18 Best Vacation Rentals With Private Pool In Wisconsin - Updated 2022

Andrea Mae
Andrea Mae 
Updated

Wisconsin, known for its delicious cheese and historical places, is a great place to visit. If you are up for some scenic trips, you might want to visit Devil’s Lake State Park to witness some magnificent water views or check out the other lakes and places for snowboarding in the state. You can even explore some engaging outdoor activities such as hiking and rock climbing. 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 a private pool in Wisconsin.

1. Luxury villa with a hot tub and pool (from USD 599)

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 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.

PEACEFUL RELAXING LUXURY VILLA IN-SIDE POOL & HOT TUB *Krakow* SHAWANO LAKE-12mi
5 reviews  Wifi Available
House 10 Guests 4 Bedrooms 5 Bathrooms

Accommodates: 10
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
the beds were very comfortable
quiet secluded getaway with comfortable beds and linens with a perfect pool and hot tub
Cleanliness:
it was clean welcoming and spacious
Host:
ava was quick to respond to our concerns and seemed very kind
Read more reviews

2. Spacious home with an indoor pool (from USD 1139)

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, 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.

Cerca de la casa de cinco dormitorios Lambeau con piscina cubierta
42 reviews  Wifi Available
House 14 Guests 6 Bedrooms 4 Bathrooms

Accommodates: 14
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
we enjoyed the large heated pool fun arcade games and appreciated the tea/coffee station
the pool was super warm and there were various water toys and floaties
huge living room for gatherings and games
the beds were extremely comfortable and the family area was spacious enough for everyone
the kitchen allowed for family cooking and the area also includes a good selection of deliver-in options
Cleanliness:
home was very clean and had sanitizing and cleaning supplies available
the pool is awesome: clean not heavily chlorinated lots of fun toys
rooms are on all 3 floors and were clean with ample linens
home was clean has open floor plan and lots of sunlight
Host:
we all had a great time thanks tom for hosting us
Read more reviews

3. Cozy getaway with a pool near Whitewater and Rice Lakes (from USD 750)

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.

¡Tan amplias y acogedoras! Cerca del lago con un patio privado con piscina
16 reviews  Wifi Available
House 6 Guests 7 Bedrooms 4 Bathrooms

Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the master bedroom lights had to be on in order to use the ceiling fan
there was plenty of family space and the kitchen was great
Cleanliness:
very clean and private
the house was roomy clean and comfortable and the grounds were really nice
Host:
the owner was great she response to any question or concenrs very quickly
it was a peaceful friendly stay
Location:
great house for couples with a under 1 minute walk to rice lake
Read more reviews

4. Lakefront holiday home in Newton best for families (from USD 4500)

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 swimming pool that overlooks the waters of Wisconsin. 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.

Inmaculada casa de Wisconsin en el hermoso lago Michigan
16 reviews  Wifi Available
House 16 Guests 9 Bedrooms 6 Bathrooms

Accommodates: 16
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the pool was great for the kids heated
Host:
the owners were warm friendly and made sure that we had an exceptional time
the property managers were extremely kind and helpful
Read more reviews

5. Pet-friendly home with lake views in Twin Lakes (from USD 1025)

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 pool. 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.

Increíble casa del lago con piscina climatizada en el suelo ~ terrenos arbolados privados
45 reviews  Wifi Available
estate 24 Guests 8 Bedrooms 4 Bathrooms

Accommodates: 24
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
everyone loved using the heated pool
Cleanliness:
we had been promised an extremely clean house with covid concerns and we did not get that
Host:
the property owner was helpful and quickly answered any questions we had
Read more reviews

6. Lakeview getaway with outdoor decks in Lake Geneva (from USD 900)

The whole family can soak in the marvelous view Lake Geneva has to offer because this vacation rental is only a 2.8-mile (4.5-kilometer) drive from downtown. At this Airbnb with an indoor pool in Wisconsin, you can fully enjoy the tranquillity of nature with its 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.

Lodge Home on 3 Acres | 2.8 Miles to Town | Views
Lake Geneva, Wisconsin, United States
19 reviews  Wifi Available
Entire home 5 Beds 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Cleanliness:
lots of nice touches clean place
Location:
a bit rigid but a nice place
Read more reviews

7. Well-furnished retreat with nature views in Ripon (from USD 1500)

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.

Piscina cubierta, junto al lago
20 reviews  Wifi Available
House 16 Guests 6 Bedrooms 4 Bathrooms

Accommodates: 16
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Cleanliness:
bright clean plenty of room for groups
Host:
owners were great hosts
the hosts were fast and helpful and also very accommodating to our unique needs/ requests
the owners went above and beyond to make our stay as comfortable as possible
the owners were very responsive and helpful to make the weekend as enjoyable as possible for us
jennifer and kevin were great hosts
Read more reviews

8. Luxurious family home with hot tub in Burke (from USD 262)

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.

