
Holiday rentals with a pool in Milwaukee County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Milwaukee County
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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.

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.

Beautiful 6 bedroom with Heated Pool & Jacuzzi
Relax with the whole family at this peaceful place to stay right in the middle of beautiful Whitnall Park. You won't find a more peaceful view of the woods and park. Our beautiful home has a large heated pool with brand new 6 person jacuzzi. Brand new Kitchen and updated bathrooms. Master suite is very romantic with steam shower, jacuzzi tub, and luxury bed and fireplace. Family Friendly OR Romantic Getaway!

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.... ๐

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.
Popular amenities for Milwaukee County rentals with a pool
House rentals with a pool

Townhome Villa private oasis

Brewers Hill Gem w/hot tub & seasonal shared pool

Close to Lake with Great Ammenities & Breakfast!

The Peacock Place w/ Shared Seasonal Outdoor Pool
Other holiday rentals with a pool

North End 519

Brewers Hill Gem w/hot tub & seasonal shared pool

Charming 1BR Apt with Balcony+Pool+Gym

2 Story - 2Br Condo

Close to Lake with Great Ammenities & Breakfast!

The Peacock Place w/ Shared Seasonal Outdoor Pool

Townhome Villa private oasis

Beautiful Downtown 2 Bedroom 2 Bathroom Apartment
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- Alpine Valley Resort
- Kohler-Andrae State Park
- Wilmot Mountain Ski Resort
- Erin Hills Golf Course
- Illinois Beach State Park
- Milwaukee County Zoo
- Milwaukee Public Museum
- Baird Center
- Bradford Beach
- Sunburst
- Discovery World
- Riverside Theater
- Blackwolf Run Golf Course
- Marquette University
- American Family Field
- Fiserv Forum
- Lake Park
- Holy Hill National Shrine of Mary
- Little Switzerland Ski Area
- South Shore Park
- Betty Brinn Children's Museum
- Kettle Moraine State Forest - Northern Unit
- Mitchell Park Horticultural Conservatory
- American Family Insurance Amphitheater




