12 Best Airbnbs With Pool In And Near Milwaukee, Wisconsin - Updated 2024

Contributing Writer
| 5 min read

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 July 09, 2024.

1. Charming custom-built house on a hobby farm (from USD 228)

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.

Stayed at this property?
Germantown, Wisconsin, United States
22.48 km (14.0 mi) from Sky Zone Trampoline Park
86 reviews   Superhost Wifi Available
Farm stay 4 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
we loved the fireplace for a cozy night in
this place was well maintained and very clean
this tiny home exceeded our expectations a clean cozy comfortable getaway equipped with everything we needed
she is very accommodating and responsive
perfect little space with everything you'll need host was great at communicating
host was incredibly accommodating and friendly we will definitely return one day
the place was beautiful and everyone on the farm was super helpful
lara is the perfect host
extremely friendly family great location
great place to stay at very close to nearby parks for sledding and skiing
i would highly recommend this stay it’s close to multiple nice towns and things to do
very fun place to stay whether it's a trip romantic getaway
it's out in the country but still close enough to milwaukee so you the best both worlds
Read more reviews

2. Serene retreat with spectacular indoor pool (from USD 900)

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.

Stayed at this property?
Sussex, Wisconsin, United States
12.08 km (7.6 mi) from Sky Zone Trampoline Park
88 reviews   Superhost Wifi Available
ENTIRE HOME 6 Beds 12 Guests 5 Bedrooms 3 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
the size of the pool was amazing
my family had fun in the pool and the game room was fun as well
the house was amazing clean and a great place to stay
the house was clean and ready when we arrived
the project by the pool was beyond perfect and the rooms were ready and clean
thomas was very professional helpful and quick with answering and assisting me
thomas was prompt friendly and very accommodating to any issues we had
the location is good with plenty of food options
Read more reviews

3. Artsy house by Lake Mary

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.

Stayed at this property?
Twin Lakes, Wisconsin, United States
58.54 km (36.4 mi) from Sky Zone Trampoline Park
85 reviews   Wifi Available
ENTIRE HOME 13 Beds 16 Guests 7 Bedrooms 4 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
beautiful home amazing lake views and a huge pool
nice house fully stocked with great views of the lake and a huge pool
the house had plenty of space and the private pool was fantastic
best part of this place was definitely the heated pool
bedrooms were all good size with comfortable mattresses and bedding
very clean and hospitable
beautiful clean well kept house and property
the house was clean cozy and spacious
clean and fully stock with anything you might need
i had never seen a house that beautiful and clean
john is an outstanding host
avery responsive host
great location and beautiful home
the location is great close to many stores for last minute things you may have missed
definitely the right place to stay
we would definitely come back to john’s place next time we are in town
Read more reviews

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.

Stayed at this property?
Sussex, Wisconsin, United States
11.67 km (7.3 mi) from Sky Zone Trampoline Park
123 reviews   Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 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 location
cute house clean and well stocked
lisa's place was very well thought out and clean
very quiet clean and peaceful it was too cold to use the pool but we loved the option
great hospitality and adorable tiny house very clean and amenities
very cute and clean with a pool and pond
great hospitality tom and lisa are great hosts
she was super friendly and very hospitable
although we never did get to meet the hosts their personality certainly shone through
it is awesome the hosts have thought of everything to make a visit top notch
lisa and her husband were awesome hosts
all we needed was a small place and this suited our needs perfectly
an efficient economical sweet and tiny home in a quiet location with a pool and a pond
very clean in a quiet area and only about a 30 minute drive to downtown milwaukee
a terrific place to stay
i went to tom and lisa’s tiny house to utilize the pool and enjoy some quiet time
Read more reviews

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.

Stayed at this property?
Milwaukee, Wisconsin, United States
13.84 km (8.6 mi) from Sky Zone Trampoline Park
62 reviews   Wifi Available
ENTIRE HOME 4 Beds 10 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
we loved the space and the pool was as expected
the house was roomy and very comfortable for my family
the house was clean sanitized and quiet
the hosts were fast and helpful and also very accommodating to our unique needs/ requests
thanks for hosting our family
beautiful house it was pleasant (email hidden by airbnb) munication was great nice location
an amazing place to stay
great for a multiple family place to stay
Read more reviews

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.

Stayed at this property?
New Berlin, Wisconsin, United States
12.14 km (7.6 mi) from Sky Zone Trampoline Park
3 reviews   Wifi Available
ENTIRE HOME 2 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
there was ample seating on the deck with a great grill to maximize your time around the pool
large clean beautiful home just minutes from milwaukee
we picked this house mainly for the pool which was super clean
chad was an excellent host and quick to respond to messages
Read more reviews

7. Villa with a water park (from USD 181)

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.

Stayed at this property?
Lake Geneva, Wisconsin, United States
51.36 km (32.0 mi) from Sky Zone Trampoline Park
47 reviews   Wifi Available
Entire villa 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the fully stocked kitchen allowed us to prepare some of our favorite dishes
we also enjoyed being able to take advantage of room service from the main resort
everything was clean and modern
the room was clean and our stay was perfect
clean and comfortable rooms fully equipped kitchen great food on the premises
so accommodating and friendly
great location on the grand geneva property and just a few miles away from the downtown area
Read more reviews

8. Beautiful farmhouse with a fishing pond (from USD 600)

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.

