Condo
10.0(94 Reviews)
1 Bedroom
2 Guests
Parking
Kitchen
Air Conditioner
Internet
CA $223/Night
7 Nights - CA $1,561
Winnipeg Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Winnipeg
10.0
Apartment
10.0(11 Reviews)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
Child Friendly
CA $109/Night
7 Nights - CA $761
House
10.0(1 Review)
1 Bedroom
- Parking
- Internet
- Child Friendly
Wellness Facilities
CA $148/Night
7 Nights - CA $1,033
Condo
10.0(69 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $513/Night
7 Nights - CA $3,592
Apartment
10.0(6 Reviews)
3 Bedrooms
6 Guests
- Parking
- Air Conditioner
- Internet
Laundry
CA $221/Night
7 Nights - CA $1,546
House
10.0(40 Reviews)
2 Bedrooms
4 Guests
- Parking
Balcony/Terrace- Kitchen
- Air Conditioner
CA $338/Night
7 Nights - CA $2,369
House
10.0(34 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $131/Night
7 Nights - CA $920
House
10.0(23 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $223/Night
7 Nights - CA $1,563
House
10.0(17 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $266/Night
7 Nights - CA $1,862
Luxury Holiday Rentals in Winnipeg
Over 1353+ Luxury Holiday Rentals in or Near Winnipeg
House
2 Bedrooms
5 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
Unlock the Best Price
House
2 Bedrooms
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $5,691/Night
7 Nights - CA $39,837
New
House
6 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $2,134/Night
7 Nights - CA $14,939
House
2.0(1 Review)
3 Bedrooms
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $1,865/Night
7 Nights - CA $13,056
Villa
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $1,715/Night
7 Nights - CA $12,006
House
10.0(2 Reviews)
6 Bedrooms
18 Guests
- Parking
- Balcony/Terrace
- Internet
- Child Friendly
CA $1,437/Night
7 Nights - CA $10,060
House
9.8(48 Reviews)
6 Bedrooms
14 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
CA $1,388/Night
7 Nights - CA $9,716
House
2.0(1 Review)
4 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $1,353/Night
7 Nights - CA $9,467
CA $1,350/Night
7 Nights - CA $9,451
Top-Rated Holiday Rentals with a Pool in Winnipeg
Over 88+ The Best Private Villas and Holiday Rentals in Winnipeg with a Pool
Hotel
9.6(1001 Reviews)
Breakfast- Parking
Pool- Kitchen
CA $299/Night
7 Nights - CA $2,094
Bed & Breakfast
9.4(251 Reviews)
1 Bedroom
- Hot Tub
- Parking
- Pool
Spa
CA $212/Night
7 Nights - CA $1,483
House
9.4(90 Reviews)
3 Bedrooms
10 Guests
- Parking
- Pool
- Spa
- Balcony/Terrace
CA $156/Night
7 Nights - CA $1,090
Hotel
9.2(1657 Reviews)
- Parking
- Pool
- Kitchen
- Air Conditioner
CA $169/Night
7 Nights - CA $1,183
CA $161/Night
7 Nights - CA $1,124
CA $190/Night
7 Nights - CA $1,328
CA $210/Night
7 Nights - CA $1,473
CA $193/Night
7 Nights - CA $1,352
Pet-Friendly Holiday Rentals in Winnipeg
Over 336+ Pet-Friendly Holiday Rentals in or Near Winnipeg
House
10.0(1 Review)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $52/Night
7 Nights - CA $363
House
10.0(2 Reviews)
5 Bedrooms
11 Guests
- Parking
- Balcony/Terrace
View- Kitchen
CA $657/Night
7 Nights - CA $4,598
Apartment
1 Bedroom
- Kitchen
- Air Conditioner
Pet Friendly- Child Friendly
CA $76/Night
7 Nights - CA $533
House
9.8(12 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $199/Night
7 Nights - CA $1,391
Apartment
9.5(2 Reviews)
3 Bedrooms
6 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
CA $194/Night
7 Nights - CA $1,358
Apartment
9.8(10 Reviews)
1 Bedroom
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $245/Night
7 Nights - CA $1,717
House
9.8(9 Reviews)
1 Bedroom
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
CA $495/Night
7 Nights - CA $3,468
Condo
9.8(7 Reviews)
1 Bedroom
3 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
CA $219/Night
7 Nights - CA $1,532
House
9.8(6 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $321/Night
7 Nights - CA $2,248
Large Holiday Rentals and Private Villas in Winnipeg
Over 61+ Large Holiday Rentals and Private Villas in or Near Winnipeg
Apartment
9.2(5 Reviews)
2 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $73/Night
7 Nights - CA $509
Bed & Breakfast
9.7(425 Reviews)
5 Bedrooms
12 Guests
- Breakfast
- Parking
- Balcony/Terrace
- View
CA $287/Night
7 Nights - CA $2,010
CA $201/Night
7 Nights - CA $1,409
House
9.5(4 Reviews)
6 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
CA $251/Night
7 Nights - CA $1,757
House
10.0(8 Reviews)
5 Bedrooms
13 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $496/Night
7 Nights - CA $3,473
Condo
9.8(18 Reviews)
5 Bedrooms
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $284/Night
7 Nights - CA $1,989
House
9.8(10 Reviews)
5 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $383/Night
7 Nights - CA $2,683
House
9.6(5 Reviews)
5 Bedrooms
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $463/Night
7 Nights - CA $3,243
House
9.6(4 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
CA $603/Night
7 Nights - CA $4,224
Wheelchair Accessible Holiday Homes in Winnipeg
Over 181+ Wheelchair Accessible Holiday Homes in or Near Winnipeg
Condo
10.0(7 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $211/Night
7 Nights - CA $1,475
Bed & Breakfast
10.0(4 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
CA $180/Night
7 Nights - CA $1,257
Hotel
9.4(927 Reviews)
- Breakfast
- Parking
- Kitchen
