Are you a beer lover? Then there is no better place to drink more beer while learning about it than the city of Milwaukee in Wisconsin. Throughout its history, Milwaukee has been home to about 70 breweries and has produced several beer brands, including the renowned Old Milwaukee and Milwaukee’s Best. Today, the city’s economy is brewing with income coming in from different industries. Although progressive, the city values its rich culture and history. If you visit Milwaukee Public Museum, don’t miss a walk through the European Village. Try the local restaurants, and if you dare, take those interesting ghost tours with your mates. Whether you’re traveling for work or leisure, you can always stay in accommodations that offer modern comforts, such as a fitness center, a games room, and perhaps a private pool. Continue reading for our choices of the best Airbnbs with pool in and near Milwaukee, Wisconsin.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. Charming custom-built house on a hobby farm (from USD 160)
Immerse yourself in the tranquility of this charming 10-acre (4.05-hectare) hobby farm, where you’ll find a delightful custom-built guest house awaiting your arrival. With its inviting and fully equipped kitchen, cozy living area complete with a wood-burning fireplace, and charming loft for additional sleeping space, this open-concept retreat is a true gem.
But that’s not all – the highlight of this property is the luxurious heated pool, available exclusively from May to September for a small additional charge. Indulge in the refreshing waters and soak up the sun during your stay.
Top guest reviews
Amenities & Room:
we loved the fireplace for a cozy night inCleanliness:
this place was well maintained and very cleanthis tiny home exceeded our expectations a clean cozy comfortable getaway equipped with everything we neededHost:
she is very accommodating and responsiveperfect little space with everything you'll need host was great at communicatinghost was incredibly accommodating and friendly we will definitely return one daythe place was beautiful and everyone on the farm was super helpfullara is the perfect hostRead more reviewsLocation:
extremely friendly family great locationgreat place to stay at very close to nearby parks for sledding and skiingi would highly recommend this stay it’s close to multiple nice towns and things to dovery fun place to stay whether it's a trip romantic getawayit's out in the country but still close enough to milwaukee so you the best both worlds
2. Serene retreat with spectacular indoor pool (from USD 750)
Indulge in the ultimate relaxation and entertainment at this spacious five-bedroom vacation home, conveniently located just a short drive from downtown Milwaukee. Nestled over an acre of serene and secluded land, this retreat offers a multitude of enticing amenities. The sprawling sitting area and well-equipped game room are perfect for creating lasting memories with family and friends.
However, the real highlight awaits outdoors—a magnificent indoor pool featuring a swim-up movie projector. The pool area is a true oasis, complete with a bar and a games room for endless entertainment.
Top guest reviews
Amenities & Room:
the size of the pool was amazingmy family had fun in the pool and the game room was fun as wellCleanliness:
the house was amazing clean and a great place to staythe house was clean and ready when we arrivedthe project by the pool was beyond perfect and the rooms were ready and cleanHost:
thomas was very professional helpful and quick with answering and assisting methomas was prompt friendly and very accommodating to any issues we hadRead more reviewsLocation:
the location is good with plenty of food options
3. Artsy house by Lake Mary (from USD 907)
Are you planning a get-together? You can take up to 20 guests to this huge Airbnb house with a pool and stunning views of Lake Mary. If the weather is nice, you can try kayaking and paddle boarding as the property offers rentals and has private lake access. Or you can explore Twin Lakes and Aquanaut Ski, both of which are within walking distance.
If you prefer relaxing instead, you can lounge by the outdoor pool on the neatly lined sun beds. Please note that the pool stays open from April 15 to October 15.
