Vacation rentals with a pool in Monroe

4.95 out of 5 average rating, 196 reviews

The outdoor space features a private heated pool surrounded by a stone patio. Comfortable seating options include a white sectional and lounge chairs, complemented by lush greenery and a wood privacy fence. A sunny sky enhances the inviting atmosphere of this serene retreat.

Home in Narrowsburg

Modern House with Private Pool, Hot-Tub, Fireplace

JennyRating, 5 stars3 weeks ago

This beautiful and private home was very clean, stylish and comfortable. We really enjoyed the very clean hot tub and slept well in the comfortable king bed. Anya was responsive and communicated well. Our stay was great and we would recommend this place for sure!

4.98 out of 5 average rating, 149 reviews

A spacious, circular pool is surrounded by a wooden deck, featuring two reclining chairs and a small table set nearby. Lush greenery creates a natural backdrop, enhancing the serene outdoor space, which is equipped with safety rails for easy access.

Home in West Milford

On The Rocks In The Hot Tub

DarrenRating, 5 stars3 weeks ago

Great place. loved the pool table, darts and shall shuffleboard. lots of good wineries and cider places within 25 mins. pennings is our fav. didn't use the hot tub so couldn't comment but looked nice and private. driveway is steep but easily driveable. recommended. also didn't have coffee filters and they paid for some to be delivered same day! sweet.

4.96 out of 5 average rating, 114 reviews

An aerial view captures a two-story colonial home surrounded by lush greenery. A fenced-in pool is centrally located in the yard, complemented by a brick patio and lounge chairs. The expansive landscape features manicured lawns and trees, enhancing the serene outdoor environment.

Home in Monroe

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

MeganRating, 5 stars1 month ago

The house had everything my friends and I needed. Games to play indoors, activities by the water, easy to use hot tub, kitchen and bathroom supplies. The space has plenty of room to hang out and a beautiful kitchen. Great views of the lake with a large yard. We all had a wonderful time and the hosts were kind and always respond quickly. We would love to come back for a summer trip!

4.9 out of 5 average rating, 112 reviews

Home in North Branch

Indoor Heated Pool + Sauna + Creek, Spacious 4Bdrm

DebbieRating, 5 stars1 week ago

We had a great time! My friend and I wanted to take our infants and parents on a little trip where the babies could swim a bit and we could relax and this house allowed us to do just that! The house is super thoughtful in terms of design and layout. The staircase up to the bedrooms and the bedrooms themselves (besides the master) were a little tight but completely doable. My parents loved the massage chair and infrared sauna. The pool is a great size and so convenient. The house was well stocked but I am glad we brought paper towels and a sponge to do dishes since we mostly ate in. Our only issue was with the neighborhood dogs which the house manual did mention. We just didn't expect the dogs to be outside all the time barking and even walking on the property which unfortunately scared my dog who is an anxious rescue. Nevertheless, the house is great and a comfortable space for 7 adults, 2 babies (with pack and plays), and a dog.

4.83 out of 5 average rating, 201 reviews

A private in-ground heated pool is surrounded by lush greenery and trees. The water is a clear blue, reflecting the bright sky. A spacious wooden deck offers space for lounging, while garden lights are positioned to enhance the outdoor setting.

Cabin in Swan Lake

Stunning Sullivan County Cabin w/HotTub/Spa &Pool

CarolineRating, 5 stars3 weeks ago

Our group had a great time at Anna’s place. Spacious and comfortable with great views. Anna is very responsive and gave clear check in instructions. Little communication needed given her detailed instructions, and the little communication needed- she was very responsive.

4.93 out of 5 average rating, 133 reviews

Home in New Paltz

Harrison Field Pool 10Acres BikeRailTrail 2Town

AlannaRating, 5 stars6 months ago

We had a great weekend celebrating our parents anniversary. The house was plenty big for all of us and the grounds are beautiful. Nathan was quick to respond when we had trouble navigating the AC and made sure we enjoyed our stay!