- Air Conditioner
CA $183/Night
7 Nights - CA $1,282
Condo
10.0(3 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $74/Night
7 Nights - CA $517
Hotel
9.2(292 Reviews)
Private Pool- Hot Tub
- Breakfast
- Parking
CA $232/Night
7 Nights - CA $1,626
Condo
9.6(33 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $239/Night
7 Nights - CA $1,675
Condo
9.6(19 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $254/Night
7 Nights - CA $1,775
Apartment
9.2(5 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $268/Night
7 Nights - CA $1,879
Apartment
8.8(32 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $263/Night
7 Nights - CA $1,842
Winnipeg Private Villas and Holiday Homes Under $200
Over 1142+ Winnipeg Private Villas and Holiday Homes Under $200
Condo
10.0(16 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $270/Night
7 Nights - CA $1,889
Apartment
10.0(5 Reviews)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
Accessibility
CA $112/Night
7 Nights - CA $781
House
10.0(16 Reviews)
1 Bedroom
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $198/Night
7 Nights - CA $1,389
House
10.0(13 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
CA $208/Night
7 Nights - CA $1,455
House
10.0(13 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $198/Night
7 Nights - CA $1,383
House
10.0(11 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $134/Night
7 Nights - CA $940
House
10.0(9 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $180/Night
7 Nights - CA $1,258
Instantly Bookable Holiday Homes in Winnipeg
Over 717+ Instantly Bookable Holiday Homes in or Near Winnipeg
Apartment
10.0(4 Reviews)
2 Bedrooms
3 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
CA $239/Night
7 Nights - CA $1,671
Condo
8.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $182/Night
7 Nights - CA $1,278
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $292/Night
7 Nights - CA $2,046
House
10.0(3 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $184/Night
7 Nights - CA $1,289
Apartment
10.0(3 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $169/Night
7 Nights - CA $1,184
Apartment
10.0(3 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $166/Night
7 Nights - CA $1,164
Apartment
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $162/Night
7 Nights - CA $1,137
House
10.0(3 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $119/Night
7 Nights - CA $832
House
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $242/Night
7 Nights - CA $1,695
Book a Last Minute Place to Stay in Winnipeg
About Casai's Private Villas and Holiday Rentals in Winnipeg
Discover more than 1362 vacation rentals available in Winnipeg. 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 Winnipeg.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winnipeg, 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 Winnipeg. On average, places to stay near Winnipeg offer 565.42 ft², with nightly prices averaging CA $214.
With Casai, finding and comparing holiday rentals in Winnipeg 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 in Winnipeg, MB
There are 1362 Winnipeg, MB Holiday Rentals
- Prices for a holiday home in Winnipeg start at CA $44
- Top rated vacation home in Winnipeg is FREE PARKING NY Style Condo in Exchange District
- Most popular short term in Winnipeg is Travelodge by Wyndham Winnipeg East
- Cheapest place to stay in Winnipeg is Home
- Most expensive holiday rental in Winnipeg is Suite with facilities to make you feel at home
Frequently Asked Questions About Winnipeg?
What are the top holiday rentals in Winnipeg?
With numerous options available in Winnipeg, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winnipeg:
- FREE PARKING NY Style Condo in Exchange District
- theLOFTonJAMES, Historic Exchange District, Exposed Brick & Beams, High Ceilings
- Heritage Red River stone house built by Thomas Bunn in 1862
- Luxurious House in a Desired Location, King Bed
- King Bed Astounding Cinematic Sunset in trendy location, South City
- Lovely St Boniface home w/king bed + private yard
- Modern house in trendy location in South Winnipeg-Bridgwater Area
- Cozy 2-Bedroom basement Suite with Private entrance South Winnipeg.
- Home on large park like lot. Close to beaches, Prov parks & festival grounds.
- Bonavista Light House; a 2 bedroom Serene Suite
How many holiday rentals have private pools in Winnipeg?
Discover a selection of holiday rentals with private pools near Winnipeg 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 Winnipeg are best for families?
If you're searching for a family-friendly holiday home in Winnipeg, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winnipeg:
How many Casai.ca holiday rentals are available in Winnipeg?
As of 2026, Casai boasts over 1362 properties listed in the Winnipeg area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winnipeg.
Nearby Neighborhood (7)
| Neighborhood | Property Count |
|---|---|
| Fort Gary Vacation Rentals in Winnipeg, Manitoba | 589 |
| Downtown Winnipeg Vacation Rentals in Winnipeg, Manitoba | 45 |
| St. James Vacation Rentals in Winnipeg, Manitoba | 212 |
| Exchange District Vacation Rentals in Winnipeg, Manitoba | 575 |
| Regent Vacation Rentals in Winnipeg, Manitoba | 182 |
| West St. Paul Vacation Rentals in Winnipeg, Manitoba | 40 |
| Legislature Vacation Rentals in Winnipeg, Manitoba | 595 |
