Holiday rentals with a pool in Wisconsin

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Wisconsin

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

A spiral staircase provides access to the lofted area, featuring a seating arrangement with a wicker chair. The main level includes a well-equipped kitchen area with a sleek countertop and modern fixtures, framed by rustic wooden beams and a welcoming entry door.

Home in Danbury

Tall Moon Cabin

Welcome to Tall Moon Timber House! Our beautiful 2-level cabin is located in Danbury, Wisconsin. Relax in our 4 bed, 1 bath cabin nestled within Voyager Village. This gives our guests access to the golf course, beaches, indoor swimming pool*, bocce ball, tennis and pickle ball courts, basketball courts, and other recreational activities! All of this and just 2 hours outside the Twin Cities. Please see the amenities section below for a full list. *Closed in early January for annual maintenance

4.86 out of 5 average rating, 112 reviews

Top guest favourite

A manicured lawn gently slopes towards a serene body of water in the distance, framed by tall trees on either side. The landscape features lush greenery under a partly cloudy sky, creating an open and inviting outdoor space.

Apartment in Lake Geneva

Lake Geneva Cloud 9

A resort community with outdoor pool (open during the summer season only) boat launch, tennis courts and small craft rentals on the premises. Beautiful views of Lake Como from the patio. Five minute drive to Downtown Lake Geneva. Free parking and keypad entry. Walk to The Lodge Hotel Resort and enjoy the use of their amenities for a small user fee which includes indoor and outdoor pools, spa, whirlpool, fitness center and restaurant. The condo is comfy and ready to make your stay memorable.

4.98 out of 5 average rating, 259 reviews

Superhost

A spacious deck offers a relaxing outdoor seating area with four chairs and a table, set against the backdrop of the Mississippi River and rolling hills. The sky is filled with clouds, reflecting various shades as the sun sets over the water.

Cabin in Lynxville

River Run Ridge - HOT TUB- river view - sleeps 16

Come enjoy the breathtaking views all around the living and dining area of this beautiful home located in Lynxville. This upgraded home with 5 bedrooms and 3 baths, can accommodate up to 14 people . Spacious dining/living area for family gatherings, bonus projector room in lower level and large deck to sit and enjoy the view of the Mississippi, be it day or night while grilling out in a summer night. Fully stocked for your getaway. Close proximity to many local attractions and boat ramp.

4.88 out of 5 average rating, 144 reviews

Top guest favourite

A log cabin-style home features a wide front deck with sturdy railings, complemented by large windows that allow natural light to flood the interior. A stone chimney and well-maintained landscaping add to the inviting exterior.

Cabin in Nekoosa

Brown Bear Lodge @ Lake Arrowhead Sand Valley GOLF

Minutes to Sand Valley & located in prestigious Lake Arrowhead! Play 4 championship golf courses, then unwind at Brown Bear Lodge—a cozy Northwoods retreat perfect for golf groups, families & friends. Enjoy a pool table, wet bar, stone fireplace, spacious gathering areas, firepit, fast Wi-Fi, fully equipped kitchen & comfortable beds. Lake Arrowhead offers private lakes, beaches, 2 seasonal pools, trails, pickleball, dining & endless year-round recreation. Book your unforgettable getaway!

4.91 out of 5 average rating, 149 reviews

Top guest favourite

The living area showcases a spacious layout with a leather pullout couch and armchair, complemented by a modern coffee table. A smart TV is mounted on one wall, while an electric fireplace adds warmth. The kitchen features a bar with three stools, enhancing the inviting atmosphere.

Apartment in Wisconsin Dells

The Wanderlust at the Sunset Cove

Riverfront one bedroom condo in a tranquil area of Downtown Wisconsin Dells. Take a stroll near the beautiful River Walk and enjoy the magnificent scenery and unique attractions of Downtown Wisconsin Dells. Whether you need a few days to relax and decompress or if you are in town for business or games, our condo offers a fully equipped kitchen, a king size bed and a queen size pull out couch . There is an indoor community pool, hot tub and sauna. There is also a seasonal outdoor pool .

4.97 out of 5 average rating, 214 reviews

Guest favourite

A spacious living area features comfortable gray sectional sofas adorned with turquoise cushions. A light wooden coffee table is centered on a soft area rug. Soft lighting is provided by table lamps, and large sliding doors lead to an outdoor space with a view of greenery.

