Wisconsin, known for its delicious cheese and historical places, is a great place to visit. If you’re up for some scenic trips, you might want to visit Devil’s Lake State Park, Lake Michigan, and Lake Superior to witness some magnificent water views or check out places for snowboarding in the state. You can even explore some engaging outdoor activities such as hiking and rock climbing. To learn about art and innovation, head to Milwaukee Art Museum and Harley-Davidson Museum in Milwaukee. Meanwhile, nature enthusiasts can visit Olbrich Botanical Gardens, which houses a rose garden and a gilded Thai pavilion.
If you want to take your vacation to the next level, consider Wisconsin as your next destination. If you want to elevate your experience, you can rent a vacation house with a lovely swimming pool. Read further to see the top vacation rentals with private pool in Wisconsin.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on October 27, 2025.
1. Lakeview getaway with outdoor decks in Lake Geneva (from USD 30199)
The whole family can soak in the marvelous view Lake Geneva has to offer because this vacation rental is only a 2.8-mi (4.5-km) drive from downtown. This Airbnb features an outdoor natural pool with a waterfall. It’s open from Memorial Day through Labor Day. This natural stone pool is 13 ft (3.96 m) in length and 11 ft (3.35 m) in width and has a depth of 3 ft (0.91 m). Moreover, you can fully enjoy the tranquillity of nature at this cabin-like home that can accommodate up to eight people.
It has four spacious bedrooms with five beds and three bathrooms. Dive into its unique sitting pool and play with the pool table and board games that can keep everyone entertained. Note that pets are not allowed, and drop-in guests are strictly prohibited.
Lake Geneva, Wisconsin, United States
51.2 km (31.9 mi) from Kayla's PlaygroundSuperhost
Accommodates: 8
Top guest reviews
Location:
a bit rigid but a nice placeRead more reviewsCleanliness:
lots of nice touches clean place
2. Secluded paradise with a hot tub in Somerset (from USD 2281)
With three bedrooms and six cozy beds, ten guests can surely have a comfortable stay. This house rental with an indoor pool in Wisconsin features a hot tub that guests can take advantage of. The kids can slide to the pool and enjoy the trampoline. Teens and sporty ones can also play volleyball, badminton, and basketball. For guests who just want to chill, a disc golf course and massage chairs are also available.
Somerset, Wisconsin, United States
451.42 km (280.5 mi) from Kayla's PlaygroundAccommodates: 12
Top guest reviews
Host:
kelly is a wonderful hostkelly was a wonderful hostkelly is a fabulous hostkelly was super responsive to questions we hadkelly is a great hostLocation:
such an amazing break from reality lovely placeour family wanted a place to get away and this was the perfect spotit was the perfect escape (and such a close drive from our minneapolis home)kelly’s place is the perfect distance for a relaxing getaway from the citiesa perfect place for a family get togetherCleanliness:
it was sparking clean and well equippedvery clean and beautiful perfect spot for any eventextremely clean and comfortable and the property was amazingthe place was clean spacious and welcomingthe house is very clean and has so much to doRead more reviewsAmenities & Room:
(by the way the wifi is excellentgreat amenities incredible kitchen and plenty of spacethe gator jeep hot tub pool and steam shower are the bestthe pool hot tub in-ground trampoline fire pit etc were in perfect conditionthe pool and hot tub are amazing
3. Newly renovated home in Hager City best for families (from USD 650)
Settle into this newly renovated property with the breathtaking view of the Mississippi River that can be seen from all rooms. Even if you are surrounded by nature, you can stay connected through the complimentary WiFi access. Take advantage of the outdoor pool and allow yourself to have a relaxing swim. The entire modern house is fully furnished and is the perfect getaway from the city’s busy life. With its three spacious bedrooms, it can accommodate up to six guests. You can also savor kebabs with the outdoor barbecue grill.
Hager City, Wisconsin, United States
415.46 km (258.2 mi) from Kayla's PlaygroundAccommodates: 6
Top guest reviews
Host:
stunning comfortable and host was available and responsivebook while you can because this was one of a kindLocation:
the neighborhood is quiet and quaint and perfect for a little getawayCleanliness:
beautiful clean and well stocked homethe pool was heated and clean and overlooking the riverRead more reviewsAmenities & Room:
the top appliance kitchen was a dream come true for my chef-like husbandthe natural light flowing through every room was inspiringi loved sitting in all the different rooms and taking in the viewsthe house is decorated beautifully and spacious the beds are comfortable and the views are spectacularfurniture is so comfortable beds are cozy and showers and tubs are amazing
4. Luxurious house with heated pool in Milwaukee (from USD 986)
Spend your vacation in this luxurious home with an indoor heated pool and sauna, complete with free essential oils. It can house up to ten guests with four bedrooms and five beds. The heated pool can be enjoyed by both kids and adults, for it has a depth of 9 ft (2.74 m) at the deep end and 3 ft (0.91 m) at the shallow end. You can use the pool toys, goggles, and towels provided here.
