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Holiday rentals with a pool in Milwaukee

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Milwaukee

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

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Guest favourite
An inviting outdoor space showcases a wooden deck with two striped chairs positioned beside a large double door. A barbecue grill rests nearby, and a sign reading 'Hammer Hideaway' is mounted on the wall. Lush greenery and a clear sky provide a relaxed atmosphere.
Farm stay in Germantown
4.97 out of 5 average rating, 114 reviews

Lace & Woods Farm "Hammer Hideaway"

HEATED POOL MAY-SEPT FOR ADDITIONAL CHRG. Cozy designer custom built guest house nestled amongst a 10 acre hobby farm. come for a relaxing getaway. This home is an artistic gem! Boasting an open concept, with a queen bed on main level and twin mattress underneath , a full kitchen, cozy living area, wood burning fireplace. The loft has extra sleeping with a double bed and twin bed.Custom designed. Great location winter and summer, enjoy snowmobiling trails and skiing near by or beaches & hiking

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
4.98 out of 5 average rating, 236 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 Ridge 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.

Guest favourite
A spacious living area features a large sectional couch and a soft ottoman. A wooden table stands nearby, with a laptop resting on it. The kitchen area is visible, showcasing a bar with seating for four. Soft lighting enhances the neutral color palette.
Apartment in Lake Geneva
4.87 out of 5 average rating, 119 reviews

Lake Geneva relaxation!

4 mi to Downtown Lake Geneva, WI. Rent kayaks on Lake Como. New pool and tennis courts, amazing wildlife. Snowboard, cross country ski, sled on hills during our amazing Wisconsin winters. Dine at The Ridge restaurant CRAFTED or just buy a bottle of wine from the guest store and watch the sunset. Quiet corner of the condominium complex. Completely furnished. Beautiful comfortable King size bed, kitchen, cook and eat in! Balcony overlooking peaceful grounds. Private entry, laundry in building.

Superhost
An open living and dining area features a dark wooden dining table surrounded by black chairs. A light blue wall complements a cozy seating arrangement with armchairs and a sofa. Natural light enters through a large sliding door, with decorative elements and a chandelier enhancing the space.
Apartment in Lake Geneva
4.9 out of 5 average rating, 205 reviews

Lakeview at CasaComo

Mi Casa Como es su Casa Como Escape the daily grind and plan your getaway to our newly remodeled condo on Lake Como in Lake Geneva. We’re located just 5 minutes outside downtown Lake Geneva, so very convenient for shopping & dining, but peacefully located on quiet Lake Como. We have an outdoor community pool and tennis courts and just a few steps for The Ridge Hotel. We have all that you could want or need within walking distance, so keep your car parked. Come to Casa Como, stay & enjoy!

Guest favourite
The living area features a dark leather sofa adorned with blue throw pillows, accompanied by a light gray couch. A round woven pouf and an antique-style trunk serve as accent furniture. Large glass doors provide access to a balcony, with lake-themed decor on the wall.
Apartment in Lake Geneva
4.96 out of 5 average rating, 162 reviews

LakeView-SummerPool-FamilyFriendly-CloseToTown

Enjoy your stay at our family's Serene Lake condo with outdoor pool. NEWLY UPDATED Stylish and comfortable with amenities for any family to feel at home. Part of Interlaken community and set on Lake Como, we are surrounded by peaceful woods and often seen wild life, yet a quick drive into down town Lake Geneva, William's Bay and Fontana. Enjoy golfing, dining, water sports and all the region has to offer, then cozy up and relax with a view. NO RV, BOAT or TRAILER parking is allowed.