Barbacoa de lujo / fiesta en la piscina / vacaciones / destino de luna de miel
53 reviews  Wifi Available
House 10 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 10
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
we loved the pool and hot tub the deck was perfect for dinner snacks and drinking
we truly enjoyed the spacious deck area swimming pool and hot tub
with pool cabana and hot tub; it was a relaxation retreat we needed
the kitchen is well furnished and the hot tub was amazing
Cleanliness:
clean and communication was excellent
comfortable beds beautiful gazebo very clean and reasonable
the house was very clean and great communication with the owner
house was clean with good amenities
we so enjoyed gathering is this beautiful space the kitchen was well stocked and clean as well as eco-friendly
Host:
the hosts were friendly and responsive
it was a great comfort that our hosts were very attentive to our questions and needs
Location:
plus great location (secluded but only a few minutes away from downtown)
great place for our getaway close to everything
Read more reviews

9. Family-friendly luxury home with hot tub in Hudson (from USD 1667)

In the middle of Hudson, Wisconsin, is where you’ll find this spacious home that features an outdoor 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 own feast at the contemporary kitchen or the outdoor grill. Some unique amenities at the property are the trampoline, wiffle ball field, the playground, and the hammocks. The place is ideal for family vacations since there are plenty of recreational facilities for the little ones to enjoy.

Retiro recreativo grande
11 reviews  Wifi Available
House 30 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 30
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the backyard was a dream set up for fun with a pool hot tub and yard games
kitchen dining room large and nice living roomthe pool hot tub and outside patio very nice
plenty of space and activities for adults plus 10 little kids to swim and play outside
Cleanliness:
the house itself was very clean and more than accommodated our group of 10
Host:
jason was a great host prior to check-in he was responsive to questions and easy to communicate with
the owner communicates well and ensures you have a good stay
jason was very accommodating starting with check-in jason was very flexible and gave us a full tour upon arrival
Read more reviews

10. Spacious getaway with hot tub in Madison (from USD 925)

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. 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.

Perfecto para grupos grandes y familias ~ 7. 1 millas de UW Madison
51 reviews  Wifi Available
House 15 Guests 5 Bedrooms 3 Bathrooms

Accommodates: 15
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
the pool is amazing (and doesn't have the harsh chlorine - huge bonus)
Cleanliness:
we didn’t use the pool but it looked clean and fun
the house is very clean and spacious
the house is beautiful clean spacious and everything we had hoped for
the pool and hot tub were very clean and well heated
Host:
the owners are lovely and walked us through everything
this home had everything owners were wonderful and property was spotless
julie the host is very nice and extremely responsive
hosts were great and the home was clean and had pretty much anything you would need
owners were great and the home was clean and organized
Location:
walking distance to a great park
nice home good communication and very close to epic
great property great hosts we really enjoyed our time here the pool was great and the location convenient to everything
everything in place for a perfect family stay
Read more reviews

11. Pet-friendly sanctuary with lake views in Markesan (from USD 725)

This area is located near Puckaway Lake, which you can explore by renting a boat. The cabin in Wisconsin with an indoor pool has a maximum capacity of twelve guests with its six large bedrooms. The whole pack can soak in the house pool and hot tub.

You can also have a good time with the custom-made bar and play with the slot machine and pinball machine. A few minutes of driving can take you to shopping malls, restaurants, and grocery stores.

Adeline's House of Cool
41 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
Cleanliness:
there are 6 bedrooms and all very clean and comfortable
Read more reviews

12. Exclusive property with hot tub and heated pool in Caledonia (from USD 200)

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 definitely enjoy your stay here. An outdoor pool is also available should you want a relaxing dip. It has an entertainment area with a 110-inch (279.4-centimeter) widescreen and a projector for movie marathons.

"The Retreat" 7 1/2 acres de propiedad privada
129 reviews  Wifi Available
House 20 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 20
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
large well taken care of yard and nice pool and hot tub
the game room/garage was perfect
Cleanliness:
easy check-in everything clean and great location just off the i-94 exit
large great room clean kitchen and sleeping spaces when we finally went inside
Host:
the owner is very easy to work with as well
robert was the most gracious host we’ve had yet
robert was so helpful and easy to communicate with before and during our stay
Location:
i highly recommend this location
"the retreat was an outstanding place for a five day trip to wisconsin
Read more reviews

13. Secluded paradise with a hot tub in Somerset (from USD 785)

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.