Top guest reviews
Amenities & Room:
beautiful home amazing lake views and a huge poolnice house fully stocked with great views of the lake and a huge poolthe house had plenty of space and the private pool was fantasticbest part of this place was definitely the heated poolbedrooms were all good size with comfortable mattresses and beddingCleanliness:
very clean and hospitablebeautiful clean well kept house and propertythe house was clean cozy and spaciousclean and fully stock with anything you might needi had never seen a house that beautiful and cleanRead more reviewsLocation:
great location and beautiful homethe location is great close to many stores for last minute things you may have misseddefinitely the right place to staywe would definitely come back to john’s place next time we are in town
4. Fully equipped tiny house
If you’ve never been inside a fully furnished tiny house, it’s high time you book this cheerfully warm Airbnb with an outdoor pool. Here, you will have modern amenities including a kitchen, a full bathroom, and laundry facilities. You will also have access to WiFi and a smart television.
This lovely tiny house fronting the lake has access to a backyard with a garden and a hammock. There is also an outdoor pool. Guests particularly love the quiet, refreshing time they have swimming in the clean pool.
Sussex, Wisconsin, United States
11.67 km (7.3 mi) from Sky Zone Trampoline ParkAccommodates: 2
Top guest reviews
Amenities & Room:
the place is cozy extremely clean and comfortable (the bed sheets were some of the softest ever )this was just what we were looking for - beautiful yard comfy bed and the most quiet serene locationCleanliness:
cute house clean and well stockedlisa's place was very well thought out and cleanvery quiet clean and peaceful it was too cold to use the pool but we loved the optiongreat hospitality and adorable tiny house very clean and amenitiesvery cute and clean with a pool and pondHost:
great hospitality tom and lisa are great hostsshe was super friendly and very hospitablealthough we never did get to meet the hosts their personality certainly shone throughit is awesome the hosts have thought of everything to make a visit top notchlisa and her husband were awesome hostsRead more reviewsLocation:
all we needed was a small place and this suited our needs perfectlyan efficient economical sweet and tiny home in a quiet location with a pool and a pondvery clean in a quiet area and only about a 30 minute drive to downtown milwaukeea terrific place to stayi went to tom and lisa’s tiny house to utilize the pool and enjoy some quiet time
5. Family-friendly residence with a sauna (from USD 986)
This gorgeous Airbnb house with an indoor pool is spacious and features a private backyard where your children and pets can play freely. It has a family room with a pool table, a wet bar, and a ping-pong table. There’s also a smart television that is great for movie nights. For more toys or cribs, you can request the host.
Best of all, it has a decent-sized indoor heated pool. There is even a tube slide in the yard. Adults, meanwhile, can enjoy their time in the sauna.
Top guest reviews
Amenities & Room:
we loved the space and the pool was as expectedthe house was roomy and very comfortable for my familyCleanliness:
the house was clean sanitized and quietHost:
the hosts were fast and helpful and also very accommodating to our unique needs/ requeststhanks for hosting our familyRead more reviewsLocation:
beautiful house it was pleasant (email hidden by airbnb) munication was great nice locationan amazing place to staygreat for a multiple family place to stay
6. Private house close to the airport (from USD 225)
Cozy and fully furnished, this 4-bedroom private house is only a 15-minute drive away from the airport. Downtown Milwaukee is also just 20 minutes away.
There is a large outdoor pool where all four guests can comfortably swim. The pool has a ladder that makes getting in and out of the water safe and convenient. You will also have a games room with a pool table for indoor entertainment.
Top guest reviews
Amenities & Room:
there was ample seating on the deck with a great grill to maximize your time around the poolCleanliness:
large clean beautiful home just minutes from milwaukeewe picked this house mainly for the pool which was super cleanRead more reviewsHost:
chad was an excellent host and quick to respond to messages
7. Villa with a water park (from USD 141)
This one-bedroom villa features luxurious resort amenities, including access to a large outdoor pool and a water park. Previous guests loved that the pool wasn’t too crowded, leaving plenty of space to swim around or practice strokes. Here, you will have seven on-site restaurants to choose from. Alternatively, you can cook your meals in the full kitchen.
Canoeing and ziplining are available off-site while two golf courses are there within the resort. You can soothe those sore muscles afterward with a session at the on-site spa.