Guest favourite
A cozy living room features a light-colored sectional sofa complemented by colorful throw pillows. A plush, vibrant area rug adds warmth to the space. Two windows with light-filtering shades allow natural light, while a recliner and wooden table provide additional seating and surface space.
Home in Riverwest
4.89 out of 5 average rating, 18 reviews

Big BLUE Skyline VIEW

This bright and roomy 2 bedroom unit is the lower level of a 1900 Victorian duplex in the heart of Milwaukee was renovated 3 years ago. Situated on the edge of downtown, overlooking the river and downtown skyline you’ll have easy walking access to all the best neighborhoods. With 9 foot ceilings and a big fenced in yard with basketball hoop and patio furniture you'll be very comfortable staying with us. We are not a corporation, just a nice couple sharing our place. FREE PARKING too

Top guest favourite
The spacious living room features a large sectional sofa in neutral tones, focused around a gas fireplace. A flat-screen smart TV is mounted above the brick hearth. Sliding glass doors open to the outdoor patio, allowing natural light to fill the space.
Apartment in Lake Geneva
4.98 out of 5 average rating, 166 reviews

Quaint Lake Geneva Condo | Fireplace | WiFi

Discover Blue Lakes Escape, a newly-redecorated condo, steps away from Lake Como. Relax in the spacious great room with a smart TV, fireplace, desk area & access to quaint patio. Sit outside with a coffee, a good book, or a delicious BBQ. Enjoy free access to the shared amenities, including an outdoor pool, sports courts, & walking trails. Lake Como – 6 min walk Lodge Geneva National – 6 min walk Downtown – 8 min drive Book For Lasting Memories In Lake Geneva—See Details Below!

Guest favourite
An indoor pool area is showcased, featuring a large, clear pool with a projector screen positioned above. Natural stone walls and wood beams enhance the space, complemented by soft lighting. Large windows allow natural light to brighten the inviting environment.
Home in Sussex
4.89 out of 5 average rating, 123 reviews

Wooded Hills/Indoor Pool/Hot Tub/Arcade

Discover the allure of our 5BR Wisconsin retreat, where spacious elegance meets comfort. Enjoy a gourmet kitchen, a grand living room, and a game room with free arcade play. Dive into relaxation with our private, heated indoor pool. Outdoors, the terraced patio and fire pit invite memorable moments. Minutes from Milwaukee, our home is an idyllic base for both peaceful relaxation and lively exploration. Perfect for family or corporate escapes, it's a stay you'll cherish.

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
4.97 out of 5 average rating, 213 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!

Superhost
Flat in West Allis
4.79 out of 5 average rating, 19 reviews

Modern Apartment/ 8mins Downtown/ Parking/Pool/Gym

✨ Modern & Cozy Stay in the Heart of West Allis ✨ Stylish, light-filled apartment just steps away from the State Fair Grounds! Enjoy a cozy living room, fully equipped kitchen, peaceful bedroom, and access to a pool & lounge areas. Perfectly located near dining, shopping, and entertainment — right in the heart of West Allis, only steps away from the State Fair Grounds. 10 mins to Downtown Milwaukee 7 mins away to American Family Field

Top guest favourite
A decorative wall sign displays the word 'WELCOME' prominently. Beneath it, a white vase filled with yellow flowers adds a touch of color, set against a soft green wall, creating a friendly and inviting ambiance.
Home in Lake Geneva
4.93 out of 5 average rating, 163 reviews

Home away from Home

Our cozy and inviting home is designed for relaxation and fun, offering a wide range of amenities to make your stay unforgettable. Enjoy a refreshing dip in the in-ground pool, cozy up by the fireplace, or challenge your friends and family in the game room. just a short walk from the downtown area with shops, restaurants, and attraction all while enjoying the peace and comfort of a relaxing retreat. We look forward to hosting you!

Top guest favourite
Apartment in Lake Geneva
4.96 out of 5 average rating, 114 reviews

The Landis, in charming Lake Geneva

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 Ridge. 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.

Popular amenities for Milwaukee rentals with a pool

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Quick stats about holiday rentals with a pool in Milwaukee

  • Total holiday rentals

    Explore 40 holiday rentals in Milwaukee

  • Nightly prices starting at

    Milwaukee holiday rentals start at £8 per night before taxes and fees

  • Verified guest reviews

    Over 640 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Milwaukee holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Milwaukee rentals

  • Nearby attractions

    Milwaukee’s top spots include Milwaukee County Zoo, Harley-Davidson Museum and Milwaukee Art Museum

Destinations to explore