10 Best Airbnbs With Pool In Wisconsin, USA - Updated 2024

Contributing Writer
| 5 min read

Wisconsin, which is home to beautiful, diverse landscapes, flaunts massive hill stretches, scenic lakes, and lowlands. Its year-round activities and attractions draw people from across the world. Outdoor adventures, water sports, shopping, art galleries, and museums abound here. In Milwaukee, the Harley-Davidson museum features over 450 classic motorbikes, and the iconic Milwaukee Art Museum displays 25,000 art pieces. It also hosts the world’s largest outdoor music festival. Meanwhile, Apostle Islands National Lakeshore in Bayfield is comprised of 21 islands and showcases beaches, sandstone cliffs, and sea caves. For a fun-filled family outing, you can also head to Wisconsin Dells, the world’s waterpark capital. But if you want accommodations with water facilities close to these thrilling attractions, read on and choose one of the best Airbnbs with pool in Wisconsin, USA.

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 May 31, 2024.

1. Great Cedar Lodge, Merrimac (from USD 926)

Great Cedar Lodge is a 4,100-sq. ft. (380.9-sq m) rental affording an expansive grassy lawn. For quality family time, there are two spacious living rooms. Moreover, the vast indoor pool is heated and has a slide. Surrounded by windows, the stunning pool room receives abundant natural light, and guests can also jump in using the diving board for refreshing dives.

You can also cherish natural landscape views while soaking in the outdoor hot tub. There’s also a driveway with parking for six vehicles.

Stayed at this property?
Merrimac, Wisconsin, United States
54.94 km (34.2 mi) from Daggett Memorial
18 reviews   Superhost Wifi Available
ENTIRE HOME 7 Beds 12 Guests 5 Bedrooms 3 Bathrooms

Accommodates: 12

Top guest reviews
very clean comfortable and quiet
really nice home clean spacious and updated
the house was amazing and our host (tim) was very responsive and helpful with our requests
location is great - away from everything yet close enough to a state park and local communities
Read more reviews

2. Spacious house with excellent amenities, Sussex (from USD 600)

This five-bedroom house in Sussex accommodates 12 guests and is only 30 minutes from downtown conveniences. Best of all, the heated indoor pool allows swimming in any season of the year. If you need to adjust the temperature, just tell the host. The expansive pool area also features a projector and a ping-pong table.

When you’re not unwinding in the pool or spacious family room with a wide-screen TV, fun awaits in the game room with a bar. Also, the grassy lawn with a firepit makes an ideal space to spend family time. Even better, this enormous home has parking spaces for up to six cars.

Stayed at this property?
Sussex, Wisconsin, United States
115.94 km (72.1 mi) from Daggett Memorial
83 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. Gorgeous well-appointed cabin, Two Rivers (from USD 618)

This modern cabin in Two Rivers, Wisconsin, is ideal for 10 people. Nestled in lush surroundings, it offers peace and quiet away from busy city life. Its excellent amenities guarantee a comfortable stay. One of its highlights is the 1,200-sq. ft. (111.5-sq m) indoor pool with a dry spa and hot tub. Huge glass windows keep the pool area bright and afford stunning views of the woods. This extensive area also has a tiki bar, making it the perfect entertaining place.

Guests can also spend quality time in the rental’s open living area overlooking greenery. Moreover, the firepit makes a good story-telling spot over drinks. Whether you’re searching for areas for meditation, workouts, or arcade games, this place provides them all.

Stayed at this property?
Two Rivers, Wisconsin, United States
150.66 km (93.7 mi) from Daggett Memorial
67 reviews   Superhost Wifi Available
ENTIRE HOME 7 Beds 10 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
great amenities for every age (pool hot tub sauna video arcade games exercise equipment kitchen…so many things )
beautiful outdoor area as well with a fire-pit and very comfortable chairs
the pool and hot tub temps were perfect
the pool with equipped sound system through the house was highlight of the stay
very clean well managed
very clean and nice pool spacious bedrooms awesome outside area
this place is amazing it’s super clean and spacious
the big attractions (pool hot tub) also don't disappoint are super clean and absolutely great
john was very responsive to any questions
john was a great host and easy to communicate with
john is a great host and very responsive
book it you won't regret it john is a great host
john is an excellent host very attentive to our needs
great location close to the beautiful beach
the location is easy to find and is surrounded by peaceful woods
this was a great place to get away from the noise and large city area
Read more reviews

4. Eccentric pet-friendly cabin, Markesan (from USD 725)

Enjoy your getaway in Wisconsin in this eccentric pet-friendly rental offering concierge services. Although the home’s unique decor and art pieces may steal the show, it does not compromise on amenities. A laid-back indoor pool awaits your relaxation. It is surrounded by a stone fireplace and windows to keep the room bright and airy. One side also has a lengthy nook to unwind in between laps.

