Holiday Rentals in Winnipeg

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Winnipeg holiday rentals
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Best Holiday rentals and Airbnb offers in Winnipeg

Browse Holiday Rentals near the Historic Centre in Winnipeg

Reconnect with your partner at secluded holiday rentals for couples in Winnipeg, offering intimate settings for a city break.

Modern Downtown 1br | Rooftop & Gym | Jets Games! - Winnipeg
9.3 192 reviews

Modern Downtown 1br | Rooftop & Gym | Jets Games!

apartment, WPG
This modern one-bedroom flat is located in downtown Winnipeg, just a minute's walk from the Canada Life Centre and four blocks from the RBC Convention Centre, making it ideal for exploring the city's main attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
The open-plan living space can comfortably accommodate two guests. The apartment features a fully-equipped kitchen, a comfortable queen-sized bed, a leather sofa, a 40-inch smart TV, and access to a fitness room and stunning rooftop views.
Downtown Luxury Skyloft - Winnipeg
9.3 62 reviews

Downtown Luxury Skyloft

apartment, WPG
This Winnipeg city centre apartment, in the Glasshouse Sky Lofts building, is centrally located within walking distance of the RBC Convention Centre and other attractions in the business district.
The two-bedroom, one-bathroom flat sleeps four guests, offering a fully equipped kitchen, in-suite laundry, high-speed Wi-Fi, and access to a rooftop lounge, gym, and parking (if rented).
Free Parking Luxury 2 Bedroom Condo Downtown - Winnipeg
9.9 709 reviews

Free Parking Luxury 2 Bedroom Condo Downtown

apartment, WPG
This Winnipeg city centre apartment offers superb access to major attractions; Canada Life Centre, True North Square, The Forks National Historic Site, and the Exchange District are all within easy walking distance.
The two-bedroom, one-bathroom flat sleeps four guests and boasts a fully equipped kitchen, in-suite laundry, balcony, 55" smart TV, free secured parking, and access to a fitness centre, home theatre, and rooftop patio.
Village House Unit 7 - Winnipeg
9.9 232 reviews

Village House Unit 7

apartment, WPG
This one-bedroom apartment in Winnipeg's Osborne Village is ideally located within easy walking distance of downtown, The Forks, and a lively neighbourhood filled with restaurants, cafes, and shops. It has received excellent ratings for location, cleanliness, and overall user experience.
The flat is well-suited for couples or solo travellers and features a modern design with a separate living and sleeping area for a peaceful stay. Guests can enjoy a spacious balcony, a fully equipped kitchen, in-unit laundry, and access to a cafe on the ground floor.

Best Winnipeg holiday rentals with air conditioning

Walking 3br Modern House To St Boniface - Winnipeg
9.7 82 reviews

Walking 3br Modern House To St Boniface

apartment, WPG
This Winnipeg apartment is ideally situated near downtown Winnipeg, The Forks National Historic Site, and St. Boniface Hospital, offering easy access to local shops and restaurants.
The three-bedroom, two-bathroom property sleeps six guests in three queen beds and includes an ultramodern kitchen with stainless steel appliances, in-suite laundry, Wi-Fi, and a smart TV; parking is also provided.
Cozy Spacious 1br Basement Suite | Close To U Of M - Winnipeg
10 36 reviews

Cozy Spacious 1br Basement Suite | Close To U Of M

apartment, WPG
This Prairie Pointe, Southwest Winnipeg guesthouse offers a comfortable basement suite, ideally situated in a quiet residential area; further details regarding distances to local landmarks require additional information.
The self-contained apartment features a queen-sized bedroom, shared access to a kitchenette and living area, sleeps up to two guests (with a possible second bedroom upon request), and includes amenities such as complimentary bottled water and a hairdryer.
Ultraclean Luxurious Large Penthouse. Central, Best Location In Winnipeg. - Winnipeg
9.5 162 reviews

Ultraclean Luxurious Large Penthouse. Central, Best Location In Winnipeg.

