Vacation 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 favorite

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

4.85 out of 5 average rating, 109 reviews

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

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Top guest favorite

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.

Condo in Lake Geneva

4.98 out of 5 average rating, 254 reviews

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.

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Guest favorite

A quaint blue house is shown from the side, surrounded by lush green grass. A wooden fence partially outlines the property, with a few flowering plants positioned along the edge. Clear skies and sunlight illuminate the exterior, highlighting its welcoming presence.

Home in Prairie du Chien

4.98 out of 5 average rating, 172 reviews

Ohio Street Retreat- hot tub, massage chair, pool

After a fun day in The Driftless Area, come relax and unwind in Prairie du Chien. Beautifully decorated 2 bedroom home with a spacious kitchen, large island, dishwasher, washer/dryer & 5' walk in shower. We supply all cooking/baking items/utensils. High-speed internet with smart TVs in both bedrooms and living room. Outdoor pool (seasonal), hot tub and massage chair. We love dogs too, so we provide a dog run (there is a pet fee). For our fishermen- there is off street parking for your boats.

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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

4.91 out of 5 average rating, 139 reviews

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.

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Top guest favorite

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

4.9 out of 5 average rating, 143 reviews

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!

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Top guest favorite

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.

Condo in Wisconsin Dells

4.98 out of 5 average rating, 210 reviews

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 .

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Superhost

Condo in Wisconsin Dells

4.76 out of 5 average rating, 139 reviews

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!

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Top guest favorite

Cabin in Lodi

4.98 out of 5 average rating, 64 reviews

Private Resort Cabin | Pool • Hot Tub • Sauna

Escape to your own private resort in the Wisconsin countryside. Set on 8.43 peaceful acres, Wanderlust Cabin brings together the warmth of a true log home with everything you need for an unforgettable getaway—private heated pool, 8-person hot tub, outdoor sauna, firepit, fireplace and beautiful spaces to gather. Secluded enough to truly unwind, yet just minutes from Lake Wisconsin, hiking trails and downtown Lodi, with skiing, wineries, dining and plenty to explore nearby.

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Guest favorite

An indoor space features a pool surrounded by comfortable seating arrangements, with soft lighting enhancing the atmosphere. A digital fireplace display is mounted against the wall, and the fully-equipped kitchen area is visible in the background.

Cabin in Maiden Rock

4.95 out of 5 average rating, 58 reviews

Lake Pepin Cabin | Indoor Pool w/ Theater & Arcade

Welcome to The River Pools Cabin one of a kind retreat near beautiful Lake Pepin, where unforgettable memories await. Sleeping up to 16 guests, this unique smart home features a private indoor pool, hot tub, theater style 16-foot TV screen, arcade games, gaming console, outdoor kitchen, fire pit, and much more. Perfect for families, friends, reunions, and Twin Cities getaways. A rental agreement will be sent for electronic signature after booking.

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Top guest favorite

Condo in Lake Geneva

4.97 out of 5 average rating, 153 reviews

The Landis, spacious condo w/ pool & 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.

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Top guest favorite

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.

Condo in Lake Geneva

4.97 out of 5 average rating, 234 reviews

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!

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Guest favorite

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.

Condo in Wisconsin Dells

4.9 out of 5 average rating, 131 reviews

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.

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