4.96 out of 5 average rating, 348 reviews

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

Modern Upstate Cabin, near Rhinebeck NY

RichRating, 5 stars4 days ago

Tina’s place is fabulous. The modern decor and architecture is beautiful. The location is peaceful and the fenced in yard was amazing; our dog loved roaming around and exploring. The outdoor space is great for grilling and sitting around the fire pit. We especially loved the kitchen. It is fully appointed and the kitchen island is incredible for prep and serving. The washer dryer combo was an excellent touch and we were able to do a couple of quick washes so that everything was clean and ready to unpack at home. Saving the best for last; the soaker tub in the master bedroom is luxurious and relaxing. Thank you, Tina. We can’t wait to visit again soon.

4.91 out of 5 average rating, 111 reviews

Home in Bushkill

Lakefront Retreat, Heated Pool, Hot Tub, Kayaks

BRIANNARating, 5 stars1 week ago

This property was an amazing value! Jennifer and Jose were incredibly communicative even before I checked in, with a full on local guide sent to me before our group arrived in Bushkill. And when issues arose during our stay they were helpful and understanding. It is a beautiful property with plenty of space for everyone. Clean bathrooms, immaculate kitchen - everything just like the photos. Can’t recommend this place enough.

5 out of 5 average rating, 5 reviews

A central living space features a spiral staircase and high cathedral ceilings supported by wooden beams. Light streams through large windows, illuminating a mix of white sofas and chairs positioned on a natural fiber rug. The open layout connects to the kitchen area in the background.

Home in Stanfordville

The Round House w/ Heated Pool

JonathanRating, 5 stars5 months ago

An amazing location when you want to get slightly off the grid for peace and tranquility. Everything you need to truly slow down, dial out and get peace, quiet and rest. An amazing spot for a weekend getaway. If you want to find yourself amongst serene surroundings and a quiet, private wooded area, this is the place. Just enough modern amenities to be comfortable, but just basic enough to make you slow down. Tanner the host was the most responsive and helpful host of any of the airbnbs we've ever stayed. Truly went above and beyond at every turn to make our stay as comfortable as possible. More than accommodating with every request.

4.98 out of 5 average rating, 116 reviews

Cottage in Eldred

Bella Cottage w/Cozy Fireplace - Spring Getaway

CarolineRating, 5 stars2 months ago

What a wonderful stay! The Bella getaway is so cozy and such a homey place to stay. The living room and kitchen are gorgeous (fully stocked kitchen -- loved it) and the main bedroom and bathrooms are nice and spacious. Only my boyfriend and I stayed so only used one bedroom but the second bedroom is nice and fits a whole queen. Such a well thought out space. So great for a couples getaway. And narrowsburg and Milford are within 30 minute drive and have such cute things to explore!! Cannot recommend more highly :)

4.95 out of 5 average rating, 354 reviews

A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.

Home in Kerhonkson

Beautiful Salt Water Pool & Fully Fenced 10 Acres

JongRating, 5 stars5 days ago

If you're looking for a stay off the beaten track this place is perfect - so much so that there is no cell signal so be warned! We even saw deer roaming the huge front yard(?) It is very child friendly, they have toys, high chair, crib and a stroller for use which reduced the amount of stuff we had to take. The only slight downside (to be expected) is the hot water tank is only 40 gallons and takes around 45mins to fill up so as a family of 5 we had to time the dishwasher, washing machine, bath time and showers carefully. Hosts are super responsive and were on hand to answer any questions.

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What guests are saying

Farm House with Built in pool/jacuzzi open in May

5 out of 5 average rating, 21 reviews1 week ago

We came for a quick girls weekend and were pleasantly surprised by how comfortable and homey we felt here. We loved going to the nearby Woodstock museum and a couple of great restaurants in the area. Sadly, the weather wasn’t great but we hope to come back sometime to enjoy all of the amenities that this home and property have to offer!

Home in Narrowsburg

What guests are saying

Stunning Mntn Views• Heated Pool• H/Tub• Sauna

4.93 out of 5 average rating, 46 reviews2 weeks ago

My friends and I had a wonderful long weekend at Susanna's home! The location cannot be beat, beautiful view and close to town with lots of cute shops and great restaurants nearby. The hot tub and sauna were amazing, the entire place was so peaceful. The perfect retreat and would definitely rent again!

