Holiday rentals with a pool in Milwaukee

Vacation home: heated inground pool on 4+ acres

TIMELESS CHARM MEETS MODERN ELEGANCE **MAY SPECIAL GUARANTEED 80 degrees pool temp no extra cost thru 5/22 Where the charm of classic aesthetics seamlessly intertwines with the conveniences of contemporary living. 4 acre + estate with plenty of room for outdoor activities such as swimming, water basketball & volleyball, outdoor basketball, sunbathing, barbecues or picnics. This vacation retreat is only minutes away from Lake Michigan, movie theaters, restaurants, golf courses, coffee shops.

Close to Lake with Great Ammenities & Breakfast!

I want you to be able to do things here that you can't do in a hotel. If you're grillilng out, having a bonfire or watching movies all night long, you can turn up that volumn as loud as you want all night long! I posted my listing under "entire home" as you do get so much more than just renting "a room". When I have guests I stay in my office or bedroom so my guests feel more comfortable utalizing entire home & yard. In fact, if you don't ask for breakfast, you may not even see me at all.

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.

Brewers Hill Gem w/hot tub & seasonal shared pool

Your family will be close to everything when you stay at this centrally-located place. Walking distance to Brady Street, the Milwaukee River Walk, shops, restaurants and coffee houses. Less than a mile from Fiserv Forum, downtown Milwaukee and just minutes from Bradford Beach. This pet friendly unit has a private fenced in yard, BBQ grill, off street parking for your vehicles and motorcycles, and a hot tub for your use.

North End 519

This special place is close to everything, making it easy to plan your visit. North End is a lively property where we offer fully furnished studios, stocked with everything you need to feel at home. North End is in a community that includes a Fitness Center, Lounge, and Covered Parking - Fee may apply. North End is a Walker's Paradise with a Walk Score of 92, a Transit Score of 67, and a Bike Score of 83.

Beautiful Downtown 2 Bedroom 2 Bathroom Apartment

Take it easy at this unique and tranquil getaway. This is a Beautiful cozy two bedroom two bedroom unit. That offer a peaceful relax environment, with a view of Downtown. There's balcony, a gym, pool and game run available for your convenience. You will be in walking distance. From the Fiserv Forum (Bucks Arena), grocery stores, restaurants and night life. You're going to Love your stay here.... 😊

The Peacock Place w/ Shared Seasonal Outdoor Pool

This 3 bedroom, 1 bath, open concept lower unit of a duplex is located in Brewer's Hill. This unit has tons of natural light, original hard wood floors, pocket doors and claw foot soaking tub. This pet friendly unit has off street parking for 2 vehicles or motorcycles, and a private yard with patio and BBQ grill for your use. Walking distance to Brady Street, downtown and Fiserv Forum.

2 Story - 2Br Condo

Forget your worries in this spacious and serene space. 2 story townhouse story 2 Bedroom 1.5 bathroom condo with a patio and pool and courtyard for a simple stay. Perfect for in town family visits or quick work stays. The pool is open in the summer months which should be upcoming. Smoking area outside on patio or in vestibule. NO SMOKING IN HOUSE

Charming 1BR Apt with Balcony+Pool+Gym

Enjoy luxury living in this brand new building on Milwaukee's East Side. The building is fully loaded with amenities so you can live, work, and play all under one roof. And when you're ready to venture out, the central location provides quick access to Fiserv Forum, Lake Michigan, Brady St, and more.

Townhome Villa private oasis

Forget your worries in this spacious and serene space.

Luxury Mequon 2x2 Apartment

Enjoy your stay in the Milwaukee suburbs