Apartment
10.0(67 Reviews)
1 Bedroom
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $153/Night
7 Nights - US $1,073
Milwaukee Holiday Rentals
We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.
- Up-front pricing
- No markup
- Trusted partners
Compare Villas, Resorts, & Rentals in Milwaukee
10.0
Apartment
10.0(10 Reviews)
2 Bedrooms
4 Guests
- Air Conditioner
Internet
Child Friendly
Wheelchair Accessible
US $276/Night
7 Nights - US $1,932
House
10.0(7 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $210/Night
7 Nights - US $1,470
Villa
10.0(45 Reviews)
2 Bedrooms
8 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $415/Night
7 Nights - US $2,908
House
10.0(5 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $264/Night
7 Nights - US $1,851
House
10.0(38 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $422/Night
7 Nights - US $2,955
House
10.0(35 Reviews)
2 Bedrooms
6 Guests
Breakfast- Parking
Ocean View- Balcony/Terrace
US $338/Night
7 Nights - US $2,363
Villa
10.0(32 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $334/Night
7 Nights - US $2,336
Apartment
10.0(31 Reviews)
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $176/Night
7 Nights - US $1,230
Luxury Holiday Rentals in Milwaukee
Over 3070+ Luxury Holiday Rentals in or Near Milwaukee
Unlock the Best Price
Apartment
9.6(20 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $6,674/Night
7 Nights - US $46,720
House
10.0(13 Reviews)
5 Bedrooms
10 Guests
- Hot Tub
- Parking
Spa- Ocean View
US $4,032/Night
7 Nights - US $28,225
House
9.8(13 Reviews)
8 Bedrooms
15 Guests
Private Pool- Hot Tub
- Breakfast
- Parking
US $3,987/Night
7 Nights - US $27,912
House
10.0(13 Reviews)
6 Bedrooms
12 Guests
- Hot Tub
- Air Conditioner
- Internet
- Child Friendly
US $3,134/Night
7 Nights - US $21,936
Hotel
6.6(143 Reviews)
- Private Pool
- Hot Tub
- Breakfast
- Parking
US $3,000/Night
7 Nights - US $21,000
House
10.0(2 Reviews)
4 Bedrooms
8 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $2,615/Night
7 Nights - US $18,308
Other
9.8(25 Reviews)
6 Bedrooms
16 Guests
- Breakfast
- Parking
Pool- Balcony/Terrace
US $1,925/Night
7 Nights - US $13,474
House
1 Bedroom
18 Guests
- Private Pool
Private Beach
Oceanfront- Hot Tub
US $1,889/Night
7 Nights - US $13,224
Top-Rated Holiday Rentals with a Pool in Milwaukee
Over 401+ The Best Private Villas and Holiday Rentals in Milwaukee with a Pool
House
10.0(125 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $551/Night
7 Nights - US $3,855
Other
10.0(60 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $178/Night
7 Nights - US $1,247
Apartment
10.0(53 Reviews)
3 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $216/Night
7 Nights - US $1,514
Apartment
10.0(10 Reviews)
1 Bedroom
5 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $151/Night
7 Nights - US $1,054
House
10.0(9 Reviews)
3 Bedrooms
7 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $751/Night
7 Nights - US $5,256
House
10.0(4 Reviews)
4 Bedrooms
10 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $1,038/Night
7 Nights - US $7,263
House
10.0(2 Reviews)
6 Bedrooms
17 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,228/Night
7 Nights - US $8,599
Apartment
10.0(2 Reviews)
1 Bedroom
5 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $431/Night
7 Nights - US $3,020
Hotel
10.0(2 Reviews)
- Breakfast
- Parking
- Pool
- Kitchen
US $288/Night
7 Nights - US $2,018
Pet-Friendly Holiday Rentals in Milwaukee
Over 904+ Pet-Friendly Holiday Rentals in or Near Milwaukee
House
10.0(17 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
US $355/Night
7 Nights - US $2,483
Apartment
10.0(5 Reviews)
2 Bedrooms
8 Guests
- Private Beach
- Breakfast
- Parking
- Ocean View
US $255/Night
7 Nights - US $1,787
Cottage
2.0(1 Review)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $538/Night
7 Nights - US $3,767
House
10.0(11 Reviews)
1 Bedroom
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $375/Night
7 Nights - US $2,624
Apartment
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $288/Night
7 Nights - US $2,014
Villa
10.0(11 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $260/Night
7 Nights - US $1,823
House
10.0(10 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
US $226/Night
7 Nights - US $1,582
House
10.0(10 Reviews)
1 Bedroom
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $210/Night
7 Nights - US $1,473
House
10.0(10 Reviews)
1 Bedroom
3 Guests
- Kitchen
- Pet Friendly
- Child Friendly
- Laundry
US $137/Night
7 Nights - US $957
Large Holiday Rentals and Private Villas in Milwaukee
Over 441+ Large Holiday Rentals and Private Villas in or Near Milwaukee
Apartment
10.0(16 Reviews)
2 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $201/Night