apartment, WPG
This luxurious three-bedroom penthouse is situated in Winnipeg's Exchange District, just a short walk from the city centre and close to the Saint Boniface Hospital. The apartment has received excellent ratings for location, cleanliness, and user experience.
The penthouse offers 3000 square feet of living space, comfortably accommodating up to six guests. Enjoy a fully equipped kitchen with modern appliances, a private terrace with a BBQ, and a dedicated gym facility within the building.
Luxury Condo Downtown **Parking Spot Included** - Winnipeg
9.7 515 reviews

Luxury Condo Downtown **Parking Spot Included**

apartment, WPG
This Winnipeg city centre apartment is ideally located opposite Canada Life Centre and True North Square, within walking distance of The Forks National Historic Site and the Exchange District.
The 8th-floor suite offers two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen, in-suite laundry, free parking, and a balcony with downtown views.

Frequently asked questions about holiday rentals in Winnipeg

  • What are the top family-friendly attractions in Winnipeg?

    The Assiniboine Park Zoo is always a hit with kids, and there's a great playground right next door. The Manitoba Children's Museum is also a great option for a rainy day, and the Forks is a great place to wander around and enjoy the river.
  • What are the best Airbnb and holiday rentals in Winnipeg?

  • When is the best time to book a vacation rental in Winnipeg?

    The best time to book a vacation rental in Winnipeg is during the shoulder seasons, in the spring or autumn. You'll avoid the crowds and the prices will be lower, plus the weather is usually pleasant.
  • What are the most popular Airbnbs in Winnipeg?

  • What events or festivals should visitors check out in and around Winnipeg?

    Winnipeg is known for its vibrant arts and culture scene. The Winnipeg Fringe Theatre Festival in July is a great way to experience the city's creativity, and the Folklorama festival in August is a celebration of Winnipeg's diverse cultural heritage.
  • What are the best holiday rentals with a pool in Winnipeg?

  • What are the best budget-friendly activities in Winnipeg?

    The Forks is a great place to spend a day, with free concerts and events happening regularly. You can also take a free walking tour of the city, or visit one of the many free museums in Winnipeg.
  • What are the best rentals for families and kids in Winnipeg?

    The best rentals for families and kids in Winnipeg are (2001)glasshouse Impressive 1 Bdr Suite (311), Theloftonjames and St Boniface Residence.

  • What are the best restaurants with local dishes in Winnipeg?

    For a taste of Winnipeg's culinary scene, you should try the traditional dishes at The Common, or enjoy a hearty meal at The King's Head Pub. If you're looking for something a bit more modern, try out the innovative dishes at Enoteca.
  • What are the best rentals or Airbnbs with a jacuzzi in Winnipeg?

  • What are the best walking or cycling routes in Winnipeg?

    The Assiniboine River Trail is a great option for a scenic walk or bike ride, and the Red River Trail is another popular choice. For a more urban experience, try the loop around the downtown area.
  • Are there pet-friendly attractions in Winnipeg?

    Many of Winnipeg's parks are dog-friendly, including the Assiniboine Park. You can also take your furry friend to the Winnipeg Farmers' Market, where there are plenty of treats for both of you.
  • What are the benefits of choosing a vacation rental in Winnipeg?

    Vacation rentals offer more space and privacy than hotels, and are often more affordable, especially for families or groups. You'll also have access to a kitchen, which can be a big plus if you're planning on doing some of your own cooking.

Popular destinations

Check Out Holiday Rentals with a Balcony in Winnipeg

A terrace with city skyline views is a fantastic reason to book a holiday rental in Winnipeg. View our top picks and start comparing now.