Moreover, there’s a custom-made 20-ft (6.1-m) bar and a well-appointed game room for entertainment. Outside, the scenic and well-maintained lawn makes an ideal place for your furry friends to play as you sit in the hammock.

Do note that the rent differs depending on the season of your booking.

Stayed at this property?
Markesan, Wisconsin, United States
10.61 km (6.6 mi) from Daggett Memorial
59 reviews   Wifi Available
Entire cabin 6 Beds 12 Guests 6 Bedrooms 2 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
the hot tub room stands out as the highlight of the house
there are 6 bedrooms and all very clean and comfortable
Read more reviews

5. The Garden of Eden, New Berlin (from USD 3650)

If you’re looking for unique accommodations, Garden of Eden is for you. The house is nestled on a tree-filed property, flaunts plant-themed decor, and has a private lake. Its unique indoor pool has been renovated and is 5 ft (1.5 m) in depth. It’s heated and opens all year round. Swimming in the distinct cave-like pool room will transport you to a totally different place.

Other facilities will keep you entertained too. You can kayak, fish, jump on the trampoline, sunbathe, and more. For a mystical rest, head to the forest-themed living area. You can book this place long-term too if a few days aren’t enough.

Stayed at this property?
New Berlin, Wisconsin, United States
126.75 km (78.8 mi) from Daggett Memorial
30 reviews   Wifi Available
ENTIRE HOME 9 Beds 16 Guests 6 Bedrooms 7 Bathrooms

Accommodates: 16

Top guest reviews
hosts were great communicators
thank you for hosting us
wow most unique and special place we have stayed
rain or shine this place is a perfect oasis for your next community event and get together
Read more reviews

6. Huge mansion with home theater, Wrightstown (from USD 550)

This waterfront mansion between Green Bay and Appleton guarantees a memorable stay. The large outdoor pool area is well-appointed with sitting areas and sunbeds. Although it’s heated and has a diving board, the pool is only available from May to November. Score some points with the pool’s basketball hoop when you’re not lazing on a floaty.

For more outdoor recreation, there’s a basketball court and a trampoline. Additionally, the spacious deck overlooking the scenery makes an ideal entertaining place. You can also head to the gym if you’re seeking to shed vacation weight. With reclining massage chairs in the theater room, experience a luxurious way of movie-watching after a good workout.

Stayed at this property?
Wrightstown, Wisconsin, United States
109.33 km (68.0 mi) from Daggett Memorial
39 reviews   Superhost Wifi Available
ENTIRE HOME 10 Beds 14 Guests 6 Bedrooms 3 Bathrooms

Accommodates: 14

Top guest reviews
- somewhat clean inside the house but could've been better
Read more reviews

7. Condo by Lake Delton with private beach access, Wisconsin Dells (from USD 65)

This one-bedroom condo along Lake Delton is ideal for young adults, couples, and solo travelers. You can walk straight to the private beach area and enjoy quiet time in front of the lake. The property also has a shared indoor pool open year-round with a hot tub next to it. You can use it any time between 8am and 10pm. Outdoors, there’s another pool with sunbeds, sitting areas, and another hot tub. Avoid bringing glasses and any high-voltage equipment to the pools.

For laundry, there’s a free washer and dryer in the unit. One parking spot is also reserved in the front lot.

Stayed at this property?
Wisconsin Dells, Wisconsin, United States
42.64 km (26.5 mi) from Daggett Memorial
131 reviews   Superhost Wifi Available
ENTIRE CONDO 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
clean comfortable and very relaxing with a great view of the lake loved it
condo was perfect with an amazing king bed that we sleep so peaceful at night
place is very clean and organized
would recommend for anyone was super clean and the host had great communication 10/10
spotless and comfortable i would recommend it and we’ll stay again
the stay was great very clean and exactly what the description said it would be
great location the place was very clean and had a nice lake view
great place to stay on the water awesome hosts thank you
even the “neighbors” were pleasant and friendly
good communication with host
communication with the host was prompt and very helpful
chris was also super helpful and accommodating we will be coming back
close to many dells attractions
great location and property for the price
great location very nice getaway spot
such a perfect location if wanting to stay near the dells beautiful right on the lake
the location was surprisingly secluded for being so near all the fun and very beautiful
Read more reviews

8. Renovated three-level house, Allouez (from USD 456)

This three-level house on a grassy hill has been recently renovated and showcases modern details. It allows parking for up to five cars and is close to conveniences, including the airport. The indoor heated pool is available year-round and found in a brightly lit room with a grass-covered wall. You can swim there any time of the day and enjoy the provided floaties.

Outdoors, the back lawn with a firepit and the spacious deck can be used for entertaining. Children will also enjoy the arcade game room with an array of games. You can spend fun family time in the cozy theater or the bright and spacious living room.