7 Nights - US $1,410
House
10.0(2 Reviews)
3 Bedrooms
12 Guests
- Parking
- Internet
- Pet Friendly
Bar
US $474/Night
7 Nights - US $3,318
House
4 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Air Conditioner
US $540/Night
7 Nights - US $3,780
Apartment
10.0(1 Review)
1 Bedroom
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $385/Night
7 Nights - US $2,697
House
10.0(1 Review)
5 Bedrooms
12 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $257/Night
7 Nights - US $1,796
Apartment
9.8(10 Reviews)
2 Bedrooms
12 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $343/Night
7 Nights - US $2,402
Apartment
9.0(11 Reviews)
2 Bedrooms
12 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $394/Night
7 Nights - US $2,760
Condo
9.0(8 Reviews)
2 Bedrooms
16 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $656/Night
7 Nights - US $4,593
Condo
8.8(5 Reviews)
2 Bedrooms
16 Guests
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $491/Night
7 Nights - US $3,439
Wheelchair Accessible Holiday Homes in Milwaukee
Over 930+ Wheelchair Accessible Holiday Homes in or Near Milwaukee
Apartment
10.0(19 Reviews)
1 Bedroom
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $376/Night
7 Nights - US $2,633
Apartment
10.0(1 Review)
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
- Wheelchair Accessible
US $221/Night
7 Nights - US $1,547
Bed & Breakfast
9.2(1004 Reviews)
1 Bedroom
- Breakfast
- Parking
- Air Conditioner
- Internet
US $195/Night
7 Nights - US $1,367
Apartment
10.0(18 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $185/Night
7 Nights - US $1,297
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $81/Night
7 Nights - US $567
Apartment
10.0(16 Reviews)
1 Bedroom
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $244/Night
7 Nights - US $1,706
Apartment
10.0(12 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $162/Night
7 Nights - US $1,133
Apartment
10.0(10 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $167/Night
7 Nights - US $1,171
Apartment
10.0(8 Reviews)
1 Bedroom
3 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $95/Night
7 Nights - US $666
Milwaukee Private Villas and Holiday Homes Under $200
Over 1431+ Milwaukee Private Villas and Holiday Homes Under $200
Apartment
10.0(26 Reviews)
2 Bedrooms
4 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $175/Night
7 Nights - US $1,223
Apartment
10.0(3 Reviews)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $163/Night
7 Nights - US $1,140
Bed & Breakfast
9.6(471 Reviews)
1 Bedroom
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $171/Night
7 Nights - US $1,199
Apartment
10.0(25 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $192/Night
7 Nights - US $1,341
Apartment
10.0(2 Reviews)
1 Bedroom
4 Guests
- Parking
- Air Conditioner
- Internet
Accessibility
US $179/Night
7 Nights - US $1,251
House
10.0(13 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $191/Night
7 Nights - US $1,334
Apartment
10.0(9 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $143/Night
7 Nights - US $1,001
Cottage
10.0(8 Reviews)
1 Bedroom
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $182/Night
7 Nights - US $1,277
Apartment
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $184/Night
7 Nights - US $1,290
Instantly Bookable Holiday Homes in Milwaukee
Over 1705+ Instantly Bookable Holiday Homes in or Near Milwaukee
Apartment
10.0(29 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $277/Night
7 Nights - US $1,939
Apartment
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Child Friendly
- Wheelchair Accessible
US $60/Night
7 Nights - US $420
US $136/Night
7 Nights - US $954
House
10.0(29 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $239/Night
7 Nights - US $1,675
Cottage
10.0(23 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $249/Night
7 Nights - US $1,743
House
10.0(14 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $242/Night
7 Nights - US $1,692
House
10.0(10 Reviews)
2 Bedrooms
5 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $232/Night
7 Nights - US $1,626
House
10.0(6 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $374/Night
7 Nights - US $2,618
Apartment
10.0(6 Reviews)
2 Bedrooms
8 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $236/Night
7 Nights - US $1,649
Book a Last Minute Place to Stay in Milwaukee
About Casai's Private Villas and Holiday Rentals in Milwaukee
Discover more than 3079 vacation rentals available in Milwaukee. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Milwaukee.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Milwaukee, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Milwaukee. On average, places to stay near Milwaukee offer 739.57 ft², with nightly prices averaging US $384.