Home in New Paltz

What guests are saying

The Dahlia Villa within Westerhall Gardens

5 out of 5 average rating, 23 reviews6 months ago

This is an exceptional property in every way, and provided an amazing weekend getaway for us. The design sense, amenities and attention to detail are all exquisite, inside and out. The cabin itself is lovely, somehow both modern and rustic, and the grounds with pond, landscaping and art pieces make for a lovely setting (including for dog walks). The location provides a great central hub, including hiking at Wonder Lake State Park literally 5 minutes away. We also went antiquing in Newburgh and shopping/dining in Cold Spring, both 20-30 minutes away. Lisa and Billy are considerate and friendly hosts, making clear they are available but not at all intrusive. We highly recommend this location.

Vacation home in Holmes

What guests are saying

Beaver | Pool, Firepit, Secluded, 10 acres

4.83 out of 5 average rating, 70 reviews2 months ago

We had an absolutely wonderful stay at Hava’s Airbnb! From the moment we booked, Hava was an incredible host—warm, welcoming, and unbelievably reachable. She responded to every question we had almost instantly, whether it was about check-in details or local recommendations, making the entire experience seamless and stress-free. The place itself was spotless, cozy, and exactly as described, with thoughtful touches that made us feel right at home. Hava’s communication stood out—she checked in to ensure everything was perfect without ever being intrusive. Her suggestions for nearby spots were spot-on, and it’s clear she genuinely cares about her guests’ comfort. We couldn’t have asked for a better host, and we’d love to stay here again. Highly recommend Hava to anyone looking for a fantastic Airbnb experience!

Home in Kingston

What guests are saying

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

5 out of 5 average rating, 40 reviews3 weeks ago

Absolutely Perfect Stay in Forestburgh Our stay at the Spirit Cabin was nothing short of amazing. The home is stunning, with meticulous attention to detail in every corner. The breathtaking views made every moment feel special, and the entire space was super warm with welcoming atmosphere. We brought our dog along and had the best time- BBQ, kayaking, fire pit, sauna, hot tub, and in general - enjoying the beautiful spacious surroundings. The hosts thought of absolutely everything—there was a popcorn kit, a s’mores kit, and a mini bar stocked with everything needed for hot chocolate, tea, coffee and even mixers for cocktails. Every detail was carefully considered, making our stay feel effortless and luxurious. We truly can’t wait to go back! Highly recommend this place to anyone looking for a perfect getaway.

Cabin in Forestburgh

What guests are saying

Hot Tub + Fire Pit | Spring Blooms in Narrowsburg

4.9 out of 5 average rating, 31 reviews1 month ago

I had an amazing stay at Alessandra's place! The check-in process was extremely easy, with clear instructions that made finding and getting inside a breeze. The flexible check-in option was a huge plus, and I instantly felt right at home. Alessandra's communication was outstanding—she was always responsive, friendly, and proactive. Her helpful instructions and local recommendations made my stay even better. I highly recommend staying here and would love to return.

Home in Narrowsburg

What guests are saying

Spacious Catskills Farmhouse w/ In-Ground Pool!

4.89 out of 5 average rating, 91 reviews2 months ago

This is a beautiful old house with huge windows and tons of light, beautiful views, and lots of bedrooms and hang out areas so everyone has space. The kitchen had everything we needed, the beds were comfortable and the entire place was super clean and tidy. There was a good selection of games we could play and music that our family enjoyed. It was also so nice that the house was pet friendly. The only downside was that the house was quite close to the road and my kids really wanted to sled down the hill in the backyard, but there was nothing to stop them from sliding into the road. There is hardly any traffic on the road, though, so noise was not an issue. We really enjoyed our stay here! Definitely recommend for big groups or families. We are a 7 person family - teenage kids, parents, grandparents.

Home in Grahamsville

What guests are saying

Zen Minnewaska Retreat (Entire Home)

4.94 out of 5 average rating, 36 reviews6 months ago

Enjoyed our stay very much. House was very clean and neat. Private and wooded surroundings that were especially pretty in mid-October. The foosball table was a big hit with my kids. Great location, close to Minnewaska, Mohonk, Rough Cut Brewery and not too far from New Paltz main street either. Shani was very good with communication and clear instructions. When I messaged her with a question about the heat in the house, she responded right away and solved it for us. Would stay again!

