue surface. Several lounge chairs are arranged around the pool, enhancing the outdoor relaxation space.

Cabin in Red Hook

4.96 out of 5 average rating, 365 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.

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, 128 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 heated saltwater pool is set within a gated bluestone patio, surrounded by lush greenery. The clear blue water reflects sunlight, creating a serene atmosphere. The pool area is framed by a mature tree line, providing privacy and a peaceful outdoor space.

Cottage in Kingston

4.93 out of 5 average rating, 389 reviews

Kapitan’s Cottage: Private Retreat with Salt Pool

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.

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 Mountainville

4.84 out of 5 average rating, 580 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

Home in Newburgh

4.85 out of 5 average rating, 135 reviews

Cute Apartment w POOL

I'm happy to welcome respectful guests into my home. Communication & Reviews matter to me - please share some info about yourself and the reason for staying when inquiring. *Please read the Description AND the House Rules. Let me know if you have any questions or concerns. *Please Note: No Animals** *Please mention in your inquiry if you'll have children or babies with you. My house is not baby/child-proof. If you have toddlers or children, you must keep an eye on them at all times.

Superhost

An outdoor pool is surrounded by snow-covered landscapes, with lounge chairs and tables positioned along the edge. A red umbrella stands near the pool. The area is illuminated with soft lighting, creating a serene ambiance. The backdrop features distant trees and resort buildings.

Condo in Vernon Township

4.79 out of 5 average rating, 278 reviews

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

The Appalachian is a true 4 season resort overlooking Mountain Creek Ski Resort/ Waterpark and other activities such as farms, mountain biking, multiple golf courses, horseback riding, and ziplining! NEAR LEGOLAND (25 min drive) Hike the Appalachian Trails, tour the wineries and enjoy Octoberfest/Spas/Pumpkin and Apple picking. This is a true 4 season resort with a heated(in winter) year-round OUTDOOR pool/hot tubs/Suana. Ski-in/out right to the main lift from the building

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, 173 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 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, 163 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.

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, 131 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, 144 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, 119 reviews

Retreat w/Hot Tub, 10 Min to Skiing, Fireplace/Pit

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