This lively accommodation has a recreation room with a pool table. With an additional pet fee of 50 USD, your furry friends can also join the fun and roam around freely in the large yard. The modern kitchen has pans and a stove you can use to make your own meals, and if you want to cook outside, there is a gas grill and a gas fire pit.
Milwaukee, Wisconsin, United States
13.3 km (8.3 mi) from Kayla's PlaygroundAccommodates: 10
Top guest reviews
Host:
the hosts were fast and helpful and also very accommodating to our unique needs/ requeststhanks for hosting our familyLocation:
beautiful house it was pleasant (email hidden by airbnb) munication was great nice locationan amazing place to staygreat for a multiple family place to stayCleanliness:
the house was clean sanitized and quietRead more reviewsAmenities & Room:
we loved the space and the pool was as expectedthe house was roomy and very comfortable for my family
5. Beautiful home with a private outdoor patio in Eau Claire
Enjoy yourself in this home, where you can immerse yourself in the refreshing waters of an indoor heated pool, meticulously maintained at a comfortable depth of 4 ft (1.22 m), ideal for leisurely swims or a splash with family and friends. The indoor pool can be accessed from the kitchen and hallway and the entry points have locking doors and alarms to provide an added degree of security and a worry-free experience. The pool area itself is a paradise of delight, complete with a table and chair set where you may gather with family and friends.
Furthermore, with amenities such as an electric fireplace and a 65-inch smart TV, the main living space welcomes you with warmth and refinement. Head to the private outdoor patio, a quiet haven ideal for grilling or relaxing in the open air around the gas fire pit.
Eau Claire, Wisconsin, United States
353.94 km (220.0 mi) from Kayla's Playground
6. Lakefront mansion in Oconomowoc
Lakefront living awaits at this three-level Summit mansion that features a pristine lakefrontage with a private beach and pier. The huge dwelling has six masonry fireplaces found in the elegantly designed living room and dining room as well as the spacious gourmet kitchen. For an immersive lakeside experience when staying in, the property features a conservatory and sunroom. Apart from spacious bedrooms, the upper floors also include a game room with a billiard table, playroom, and media room.
Additionally, the property has an in-ground pool and a seven-person hot tub for your soaking pursuits. Located in a private mountain estate, this rental also affords to offer a tennis court. Note that the posted rates are for seven-night stays and will have to be manually edited by the host when booking for less than seven days.
Oconomowoc, WI, US
7. Timeless retreat in Green Lake County
At this timeless vacation home beside Lake Puckaway in Green Lake County, you can enjoy a meticulously maintained private estate and a custom-built indoor heated pool with a swim-up fireplace. The whole pack can soak in the hot tub-like pool, which is 20 ft (6.10 m) long and 6 ft (1.83 m) deep, or the hot tub. It also has temperature control, air jets, and mood lighting. The house is sprinkled with stained glass details throughout as seen in the fully equipped kitchen, two separate dining areas, and covered patio with grill and pool table.
The splendor continues on the second floor which features six bedrooms with private access to a wrap-around porch with swings and day beds. You’ll also find a fireman’s pole on the porch that leads to the pool area. Other notable rooms here include the game room where you can enjoy a bar, antique jukebox, piano, pinball, and slot machine as well as a great lounge room where you’ll have the comforts of a fireplace and several exotic and antique taxidermy pieces.
Wisconsin Dells, Wisconsin, United States
167.95 km (104.4 mi) from Kayla's Playground
Top guest reviews
Host:
i can tell you this it’s true this home is one of a kindthe maintenance guy tom was very nice and helpful as wellRead more reviewsAmenities & Room:
the wrap around deck with all the various swinging beds and chairs was amazingthe bar room was awesome with lots of games to entertain everyone
8. Luxury villa with a hot tub and pool in Krakow
If you’re looking for a place to relax and recharge in Wisconsin, here’s the perfect vacation rental for you. The rustic setting with lots of green all around makes it the perfect place to escape the stresses of your everyday city life. If you’re the outdoorsy type, recreational activities are nearby including birdwatching, hiking, snowmobiling and skiing (seasonal, of course), biking, fishing, and more.