Home in Kerhonkson

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Popular amenities for Monroe rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.86 out of 5 average rating, 211 reviews

A heated salt-water pool is surrounded by greenery, with lounge chairs positioned nearby. A bright yellow rubber duck floats on the water, while the pool is bordered by textured pavers. Tall trees provide a natural backdrop, ensuring privacy and tranquil views.

Home in Woodstock

Lux Woodstock Pool/ Pvt/Fireplaces /4 mins 2 town

JoshuaRating, 5 stars2 months ago

Yanna's house exceeded all expectations. Immaculate throughout the spacious layout offered plenty of room for two families with children. My 10yo son said the bed was the most comfortable bed he ever slept in. Master bedrooms far enough apart so adults can have some privacy. Large kitchen with dining table perfect to cook and hang out. We skied at Belleayre both days (easy drive on 28) and less than 10 min from Woodstock if you want to go out. Also very close to a large grocery store. Would love to stay there again!

Home in Hopewell Junction

An inviting inground pool is surrounded by a wooden fence and shaded by lush trees. Several lounge chairs are positioned on the deck, and a colorful inflatable ring floats in the water, offering a serene outdoor space for relaxation.

5 out of 5 average rating, 18 reviews

MCM in the Hudson Valley

AlbaRating, 5 stars7 months ago

Beautiful home. Great vibes with cool art and decorations. Nearby the Fishill Farm, and the Beacon metro north. Highly recommended to stay here.

4.8 out of 5 average rating, 15 reviews

Home in Chester

Private secluded family home Hot Tub.

ManuelRating, 5 stars1 month ago

They are extremely helpful, and they accommodate all my needs. I will recommend this place to anyone.

4.98 out of 5 average rating, 60 reviews

Home in Warwick

4 bedroom house with pool (Kids & Dog Friendly)

KerriRating, 5 stars5 days ago

Our stay was wonderful, and the host was great from beginning to end! Highly recommend

4.88 out of 5 average rating, 80 reviews

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

Entire Home (private pool), Event Friendly

ChannyRating, 5 stars1 week ago

Faisal was extremely responsive throughout our stay. we loved the indoor pool and the game tables. there was a nice selection. The rooms were nice. It was great that the bedrooms were on the same floor as the living room, dining room and kitchen. We came with an elderly person and they were able to make their way around the house. my son asked if he can use the fire pit out in back and he was able to. he collected wood from the side of the house. nice location. we really enjoyed our stay.

4.87 out of 5 average rating, 46 reviews

A spacious backyard surrounds an inground swimming pool, with lounge chairs positioned nearby. Lush greenery and trees create a private atmosphere, while a blooming hydrangea bush adds a touch of color. A shaded area is provided by an umbrella over some seating.

Home in West Hurley

Hudson Valley Oasis with in-ground pool.

WedrichRating, 5 stars5 months ago

Gary and Isabelle were wonderful hosts and communicated very well and were very gracious and helpful throughout our stay. Their home is very cozy and warm and comfortable, we had a wonderful time and had everything we needed there for a great stay.!! I would highly recommend their home for a stay in the Catskills if you are looking for a place there! We’ll definitely be back there in the summer as they have a wonderful large pool in the yard to enjoy !!

4.94 out of 5 average rating, 31 reviews

A serene backyard scene is presented, featuring a sparkling pool surrounded by gray lounge chairs. Lush green trees create a privacy barrier in the background, while a garden area and fencing add to the charm of the outdoor space.

Home in North Salem

North Salem Home with Pool & Great Yard

DanielleRating, 5 stars6 months ago

This was a lovely home. Very easy getting inside. Everything was exactly as listed, pictured and described. We felt so cozy and welcomed by Susan. The house had everything you could possibly need to make your stay easy and convenient and was very clean. I had a few questions during our visit and Susan was extremely responsive and so kind. I highly recommend this home. The beds were very comfortable. Showers were very nice and had great water pressure and nice hot water. We truly felt at home and we're beyond satisfied. I highly recommend this home for anyone need of an Airbnb in the area. Lovely home and property.

4.93 out of 5 average rating, 153 reviews

A charming carriage house features large windows and a high peaked roof, set amidst lush greenery. A well-maintained pool with a gentle fountain is situated in front, surrounded by landscaped gardens and inviting white lounge chairs.

