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.

1 of 1 pages1 / 1
Top guest favorite
An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.
Home in New Paltz
4.88 out of 5 average rating, 225 reviews

Scenic River View Escape | New Paltz

Unwind in nature at this scenic New Paltz escape, located on a serene riverbank with spectacular views. Large porch and private backyard are perfect for relaxation and stargazing. Recently renovated, the house blends modern amenities with a tranquil atmosphere. Thoughtfully designed, it features a cozy fireplace, large smart TV, and fully equipped kitchen. Explore nearby hiking trails, waterfalls, and Minnewaska State Park, or relax in the hot tub. Ideal for couples, families, and remote workers

Guest favorite
The image features a clear, inviting pool in the foreground, with the country home visible in the background. Surrounded by lush greenery, the house has a deck and large windows, blending harmoniously with the serene wooded landscape.
Cottage in Eldred
4.98 out of 5 average rating, 132 reviews

Bella Cottage w/Pool, BBQ - Catskill Getaway

** Pool opens May 8 weekend! It is an above ground heated pool, the temp preset to 84 Disconnect, relax and rejuvenate in this cute country home! Enjoy the serene, wooded surroundings as you watch deer trot by and end your day unwinding under starlit night skies. This 2-acre gem is tucked away on a private drive, just off the main road. Though secluded, grocery stores and restaurants are just down the street. The house is equipped with all the modern amenities to make your stay comfortable.

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, 382 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. 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, 139 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
Cottage in Livingston Manor
4.96 out of 5 average rating, 167 reviews

Cozy Cottage w/ Pool+Jacuzzi+Sauna+ Reading nook!

This lovely cottage sitting on almost 3 acres of wooded land is nestled perfectly in the gateway to the Catskills region. It’s a wonderful getaway from the city to recharge, relax and enjoy the nature that is readily available. The pool, hot tub and the newly installed sauna are the perfect setting to enjoy the serenity of a relaxing day or evening. You can enjoy cooking, reading in our cozy reading nook, bbqing, hiking or many other activities that the Catskills region is famously known for.

Guest favorite
A charming red barn-style house is framed by a vibrant field of wildflowers. Various hues of blue, red, and white blossoms create a colorful foreground, while lush greenery surrounds the property, contributing to a serene natural setting.
Barn in Katonah
4.96 out of 5 average rating, 139 reviews

Magic Red Barn with Heated Salt Pool (opened now)

Escape to magic, just one hour from NYC. No car really necessary. Immerse yourself in nature’s wonderland: wildflowers blooming in June, scenic trails, and vibrant local farmers’ markets. Unwind in a heated saltwater pool and cedar soaking tub. Sleep in a stunning renovated loft — 1,000 sq ft of luxury in a private barn. Ideal for family or friends: 1 king, 2 queens, and a toddler bed. Full kitchen with oven, microwave, and half fridge. Fiber optic Wi-Fi. Privacy guaranteed: no other guests.

Top guest favorite
An in-ground swimming pool is surrounded by lush greenery, offering a serene outdoor escape. Lounge chairs are positioned on the pool deck, inviting relaxation. The area is accented by planters, creating an inviting and enjoyable outdoor space.
Home in New Paltz
4.98 out of 5 average rating, 539 reviews

midcentury mod * POOL * walk out trail R2R /TOWN

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 & HOT TUB short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk to an organic farm? A scenic mile to R2R trail to Mohonk, Water St. mkt & the Village of NP WHOLE PLACE IS YOURS HOUSE & PROPERTY POOL May 1 -Sept 30 HOT TUB YEAR ROUND

Top guest favorite
A wooden lounge chair is positioned near a serene saltwater pool, surrounded by lush greenery. The pool's clear water reflects the inviting outdoor space, which is complemented by concrete paving and a manicured lawn.
Home in Cottekill
4.96 out of 5 average rating, 302 reviews

Peace & Privacy - High Falls (hot tub & salt pool)

Enjoy the serenity of this contemporary home on six private acres central to all the Hudson Valley has to offer; just 20 min. from the NYS Thruway. Year-round hot tub, seasonal salt water pool, fireplace, gourmet kitchen, and large deck & patio w/ fire pit make this the ultimate getaway. Sports enthusiasts, shoppers, and diners will delight in how close we are to amazing Catskills attractions. New Paltz, Kingston, Mohonk Preserve and Minnewaska State Park are just 15 minutes away.

Top guest favorite
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, 177 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
An inviting backyard features an inground pool surrounded by a spacious patio area. Loungers are positioned alongside the pool, and a diving board extends over the water. A fenced perimeter provides privacy, with lush greenery adding a natural backdrop.
Home in Sussex
4.93 out of 5 average rating, 101 reviews

Mountain Creek retreat PH w/pool & hot tub

⸻ Welcome to The Spruce, a privately owned, modern farmhouse retreat less than 5 miles from Mountain Creek Ski Resort in Vernon, NJ. Relax in your private backyard oasis with a fenced-in pool, 6–7 person hot tub, two decks, BBQ grill, and outdoor fireplace. Explore nearby wineries, breweries, farms, and the charming town of Warwick, NY—just 15 minutes away. Whether you’re visiting for adventure or relaxation, The Spruce offers the perfect balance of comfort and luxury.

Guest favorite
A serene pool area features a deep blue unheated swimming pool with steps leading in. A gazebo, softly illuminated by string lights, is nestled among lush greenery in the background. The natural landscape creates a tranquil retreat.
Apartment in Chester
4.98 out of 5 average rating, 160 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 15 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
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
4.95 out of 5 average rating, 123 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.

Popular amenities for Monroe rentals with a pool

  1. Airbnb
  2. United States
  3. New York
  4. Orange County
  5. Monroe
  6. Rentals with pools