This Wisconsin vacation rental with a private indoor heated pool is designed with that classical cabin vibe to add to that rustic appeal. It is also equipped with all modern conveniences to ensure your stay will be as relaxing as possible. Some of the amenities to enjoy include a private sauna, hot tub, and yoga sunroom. It can accommodate up to 10 people, making it a great getaway for families and groups of friends.
Krakow, Wisconsin, United States
209.88 km (130.5 mi) from Kayla's Playground
Top guest reviews
Host:
ava was quick to respond to our concerns and seemed very kindCleanliness:
it was clean welcoming and spaciousRead more reviewsAmenities & Room:
the beds were very comfortablequiet secluded getaway with comfortable beds and linens with a perfect pool and hot tub
9. Spacious home with an indoor pool in Green Bay
If you’re planning to host a get-together with a large group of people, either with your family or friends, this amazing vacation rental is the perfect place to entertain your guests. This spacious and modern home has six bedrooms, four full baths, a fully equipped kitchen, a living area, and lots of other indoor spaces to accommodate up to fourteen people. The property also features an indoor pool heated round the year, a poker table, a game room with arcade games, and a 100-inch movie screen in the basement to offer various entertainment for all ages.
Furthermore, the large open-air backyard features a fire pit area with cozy seats and greeneries all around, the best spot to enjoy the great outdoors while having some drinks with the gang.
Green Bay, Wisconsin, United States
176.42 km (109.7 mi) from Kayla's Playground
Top guest reviews
Host:
we all had a great time thanks tom for hosting usCleanliness:
home was very clean and had sanitizing and cleaning supplies availablethe pool is awesome: clean not heavily chlorinated lots of fun toysrooms are on all 3 floors and were clean with ample linenshome was clean has open floor plan and lots of sunlightRead more reviewsAmenities & Room:
we enjoyed the large heated pool fun arcade games and appreciated the tea/coffee stationthe pool was super warm and there were various water toys and floatieshuge living room for gatherings and gamesthe beds were extremely comfortable and the family area was spacious enough for everyonethe kitchen allowed for family cooking and the area also includes a good selection of deliver-in options
10. Lakefront holiday home best for families in Newton
One of the best holiday home rentals you’ll find in Wisconsin is right in the heart of Newton. This magnificent lakefront property is a five-bedroom home that can sleep up to sixteen people. The lake house has a well-maintained, picturesque yard with a heated swimming pool that overlooks the waters of Wisconsin. It also has a water slide and fountains. If you’re visiting in the winter, there’s also an indoor pool that you can enjoy!
All in all, this gorgeous home has plenty of recreational facilities, such as an indoor basketball court and a playground, to keep all guests entertained.
Newton, Wisconsin, United States
123.48 km (76.8 mi) from Kayla's Playground
Top guest reviews
Host:
the owners were warm friendly and made sure that we had an exceptional timethe property managers were extremely kind and helpfulRead more reviewsAmenities & Room:
the pool was great for the kids heated
11. Well-furnished retreat with nature views in Ripon
If you’re looking for a beautiful home tucked in the middle of towering trees and lush greens, this property is located in Ripon and is just minutes away from the shores of Green Lake. Besides the indoor pool with a slide, the other amenities available at this vacation house are the television with satellite and cable, the full kitchen, free access to Wi-Fi, and a spacious deck overlooking the trees and the surroundings.
With 6 bedrooms, groups of up to 16 people can comfortably stay here.
Ripon, Wisconsin, United States
127.67 km (79.4 mi) from Kayla's Playground
Top guest reviews
Host:
owners were great hoststhe hosts were fast and helpful and also very accommodating to our unique needs/ requeststhe owners went above and beyond to make our stay as comfortable as possiblethe owners were very responsive and helpful to make the weekend as enjoyable as possible for usjennifer and kevin were great hostsRead more reviewsCleanliness:
bright clean plenty of room for groups
12. Family-friendly luxury home with hot tub in Hudson
In the middle of Hudson, Wisconsin, is where you’ll find this spacious home that features an outdoor heated pool with plenty of seating area and a grill. Coming as a large group should not be a problem since a total of 20 people can be comfortably accommodated in this 5-bedroom home.
You can whip up your feast at the contemporary kitchen or the outdoor grill. Some unique amenities at the property are the trampoline, wiffle ball field, playground, and hammocks. The place is ideal for family vacations since there are plenty of recreational facilities for the little ones to enjoy.