Home in Englewood

Englewood NJ Country Carriage House (15 min NYC)

VirginiaRating, 5 stars6 days ago

This was such a nice space and Lisa was a nice and accommodating host. This place is full character and wonder. Very artistic color energy in this place. We started my daughter’s 18th birthday celebration here with what is her last sleepover with friends. The hot tub, steam room and sauna were the first things and last things used. They enjoyed it so much! Thanks for your hospitality Lisa. If we ever need something like this again. We will be sure to look you up! Blessings

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Condo rentals with a pool

4.79 out of 5 average rating, 123 reviews

Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

JasonRating, 5 stars3 days ago

Henry’s place was exactly as described . The place was clean and perfect for 2 people. I would recommend staying there again.

A large, multi-story lodge showcases a vibrant exterior featuring a combination of warm yellow and deep orange hues. A steaming outdoor pool is visible in the foreground, surrounded by stonework and a railing, while the building's balconies overlook the area.

4.91 out of 5 average rating, 261 reviews

206 · Renovated Chic Premium 1 bdrm

ValerieRating, 5 stars1 month ago

The space was lovely and the hot tub access and restaurant/bar was so much fun. Can’t wait to stay again

The vibrant exterior of The Appalachian building is showcased, featuring colorful wooden siding and multiple balconies. A sparkling outdoor pool is visible in the foreground, surrounded by lounge chairs and shaded by umbrellas. Lush greenery lines the area, contributing to a welcoming environment.

4.96 out of 5 average rating, 165 reviews

One bedroom condo at Mountain Creek Resort

MelissaRating, 5 stars1 month ago

We really enjoyed our stay! The condo was VERY clean, full stocked with all of the needed essentials and in a great location right by the ski slope. Both the bed and pull-out coach were SUPER comfortable. All instructions were super clear, and the recommendations were perfect. Thank you for letting us stay at your place, we love Mountain Creek!

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.

4.92 out of 5 average rating, 111 reviews

Valley Overlook @ Mtn Creek Resort Park & Play

MollyRating, 5 stars2 months ago

My family and I had a wonderful weekend at Joe’s place. The unit was just as he described, and perfect for our needs. My older son enjoyed going snowboarding and it was great to have a space to hang out with my infant while the others were on the slopes. Joe was even able to accommodate a late checkout for us so we had a place to be with the baby while my other son was out snowboarding which was so appreciated! We will definitely be back!

The exterior of The Appalachian Lodge is displayed, showcasing a multi-story building with a combination of warm colors and architectural details. A heated outdoor pool and lounging area are visible in the foreground, surrounded by landscaped grounds and comfortable seating options.

4.94 out of 5 average rating, 835 reviews

Appalachian Lodge Top Floor w/views

Jahari LeeRating, 5 stars4 days ago

My children and I had a wonderful time! The unit was immaculate, the views were lovely, and there was plenty to do at the hotel. Paul was the best host! We had a car issue and had to extend our stay. He was polite, quick to respond, accommodating, and he took excellent care of us whenever we had any questions or concerns. We are looking forward to visiting again!

The outdoor area features a shaped pool surrounded by concrete decking. The building's facade, characterized by a mix of wood and brick, is seen in the background, with multiple large windows and balconies framed by trees and landscaped greenery.

4.96 out of 5 average rating, 51 reviews

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

CherylynRating, 5 stars1 month ago

Had a great weekend at Chris’s place! 10/10 recommend! Can’t wait to be back next ski season!

Aerial view of the Appalachian Lodge showcases a vibrant, multi-colored exterior with a central entrance. Surrounded by lush greenery, a clear swimming pool is positioned in the foreground, providing an inviting space amidst natural landscapes and mountains in the background.

4.92 out of 5 average rating, 64 reviews

Comfortable, chic, modern and sophisticated condo

KerryRating, 5 stars3 weeks ago

wonderful stay and will definitely be booking again:)

A spacious living and dining area features a large wooden table surrounded by chairs, with a cozy seating arrangement across from a fireplace. Large windows offer natural light and a view of the outdoors, enhancing the inviting ambiance of the space.