The Ivory House | Elegant 3br Home Near U Of M & Downtown - Winnipeg
No reviews

The Ivory House | Elegant 3br Home Near U Of M & Downtown

apartment, WPG
This three-bedroom flat in Winnipeg's Fort Garry district is a 3-minute drive from Thermëa Wellness Centre and Destination Dinner Stage, offering convenient access to local attractions.
This family-friendly apartment accommodates up to six guests with two bathrooms, a full kitchen, complimentary Wi-Fi, and on-site parking, plus a private terrace for relaxation.
20th Floor Downtown Condo | 2 Bed | 1 Bath | - Winnipeg
No reviews

20th Floor Downtown Condo | 2 Bed | 1 Bath |

apartment, WPG
This two-bedroom flat offers a prime downtown Winnipeg location, situated a short 500-meter walk from the Canada Life Centre and True North Square, with skywalk access to dining and the arena, and within walking distance of the historic Exchange District and The Forks.
Spanning 71 square meters, this apartment accommodates up to four guests and features floor-to-ceiling windows, a fully equipped kitchen, ensuite laundry, high-speed WiFi, and access to building amenities including a rooftop patio and theatre room, with secure parking available.
Luxury Tuxedo Family Home With Hot Tub - Winnipeg
9.8 48 reviews

Luxury Tuxedo Family Home With Hot Tub

apartment, WPG
The Cheerful Tuxedo House is situated in Winnipeg's upscale Tuxedo neighbourhood, offering convenient access to Outlet Collection Winnipeg and Polo Park shopping centres, and is within easy reach of the Canada Life Centre and Celebrations Dinner Theatre.
This five-bedroom, four-bathroom property boasts 316 square metres of living space, accommodating up to twelve guests and featuring a jacuzzi, air conditioning, and a fully equipped kitchen including a dishwasher; enjoy its two living rooms, sunroom, and outdoor hot tub.
Lakeview 2 Bedroom Walkout Suite With Trail View - Winnipeg
No reviews

Lakeview 2 Bedroom Walkout Suite With Trail View

apartment, WPG
This detached suite is located in Winnipeg's Fort Garry district, offering lake views and direct access to a walking trail, with convenient proximity to Outlet Collection Winnipeg and Polo Park, both within 5 kilometers.
This 121 square meter apartment features two bedrooms, accommodating up to five guests with a fully equipped kitchen, in-suite laundry, private parking, and a dedicated workspace, making it ideal for a comfortable stay.

Discover Family-Friendly Self-Catering Rentals in Winnipeg

Getting the holiday rental right makes all the difference for a family trip to Winnipeg. Find city attractions within easy reach. Start comparing now.

Cozy 2-bedroom Basement Suite - Winnipeg
9.7 3 reviews

Cozy 2-bedroom Basement Suite

house, WPG
This 2-bedroom basement apartment is located at 35 Namarik Wy, Winnipeg, in a quiet residential area.
This family-friendly apartment offers 225 square meters of space for up to 10 guests, featuring a kitchenette, air conditioning, free WiFi, and private parking, with entertainment options including a PS4 and streaming services.
70 M² House ∙ 2 Bedrooms ∙ 5 Guests - Winnipeg
No reviews

70 M² House ∙ 2 Bedrooms ∙ 5 Guests

house, WPG
This private basement flat is located in Winnipeg's quiet Devonshire neighbourhood, offering a peaceful residential setting.
This two-bedroom, one-bathroom dwelling accommodates up to five guests and features a kitchenette, high-speed Wi-Fi, and in-suite laundry for stays of three nights or more.
Luxury Two Bedrooms - Winnipeg
8.0 20 reviews

Luxury Two Bedrooms

apartment, WPG
This Winnipeg apartment, situated near the southern edge of the city, is 6-19 kilometres from attractions including Investors Group Field, Kings Park, The Forks Market, and the Canadian Museum for Human Rights.
The one-bedroom, one-bathroom flat offers self-catering facilities for up to seven guests, including a fully equipped kitchen, complimentary high-speed Wi-Fi, air conditioning, private parking, and access to a garden.
Bonavista Light House Deluxe Max - Winnipeg
9.8 55 reviews

Bonavista Light House Deluxe Max

apartment, WPG
This five-bedroom house, situated in Bonavista, South Winnipeg, is conveniently located near Sage Creek Mall, approximately 21km from the University of Manitoba, 32km from Winnipeg city centre, and 16km from St. Vital Mall.
The spacious property boasts three living rooms, sleeps thirteen guests, includes a fully equipped kitchen with a 36-inch Samsung fridge, and offers a large double-layer deck overlooking a lake.