Home in Lake Geneva

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

✔ 1000 Sq. Ft. Ground Level Condo ✔ Patio overlooking expansive lawn ✔ Resort-like community ✔ New community pool ✔ Tennis,v-ball Courts ✔K-cup & drip coffee, Big Screen TV, Cable, FAST wifi ✔Steps to the Ridge Hotel w/ restaurant, coffee/wine shop ✔ Direct lake access w/boat launch, kayak, SUP board rental ✔ 5 min drive to Shops and dining in DT Lake Geneva ✔ Fully equipped kitchen ✔ Close to summer fun: Lake, golf, zipline, hiking ✔Close to Winter fun: Ice Castle, skiing, snowshoeing

4.95 out of 5 average rating, 122 reviews

Superhost

Apartment in Wisconsin Dells

Luxurious Chula Vista Retreat

No resort fees! Experience all the Wisconsin Dells has to offer while staying in this luxurious condo, located inside the action-packed Chula Vista Resort! Enjoy the resort's restaurants, 18-hole golf course, zip line and so much more! Minutes from all of the area's attractions including Mt. Olympus, Noah's Ark and hiking trails! Then relax in our Jacuzzi tub, cozy up to our two fireplaces, hang out in our spacious living room or cook a family meal in our full-size kitchen!

4.76 out of 5 average rating, 144 reviews

Superhost

An indoor pool with clear blue water is featured, surrounded by smooth concrete flooring. Bright overhead lights illuminate the space, while large glass doors offer views of the outdoor landscape. Greenery decorates the walls, adding a touch of nature to the area.

Home in Allouez

Amazing Six Bedroom Green Bay Vacation Home!!

Amazing one-of-a-kind home is built for entertaining and full of amenities. You'll love the huge indoor pool that is heated year-round! Very spacious layout. Home has hosted celebrities & Packers Hall of Fame Players. Amenities include a full arcade, outdoor sauna, theatre room, large open kitchen and living room, high-end massage chair, poker table, and more! Six-minute drive to Lambeau, five-minute drive to the airport, very close to everything. 5,200 Sq Feet

4.86 out of 5 average rating, 271 reviews

Top guest favourite

Apartment in Lake Geneva

Elegant condo w/ fireplace & balcony, king bed

Kick back and relax in this calm, elegant one bedroom Villa with a KING size bed. This vacation rental is in a quiet area of Lake Geneva, but just minutes from all the vibrancy of downtown Lake Geneva or Williams Bay. It is within walking distance to Mars Resort, The Getaway or The Lodge Geneva National. This is a perfect spot for couples looking for a relaxing getaway. Local laws require all guests names and address be provided prior to check in.

4.97 out of 5 average rating, 157 reviews

Top guest favourite

A cozy living area features a dark sofa set against a textured wall, with a small decorative pillow. An open kitchen bar with four modern black stools invites gatherings, while greenery enhances the room's decor. Natural light is filtered through large windows.

Apartment in Lake Geneva

Relaxing Villa with Amazing Amenities!

Resort day passes included with booking! Hot tub, indoor and outdoor pool, outdoor bar and fire pit, sauna, the list goes on! Only five minutes from downtown Lake Geneva, this second floor condo offers the best of both worlds. Enjoy the laid back Lake Como attractions, or have a blast in Lake Geneva! This hidden gem is perfect from golfers (only 5 minutes from Geneva National) to families. Give us a try, and enjoy a discount on your second stay!

4.97 out of 5 average rating, 237 reviews

Top guest favourite

A serene outdoor setting features a stone fire pit surrounded by wooden benches. The custom-built home, with large windows, is visible in the background. Soft twilight hues illuminate the peaceful landscape, complemented by trees lining the property.

Earthen home in Elkhart Lake

Secluded Elkhart Retreat | Pool, Hot Tub & Sunset

Nestled just minutes from Downtown Elkhart Lake, this custom-built cordwood home offers a secluded sanctuary experience. Perched atop a hill, the unique 16-sided house provides breathtaking views of the state forest and surrounding farmland. Despite its remote feel, you’re only a 5-minute drive from the charming Elkhart Lake business district. Day hikes on the ice age trail are just steps away from the home. Tap the ❤️ to save this listing!

4.98 out of 5 average rating, 162 reviews

Superhost

A unique A-frame exterior features a mix of black wooden siding and natural brown shingles. A small patio area is visible with a round table and four black chairs, surrounded by well-kept shrubs and landscaped gravel.

Apartment in Wisconsin Dells

Dells Retreat-A Romantic Haven-Jacuzzi,Pool&HotTub

Upgrade to the Noah's Ark & Land Of NATURA Waterpark Packages after booking! See below for details. Welcome to Dells Retreat, your ultimate vacation destination in the heart of Wisconsin Dells Nestled in the picturesque Tamarack Resort, our property offers a serene and scenic setting for your vacation. With endless amenities and attractions just minutes away from the downtown and Lake Delton. A perfect escape for travelers of all ages.

4.9 out of 5 average rating, 136 reviews