Top guest reviews
Amenities & Room:
the fully stocked kitchen allowed us to prepare some of our favorite disheswe also enjoyed being able to take advantage of room service from the main resortCleanliness:
everything was clean and modernthe room was clean and our stay was perfectclean and comfortable rooms fully equipped kitchen great food on the premisesHost:
so accommodating and friendlyRead more reviewsLocation:
great location on the grand geneva property and just a few miles away from the downtown area
8. Beautiful farmhouse with a fishing pond (from USD 300)
A stocked fishing pond will be right at your doorstep at this Airbnb with hot tub in Milwaukee. You can fish every day if you wish when you stay in this fully equipped house. There is a games room with a pool table and a wall-mounted television for indoor entertainment. You will also have an outdoor heated pool fronting the spacious terrace.
You can book the house all year round but the in-ground pool is available only from May 1 to October 1. If you visit during the other part of the year, you can spend relaxing hours in the indoor hot tub.
Top guest reviews
Amenities & Room:
perfect spot for a warm weekend with all the yard space the heated pool hot tub pond etcmy 2 yr old and 4 yr old loved the pool and the lakethe outdoor in-ground pool is definitely the highlightCleanliness:
very clean and roomy placeeverything was sparkling clean and organizedsome of the areas of the house are a little bit dated but very cleanclean comfortable & plenty to do host was accessible & helpfulHost:
bob was such a great hostrobert was a fantastic hosthe was very friendly and always very quick to respondrobert was an excellent hostgreat place to stay and get away great host everything in the pictures can’t wait to visit againRead more reviewsLocation:
this is a nice place for summer get awayperfect place for our family get awaya great place to get away the retreat is true to its namegreat place to take the family for vacation
9. Cozy house in a quiet neighborhood
Nestled in a quiet neighborhood, this furnished house has a large fenced-in yard. There is also a balcony overlooking the pool in the yard. You can look forward to mornings on the balcony with a cup of coffee, watching your kids happily swimming in the pool.
You will love to know that this property features an electrical car hookup for charging and a two-car garage as well as a driveway for parking. You can also book a tee time at Erin Hills Golf Course, which is 15 mi (24.1 km) away.
Sussex, Wisconsin, United States
8.74 km (5.5 mi) from Sky Zone Trampoline ParkSuperhost
Accommodates: 6
Top guest reviews
Amenities & Room:
the pool area is beautiful with outdoor furniture and lovely landscapingnice heated pool and lots of pool toysthe beds were super comfortableour kids loved the heated poolwater in the pool was heated and clearCleanliness:
the house was super clean and everything was very spelled out before hand and after arrivalthe house was clean and in a nice quiet neighborhoodthe house itself was super clean and very nicely updatedthe pool was clean with lots of toys for the kidsthe house was so clean updated private and funHost:
the owners were also greatjames all the way through answers all questions quickly and is a wonderful hostjames was a great host and was readily available if anything was neededthe owners communicate pretty well toonice neighborhood good communication with hostRead more reviewsLocation:
it was great to have stores so close to make it convenientthe location was perfect also in that it was a calm quiet location yet near needed amenitieswe loved the pool and the convenience of have a store close by
10. Large house with tasteful interiors (from USD 807)
This gorgeous house is roughly 15 minutes away from Milwaukee. It features open grounds and a tastefully curated interior with warm colors, hardwood floors, and large windows. It is suitable for families who want a quiet, relaxing time together. You will have an indoor pool with floaters that is open all year round. Kids are welcome only if there is adult supervision.
Smoking is not allowed in the pool room or any other indoor area, and diving into the pool is strictly permitted. Guests must also use the pool cover when it is not in use.