Stayed at this property?
Caledonia, Wisconsin, United States
32.54 km (20.3 mi) from Sky Zone Trampoline Park
61 reviews   Superhost Wifi Available
ENTIRE HOME 8 Beds 16 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
perfect spot for a warm weekend with all the yard space the heated pool hot tub pond etc
my 2 yr old and 4 yr old loved the pool and the lake
the outdoor in-ground pool is definitely the highlight
very clean and roomy place
everything was sparkling clean and organized
some of the areas of the house are a little bit dated but very clean
clean comfortable & plenty to do host was accessible & helpful
bob was such a great host
robert was a fantastic host
he was very friendly and always very quick to respond
robert was an excellent host
great place to stay and get away great host everything in the pictures can’t wait to visit again
this is a nice place for summer get away
perfect place for our family get away
a great place to get away the retreat is true to its name
great place to take the family for vacation
Read more reviews

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.

Stayed at this property?
Sussex, Wisconsin, United States
8.74 km (5.5 mi) from Sky Zone Trampoline Park
45 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
the pool area is beautiful with outdoor furniture and lovely landscaping
nice heated pool and lots of pool toys
the beds were super comfortable
our kids loved the heated pool
water in the pool was heated and clear
the house was super clean and everything was very spelled out before hand and after arrival
the house was clean and in a nice quiet neighborhood
the house itself was super clean and very nicely updated
the pool was clean with lots of toys for the kids
the house was so clean updated private and fun
the owners were also great
james all the way through answers all questions quickly and is a wonderful host
james was a great host and was readily available if anything was needed
the owners communicate pretty well too
nice neighborhood good communication with host
it was great to have stores so close to make it convenient
the location was perfect also in that it was a calm quiet location yet near needed amenities
we loved the pool and the convenience of have a store close by
Read more reviews

10. Large house with tasteful interiors (from USD 3000)

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.

Stayed at this property?
Germantown, Wisconsin, United States
19.62 km (12.2 mi) from Sky Zone Trampoline Park
63 reviews   Wifi Available
ENTIRE HOME 9 Beds 10 Guests 5 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
we fell in love with the pictures of the beautiful home and the indoor pool
nice touch to have the bathrooms stocked with hotel style soap/shampoo amenities
my stay was very comfortable
having access to an indoor pool was the reason we booked the home and it didn't disappoint
house was great very clean and spacious
house was very clean and area was so pretty
this place is great very clean great hosts very responsive and prompt loved to stay there
host was very responsive to questions
thank you so much for being a great host
owners were nice and so attentive and good at communicating
this house is one of a kind
we were able to spend a rainy afternoon creating one of a kind pottery pieces
the neighborhood is so beautiful and quiet
the location worked out perfect for us and our family hopes we can stay here again
recommend this place to host a good size group of people if you want to be near milwaukee
Read more reviews

11. Charming house surrounded by greenery (from USD 895)

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.

Stayed at this property?
River Hills, Wisconsin, United States
25.61 km (16.0 mi) from Sky Zone Trampoline Park
39 reviews   Wifi Available
ENTIRE HOME 4 Beds 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
plenty of room for our family of 4 to spread out eat meals and play outside
the ranch-style home has a great kitchen that well stocked with anything you might need
this is a lovely house tons of space and the pool is extra special
great place easy communication everything super clean
pool was nice and clean
rooms are comfortable and the house was sparkling clean
the beds were comfy everything was super clean and we all felt immediately at home in the space
our bedroom was very comfortable and perfectly clean with lots of pillows (huge delight for us)
great hospitality host was easy to reach
host was super responsive would definitely stay there again
everything was amazing host is always available and responsive
the property is beautiful the pool was amazing and the host is very communicative
xee is a wonderful hostess and very kind and responsive
i will definitely be keeping this place in mind for any future little getaways
Read more reviews

12. Fully stocked house inspired by a renowned architect

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.

Stayed at this property?
Waukesha, Wisconsin, United States
6.41 km (4.0 mi) from Sky Zone Trampoline Park
16 reviews   Wifi Available
ENTIRE HOME 5 Beds 7 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 7

Top guest reviews
Amenities & Room:
donna has a heated pool that was pleasant even at 65 degrees outside
we enjoyed the heated pool and the backyard is peaceful
the pool and space around it was amazing
the pool area was the highlight with tasteful lighting and great energetic indoor-outdoor flow
tasteful decor throughout comfortable linens towels couches patio furniture everything i touched or sat down on was plush
really great :) gorgeous clean house with lots of room
a wonderful place to stay the home is clean and well kept and very roomy
spacious home gracious host good value
donna was a great host easy to communicate with and gracious for sharing her home with us
donna is a wonderful host she made sure everything was perfect thank you donna best weekend ever
donna communicates quickly and was helpful with area recommendations and nice touches of hospitality
donna was very prompt in all her communications and a gracious host all around
her home is a very unique gem close to a nice downtown area and other entertainment
lovely comfortable house in a quiet neighbourhood and convenient drive to the shops for supplies
lots of toys lovely home pool is amazing and it was super close to a grocery store
Read more reviews

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

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Jahz is a Philippine-based writer who enjoys solo travels as much as group adventures. She believes that life is too short to be spent living in one place, so she makes it a point to experience a...Read more

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