Stayed at this property?
Allouez, Wisconsin, United States
128.14 km (79.7 mi) from Daggett Memorial
189 reviews   Superhost Wifi Available
ENTIRE HOME 8 Beds 14 Guests 6 Bedrooms 4 Bathrooms

Accommodates: 14

Top guest reviews
Amenities & Room:
amazing place with lots of space bedrooms and a pool
the arcade and huge pool is great for people of all ages
we loved the pool the massage chair and the arcade in the basement
the pool was much larger than we expected…lots of entertainment for everyone
the pool was nice and warm
the house was clean and spacious
the house is clean and everything you need is available
house was clean and included all of the necessities
the house was so spacious and so clean
the house is huge perfect for sharing with lots of people clean and tom was excellent with communication
the host was really responsive
we had a great staff retreat
tom the host is responsive and kind
the house was nice host was attentive and responsive
will definitely want to host another event there
good location near a ton of fun things
this place is great for families with kids or just to take an adult trip
you couldn’t ask for a better place than house whatever age
Read more reviews

9. Tree Top House, Milton (from USD 175)

The pet-friendly Tree Top House spreads over 10.5 ac (4.2 ha) in Milton. The property offers three walking trails and is 3 mi (4.8 km) from shopping and dining options. After an adventurous day out, a relaxing mini pool indoors makes a beautiful retreat. It is heated and right next to a large window affording lush nature views. Ensure you attend to your children while they’re in the pool.

You can also use the sauna to relax. Meanwhile, the spacious furnished deck is perfect for long talks with your loved ones. Do note that this private and peaceful home does not offer Wi-Fi.

Stayed at this property?
Milton, Wisconsin, United States
118.26 km (73.5 mi) from Daggett Memorial
189 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the pool was honestly perfect for our 7 and 2 year old
the deck is awesome after relaxing in the pool and sauna
just as fantastic the second time around sub zero temperatures outside didn't keep us from being warm and cozy
the sauna was a great addition for the adults and my toddler had a blast with the pool
comfortable and quiet bedrooms
comfortable and clean
it was extremely clean and well stocked with the necessities
it was quiet and secluded and very clean
absolutely beautiful home very clean and the sauna was such a treat
an artful and peaceful retreat super clean and well-cared for
host was great and communicated well
close to stores but secluded enough for a nice quiet getaway
this spot was the perfect location for a small getaway with friends
this place was the perfect thanksgiving get away for the entire family
i’m sure this place is even more beautiful in the summer or warmer weather
wow this place is one of the most unique airbnbs i’ve ever stayed at
Read more reviews

10. Guinness Stilt Lodge, Jim Falls

Guinness Stilt Lodge, built by a Guinness World Record holder, provides excellent amenities for a luxurious stay. Located near Lake Wissota, it will give you access to water adventures, including canoeing, kayaking, and boating. Trees surround the free-form outdoor pool, making it an excellent spot for chilling amid nature. It also has a slide so that you can splash into the water.

Moreover, you can enjoy the home theater during your downtime or use the sauna to sweat away your worries. The spacious deck on the upper level also affords beautiful views of the river and nature. While indoors, remember to keep your shoes off.

Stayed at this property?
Jim Falls, Wisconsin, United States
208.09 km (129.3 mi) from Daggett Memorial
60 reviews   Wifi Available
Entire cabin 5 Beds 15 Guests 5 Bedrooms 3 Bathrooms

Accommodates: 15

Top guest reviews
Amenities & Room:
house was incredible pool and patio were so cool
the outdoor kitchen is so nice to grill out and sit by the river
the home was beautiful the pool was great & warm and the views were amazing
loved this space for our staff team connection time large spacious rooms were comfortable outdoor spaces beautiful
tons of spaces - living room movie room games area bar - to spread out and enjoy
the house stays super clean because of that
cabin was super clean and beautiful we had zero issues while there
check-in & out was simple decor and cleanliness was great
everything was clean and the kitchen was stocked with all cooking tools we needed
the house itself is roomy comfortable and clean with plenty of areas for relaxing mingling eating etc
this could be a really awesome place if the host can work out the issues with her management company
location was great for a weekend getaway
really great location and large space with plenty of room
the location was beautiful and pool was perfect with kids
great location lots of room nice backyard
excellent location excellent place and hospitable host
Read more reviews

Fantastic Airbnbs for your getaway in Wisconsin

Enjoy your getaway in Wisconsin while living in a fantastic rental. Come home to a relaxing pool after a day filled with the experiential treasures of this beautiful state. Choose from one of the best Airbnbs with pool in Wisconsin, USA, above!

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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Kipangwala believes that traveling serves as both a teacher and a source of gratification. She is inclined to learn about the cultures of the places she visits, and her travels foster gratitude, a...Read more

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