Hudson, Wisconsin, United States
443.34 km (275.5 mi) from Kayla's Playground
Top guest reviews
Host:
jason was a great host prior to check-in he was responsive to questions and easy to communicate withthe owner communicates well and ensures you have a good stayjason was very accommodating starting with check-in jason was very flexible and gave us a full tour upon arrivalCleanliness:
the house itself was very clean and more than accommodated our group of 10Read more reviewsAmenities & Room:
the backyard was a dream set up for fun with a pool hot tub and yard gameskitchen dining room large and nice living roomthe pool hot tub and outside patio very niceplenty of space and activities for adults plus 10 little kids to swim and play outside
13. Spacious getaway with hot tub in Madison
For larger families and groups, this home might be the perfect rental for you. It can accommodate up to 16 people with its 5 bedrooms with king and queen beds. The place also has two large couches and six reclining chairs for you to lounge on.
The kids can surely have fun with the outdoor ground pool because it has a diving board and a slide. It’s heated, so you can use it in all seasons. Guests who don’t wish to swim can unwind on the sun loungers. There is a karaoke machine that you can use so you can sing your heart out while you enjoy some snacks. The hot tub and large deck with a grill are also available for your enjoyment.
Madison, Wisconsin, United States
126.49 km (78.6 mi) from Kayla's Playground
Top guest reviews
Host:
the owners are lovely and walked us through everythingthis home had everything owners were wonderful and property was spotlessjulie the host is very nice and extremely responsivehosts were great and the home was clean and had pretty much anything you would needowners were great and the home was clean and organizedLocation:
walking distance to a great parknice home good communication and very close to epicgreat property great hosts we really enjoyed our time here the pool was great and the location convenient to everythingeverything in place for a perfect family stayCleanliness:
we didn’t use the pool but it looked clean and funthe house is very clean and spaciousthe house is beautiful clean spacious and everything we had hoped forthe pool and hot tub were very clean and well heatedRead more reviewsAmenities & Room:
the pool is amazing (and doesn't have the harsh chlorine - huge bonus)
14. Exclusive property with hot tub and heated pool in Caledonia
This home’s 3 large bedrooms can sleep up to 20 people. You can also pitch tents and camp outside for a more outdoorsy experience. Featuring a newly created garage recreation room where you can play pool and ping pong, you and your family or group of friends can enjoy your stay here. The property has an entertainment area with a 110-in widescreen and a projector for movie marathons.
An outdoor pool is also available should you want a relaxing dip. It’s heated and open from mid-May to mid-September.
Caledonia, Wisconsin, United States
7.28 km (4.6 mi) from Kayla's Playground
Top guest reviews
Host:
the owner is very easy to work with as wellrobert was the most gracious host we’ve had yetrobert was so helpful and easy to communicate with before and during our stayLocation:
i highly recommend this location"the retreat was an outstanding place for a five day trip to wisconsinCleanliness:
easy check-in everything clean and great location just off the i-94 exitlarge great room clean kitchen and sleeping spaces when we finally went insideRead more reviewsAmenities & Room:
large well taken care of yard and nice pool and hot tubthe game room/garage was perfect
15. Tranquil accommodation on Lake Michigan in Kewaunee
This spacious and tranquil abode on Lake Michigan, just outside the small harbor town of Kewaunee, gives you rural-life vibes while providing all the luxe comforts and contemporary amenities of an upscale property. Its highlights include the expansive lake views from its backyard with a fire pit, hammock, cedar swing, and a 24-ft (7.3-m) raised pool. The latter can be heated from June to August.
When staying in, you’ll enjoy the conveniences of an open-plan interior comprising a spacious kitchen facing the lake, a family room with a gas fireplace, and a sizeable dining table. There’s a recreational room, too, on the lower level and free WiFi and cable TV for your modern entertainment needs. The property makes your stay worth it with the benefits of a deck with a gas grill and an outdoor hot tub.
Kewaunee, Wisconsin, United States
174.61 km (108.5 mi) from Kayla's Playground
Top guest reviews
Host:
steve was the perfect hostthe owners are super nice and very easy to communicate withand the sunrises glorious the owners were very attentive to our needsLocation:
our 2021 annual family gathering found a perfect location here in kewauneeCleanliness:
big clean swimming poolRead more reviewsAmenities & Room:
the bathrooms are in great shape and stocked with linens
16. Spacious abode with a game room in Arkdale
Comfort, fun, and relaxation all come together in this spacious and welcoming home, thanks to amenities including the indoor pool, which guests of all ages can enjoy. Allow the water of this heated pool to embrace you while you swim or float while taking in the relaxing atmosphere.