Resort LeMire
Somerset, Wisconsin, United States
171 reviews Superhost  Wifi Available
Entire home 7 Beds 10 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
(by the way the wifi is excellent
great amenities incredible kitchen and plenty of space
the gator jeep hot tub pool and steam shower are the best
the pool hot tub in-ground trampoline fire pit etc were in perfect condition
the pool and hot tub are amazing
Cleanliness:
it was sparking clean and well equipped
very clean and beautiful perfect spot for any event
extremely clean and comfortable and the property was amazing
the place was clean spacious and welcoming
the house is very clean and has so much to do
Host:
kelly was a wonderful host
kelly is a wonderful host
kelly is a fabulous host
kelly is a great host
kelly was super responsive to questions we had
Location:
such an amazing break from reality lovely place
our family wanted a place to get away and this was the perfect spot
it 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 cities
a perfect place for a family get together
Read more reviews

14. Luxurious house with heated pool in Milwaukee (from USD 1129)

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. 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.

Unique House with Indoor Heated Pool & Sauna
Milwaukee, Wisconsin, United States
48 reviews Superhost  Wifi Available
Entire home 5 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
Cleanliness:
the house was clean sanitized and quiet
Host:
the hosts were fast and helpful and also very accommodating to our unique needs/ requests
thanks for hosting our family
Location:
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

15. Newly renovated home in Hager City best for families (from USD 693)

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.

Spectacular views + acreage + Mississippi + pool
Hager City, Wisconsin, United States
29 reviews  Wifi Available
Entire home 3 Beds 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
the top appliance kitchen was a dream come true for my chef-like husband
the natural light flowing through every room was inspiring
i loved sitting in all the different rooms and taking in the views
the house is decorated beautifully and spacious the beds are comfortable and the views are spectacular
furniture is so comfortable beds are cozy and showers and tubs are amazing
Cleanliness:
beautiful clean and well stocked home
the pool was heated and clean and overlooking the river
Host:
stunning comfortable and host was available and responsive
book while you can because this was one of a kind
Location:
the neighborhood is quiet and quaint and perfect for a little getaway
Read more reviews

16. Cul-de-sac poolside serenity in Appleton

A nice-sized vacation home rental that is ideal for 10 people is this four-bedroom property in Appleton. This holiday home is tucked at the end of a cul-de-sac, so you can expect complete privacy and peace during your stay. The exterior displays a typical suburban American home with a spacious driveway. The outdoor in-ground pool with a slide is surrounded by a tree-lined field. To make your stay even better, there’s a large hot tub that can fit seven people altogether.

July 4th and EAA Poolside Serenity
1 review
House 10 Guests 4 Bedrooms 4 Bathrooms
Top guest reviews
Amenities & Room:
worked well for my family pool gave entertainment for those not wanting to venture out
Read more reviews

17. Cozy country home in Montello perfect for reunions

This seven-bedroom country home in Montello, Wisconsin, could be the venue for your next company outing or family reunion. The rental is in a large campsite, which guests are welcome to use for their outdoor activities. Typically, this house can sleep around 25 people, but the owners allow even bigger groups that can bring campers and RVs, which would be parked on the campgrounds. The place is also pet-friendly, so if you’re half-hearted about leaving your furry friends behind, now you don’t have to be!

4,000 sq. ft. Cozy 3 Story Country Home; Perfect for Reunions, Camping, and More
17 reviews
estate 99 Guests 7 Bedrooms 4 Bathrooms
Top guest reviews
Amenities & Room:
icing space is wonderful great furniture and tables
the pool and patio area was perfect for entertaining
the pool was great but would have been better if it wasn't cloudy
Cleanliness:
the water was clean and warm
Host:
owners were absolutely wonderful
thank you to the owners for having us
the hosts were responsive and very accommodating
the owners were easy to contact & great to work with
amazing great time and great owners will be hoping to go back again jerry was awesome thank you guys
Read more reviews

18. 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.

1/2 Mile to Downtown Elkhart Lake-Beautiful 25 acres of pristine country living
Plymouth, WI, US
10 Guests 4 Bedrooms 2 Bathrooms

Have a great 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 Wisconsin vacation rentals with a private pool

1. Which Wisconsin vacation rentals with a private pool have rooms with great views?

This immaculate Wisconsin lake home, this stellar home with magnificent lake views, and this marvelous cabin-like home with indoor pool are some of the vacation rentals with a private pool in Wisconsin that also have rooms with great views.

2. Which Wisconsin vacation rentals with a private pool are good for families?

This lovely home in a tranquil setting, this spacious recreational retreat, and this cozy country home perfect for reunions are the properties you should look at if you’re on the hunt for a vacation rental with a private pool in Wisconsin that is suitable for families.

3. Which Wisconsin vacation rentals with a private pool are good for kids?

Those who are coming not only with their adult loved ones but also with children, here are the vacation rentals in Wisconsin that are good for kids: spacious getaway with an outdoor pool, secluded paradise with a hot tub, and immaculate Wisconsin lake home.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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I am a freelance content writer who resides in the Philippines. I am a teacher by profession and a writer at heart. I have traveled several times locally with my family and sometimes with friends....Read more

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