Top guest reviews
Amenities & Room:
we fell in love with the pictures of the beautiful home and the indoor poolnice touch to have the bathrooms stocked with hotel style soap/shampoo amenitiesmy stay was very comfortablehaving access to an indoor pool was the reason we booked the home and it didn't disappointCleanliness:
house was great very clean and spacioushouse was very clean and area was so prettythis place is great very clean great hosts very responsive and prompt loved to stay thereHost:
host was very responsive to questionsthank you so much for being a great hostowners were nice and so attentive and good at communicatingthis house is one of a kindwe were able to spend a rainy afternoon creating one of a kind pottery piecesRead more reviewsLocation:
the neighborhood is so beautiful and quietthe location worked out perfect for us and our family hopes we can stay here againrecommend this place to host a good size group of people if you want to be near milwaukee
11. Charming house surrounded by greenery (from USD 995)
This large, cozy house sleeps eight and sits on a 5-ac (2-ha) property surrounded by greenery. The expansive windows make the kitchen, living room, and dining room bright and airy, creating a relaxing space to come to after exploring Milwaukee.
Your family can spend joyful afternoons frolicking in the in-ground pool that is open during summer. Food and drinks are not allowed in the pool but you can dine on the furnished patio that is equipped with a barbecue grill. Also, adults are suggested to supervise children in and around the pool.
Top guest reviews
Amenities & Room:
plenty of room for our family of 4 to spread out eat meals and play outsidethe ranch-style home has a great kitchen that well stocked with anything you might needthis is a lovely house tons of space and the pool is extra specialCleanliness:
great place easy communication everything super cleanpool was nice and cleanrooms are comfortable and the house was sparkling cleanthe beds were comfy everything was super clean and we all felt immediately at home in the spaceour bedroom was very comfortable and perfectly clean with lots of pillows (huge delight for us)Host:
great hospitality host was easy to reachhost was super responsive would definitely stay there againeverything was amazing host is always available and responsivethe property is beautiful the pool was amazing and the host is very communicativexee is a wonderful hostess and very kind and responsiveRead more reviewsLocation:
i will definitely be keeping this place in mind for any future little getaways
12. Fully stocked house inspired by a renowned architect (from USD 1000)
Imagine a two-level shingled house with a paved backyard and an outdoor pool under a large shade tree. This rental inspired by the renowned architect Frank Lloyd Wright embodies exactly that. It exudes a dreamy charm that makes one feel at home. It is furnished with a small fitness center as well.
Bring your family or friends here and create summer memories together. You can easily walk to the grocery or the parks where the kids can play. Or the whole lot can spend the afternoon swimming in the private pool. The pool is open during summer, and kids are not allowed in the backyard or the pool without adult supervision.
Top guest reviews
Amenities & Room:
donna has a heated pool that was pleasant even at 65 degrees outsidewe enjoyed the heated pool and the backyard is peacefulthe pool and space around it was amazingthe pool area was the highlight with tasteful lighting and great energetic indoor-outdoor flowtasteful decor throughout comfortable linens towels couches patio furniture everything i touched or sat down on was plushCleanliness:
really great :) gorgeous clean house with lots of rooma wonderful place to stay the home is clean and well kept and very roomyHost:
spacious home gracious host good valuedonna was a great host easy to communicate with and gracious for sharing her home with usdonna is a wonderful host she made sure everything was perfect thank you donna best weekend everdonna communicates quickly and was helpful with area recommendations and nice touches of hospitalitydonna was very prompt in all her communications and a gracious host all aroundRead more reviewsLocation:
her home is a very unique gem close to a nice downtown area and other entertainmentlovely comfortable house in a quiet neighbourhood and convenient drive to the shops for supplieslots of toys lovely home pool is amazing and it was super close to a grocery store
Create some memories in Milwaukee
Take a break from work and head to Milwaukee with your loved ones. Together, you can enjoy visiting museums, historic hotels, fishing, or swimming in a pool as long as your heart pleases. Rent one of these luxurious Airbnbs with a pool and spend memorable moments together in Milwaukee.
Frequently asked questions about best Airbnbs with pool in and near Milwaukee, Wisconsin
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