Each bedroom in this house has its flat-screen TV and a sound system with a CD player for those who want to relax to some music in their own space. Enjoy some friendly competition on the pool table in the game room. Stepping outside, you’ll find a paradise for outdoor gatherings, complete with picnic tables where you can eat meals in the open air, grills where you can taste the savory flavors of barbecue, and a fire pit to gather around as the sun goes down.
ARKDALE, Wisconsin, United States
210.67 km (131.0 mi) from Kayla's Playground
17. Beautiful vacation home near the lake in Plymouth
This chateau can accommodate up to 10 people. You can have a majestic view of the nearby Elkhart Lake. Swim in the in-ground pool with lighting and take amazing pictures. The place features a pond you can marvel at. You can also watch some lovely animals such as deer, turkeys, pheasants, or bald eagles roaming freely in their natural environment. Visit nearby attractions such as Wade House Historic Site and shop at a farmers’ market available every Saturday morning.
Plymouth, WI, US
18. Luxurious family home with hot tub in Burke
This three-bedroom home can easily accommodate up to eight people, making it an ideal home for families. The place features a spacious hot tub, and there is also an indoor pool you can freely swim in. This Wisconsin vacation rental with a private indoor pool is only 15 minutes away from Capitol Square. With its vast yard, hammock, and gas grill, you and your family can certainly enjoy a lovely bonding time.
109.55 km (68.1 mi) from Kayla's PlaygroundAccommodates: 10
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Host:
the hosts were friendly and responsiveit was a great comfort that our hosts were very attentive to our questions and needsLocation:
plus great location (secluded but only a few minutes away from downtown)great place for our getaway close to everythingCleanliness:
clean and communication was excellentcomfortable beds beautiful gazebo very clean and reasonablethe house was very clean and great communication with the ownerhouse was clean with good amenitieswe so enjoyed gathering is this beautiful space the kitchen was well stocked and clean as well as eco-friendlyRead more reviewsAmenities & Room:
we loved the pool and hot tub the deck was perfect for dinner snacks and drinkingwe truly enjoyed the spacious deck area swimming pool and hot tubwith pool cabana and hot tub; it was a relaxation retreat we neededthe kitchen is well furnished and the hot tub was amazing
19. Cozy getaway with a fireplace in Whitewater
This private vacation rental is a great place to unwind away from all the troubles of everyday life. It sits on a large property with lots of trees all around. It’s quite close to Whitewater and Rice Lakes, which means there are plenty of fishing, kayaking, hiking, and sightseeing opportunities nearby. There’s also a pool in the backyard if you just want to enjoy a relaxing swim.
The house is big enough to accommodate up to six guests. The spacious open-concept kitchen features granite countertops and stainless-steel modern appliances to ensure seamless food preparation. The main living room has cozy seats and a stone fireplace, the perfect spot to relax and enjoy conversations with your family or friends. There’s also a pool table, poker table, and large smart TV for some indoor entertainment.
61.79 km (38.4 mi) from Kayla's PlaygroundAccommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Host:
the owner was great she response to any question or concenrs very quicklyit was a peaceful friendly stayLocation:
great house for couples with a under 1 minute walk to rice lakeCleanliness:
very clean and privatethe house was roomy clean and comfortable and the grounds were really niceRead more reviewsAmenities & Room:
the master bedroom lights had to be on in order to use the ceiling fanthere was plenty of family space and the kitchen was great
20. Pet-friendly home with lake views in Twin Lakes
This grand home can accommodate up to 24 guests with its 8 bedrooms, including the pool house. You can have a lovely swim in the heated in-ground pool. However, note that the pool is open seasonally, open from a few days before Memorial Day and shutting by Labor Day.
The property is near a private lake that you can explore as well. You can try different water activities such as kayaking, canoeing, and paddleboarding. Pets and events are allowed so you can have more fun while you stay in this accommodation. If you feel like going out, you can visit nearby places such as Wilmot Mountain and Mountain Falls Water Park.
46.9 km (29.2 mi) from Kayla's PlaygroundAccommodates: 24
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Host:
the property owner was helpful and quickly answered any questions we hadCleanliness:
we had been promised an extremely clean house with covid concerns and we did not get thatRead more reviewsAmenities & Room:
everyone loved using the heated pool
Have a great poolside vacation in Wisconsin
With plenty of things to do, breathtaking nature views and historical places to offer, you should definitely check out Wisconsin for your next trip. Some of the most popular accommodations in the state are the Wisconsin Dells luxury cabins with indoor pools, but these other properties are just as worthy! Consider staying in one of these top vacation rentals with private pools in Wisconsin, USA, to elevate your vacation experience.
Frequently asked questions about vacation rentals in Wisconsin with a private pool
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