With Casai, finding and comparing holiday rentals in Milwaukee is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Milwaukee, WI
There are 3079 Milwaukee, WI Holiday Rentals
- Prices for a holiday home in Milwaukee start at US $48
- Top rated vacation home in Milwaukee is Our Happy Place in Cedarburg, WI
- Most popular short term in Milwaukee is Saint Kate - The Arts Hotel
- Cheapest place to stay in Milwaukee is Super 8 by Wyndham Milwaukee Airport
- Most expensive holiday rental in Milwaukee is Beautiful homes a
Recently Booked Holiday Rentals in Milwaukee
Frequently Asked Questions About Milwaukee?
What are the top holiday rentals in Milwaukee?
With numerous options available in Milwaukee, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Milwaukee:
- Our Happy Place in Cedarburg, WI
- 77 Acre Private Sanctuary near Kettle Moraine Trails, Alpine Valley & History.
- Modern, Spacious Home near Cedarburg - Perfect for Families and Girls' Getaways!
- Beautiful English Mansion, 1/4 mile from Lake and close to Arts & Entertainment
- Sleeps 20, 3 Kings, great fishing. Weekly mid-June-Aug. Rescheduling allowed.
- Nagawicka Woods-Beautiful Lake Country Ranch Home
- Blue Fish Cottage-Hot tub, Kayaks, Ice Fishing
- Luxury Lakefront Home w Miles of Lake Views, private pier, lake toys & game room
- Charming, cozy and CENTRAL upper unit in MKE
- Long-term, Pet-friendly, Kid-friendly Farmhouse near Holy Hill, Kettle Moraine
How many holiday rentals have private pools in Milwaukee?
Discover a selection of holiday rentals with private pools near Milwaukee with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Milwaukee are best for families?
If you're searching for a family-friendly holiday home in Milwaukee, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Milwaukee:
How many Casai.com holiday rentals are available in Milwaukee?
As of 2026, Casai boasts over 3079 properties listed in the Milwaukee area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Milwaukee.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| East Town Vacation Rentals in Milwaukee, Wisconsin | 294 |
| Lower East Side Vacation Rentals in Milwaukee, Wisconsin | 126 |
| Westown Vacation Rentals in Milwaukee, Wisconsin | 94 |
| Fifth Ward Vacation Rentals in Milwaukee, Wisconsin | 88 |
| Yankee Hill Vacation Rentals in Milwaukee, Wisconsin | 78 |
| Brewers Hill Vacation Rentals in Milwaukee, Wisconsin | 26 |
| Riverwest Vacation Rentals in Milwaukee, Wisconsin | 1235 |
| Northpoint Vacation Rentals in Milwaukee, Wisconsin | 1246 |
| Historic Water Tower Vacation Rentals in Milwaukee, Wisconsin | 1120 |
| Historic Third Ward Vacation Rentals in Milwaukee, Wisconsin | 1439 |
| Marquette Vacation Rentals in Milwaukee, Wisconsin | 1364 |
| Concordia Vacation Rentals in Milwaukee, Wisconsin | 1244 |
| Upper East Side Vacation Rentals in Milwaukee, Wisconsin | 1132 |
| Harambee Vacation Rentals in Milwaukee, Wisconsin | 1326 |
| Burnham Park Vacation Rentals in Milwaukee, Wisconsin | 914 |
| Washington Heights Vacation Rentals in Milwaukee, Wisconsin | 468 |