Compare Holiday Rentals with Parking in Winnipeg

On-site parking takes one thing off your list when visiting Winnipeg. Our holiday rentals have it included.

Comfortable Home Near Airport - Winnipeg
9.7 111 reviews

Comfortable Home Near Airport

apartment, WPG
5 Bed 4 Bath 2500 Sqft Clean And Elegant Home - Winnipeg
9.5 228 reviews

5 Bed 4 Bath 2500 Sqft Clean And Elegant Home

apartment, WPG
Luxury Loft In Osborne Village - Heated Parking - Winnipeg
9.9 40 reviews

Luxury Loft In Osborne Village - Heated Parking

apartment, WPG
3br W/ King Beds & Modern Kitchen  South Winnipeg - Winnipeg
9.6 114 reviews

3br W/ King Beds & Modern Kitchen South Winnipeg

apartment, WPG

Explore 5-Star Self-Catering Rentals in Winnipeg

Upscale holiday rentals in Winnipeg offer a refined stay you will want to return to. Enjoy premium amenities and attentive service.

Royal Oak - 2-bedroom (King & Queen Bed), Living Area, Kitchen And Full Bathroom - Winnipeg
9.4 8 reviews

Royal Oak - 2-bedroom (King & Queen Bed), Living Area, Kitchen And Full Bathroom

apartment, WPG

Top Pet-Friendly Holiday Rentals in Winnipeg

Travelling with a pet to Winnipeg is easy when your holiday rental is properly set up with nearby dog parks and city walks.

Cozy Winnipeg Getaway - Near The Forks & Hospital - Winnipeg
9.4 127 reviews

Cozy Winnipeg Getaway - Near The Forks & Hospital

apartment, WPG
Spacious 2- Floor Wolseley Residence | 2br | 2ba - Winnipeg
10 147 reviews

Spacious 2- Floor Wolseley Residence | 2br | 2ba

apartment, WPG
Modern 2br  Near Canada Life Centre  Parking - Winnipeg
9.6 103 reviews

Modern 2br Near Canada Life Centre Parking

apartment, WPG
Comfy |4 Bedroom| Family Getaway - Winnipeg
9.3 46 reviews

Comfy |4 Bedroom| Family Getaway

apartment, WPG

Choose the Right Holiday Rentals with a Pool in Winnipeg

Pool access at your holiday rental makes a proper swim in the heart of the city part of your daily routine in Winnipeg.

Chic Suite | Sauna | Heart Of Downtown - Winnipeg
9.4 19 reviews

Chic Suite | Sauna | Heart Of Downtown

apartment, WPG
Relax To The Max + Stay & Play In The Lap Of Luxury - Winnipeg
9.9 267 reviews

Relax To The Max + Stay & Play In The Lap Of Luxury

apartment, WPG
Sept Pool Open, Backyard Oasis Garage/drive - Winnipeg
10 106 reviews

Sept Pool Open, Backyard Oasis Garage/drive

apartment, WPG
65 M² House ∙ 1 Bedroom ∙ 2 Guests - Winnipeg
No reviews

65 M² House ∙ 1 Bedroom ∙ 2 Guests

house, WPG

Guest-Favourite Holiday Rentals with a Hot Tub in Winnipeg

There is a real magic to having a private hot tub after exploring Winnipeg. Browse available holiday rentals below.

Waterfront Views And Tranquil Neighborhood - Winnipeg
9.8 7 reviews

Waterfront Views And Tranquil Neighborhood

apartment, WPG
Modern House, Close To All Amnts In South King Bd - Winnipeg
10 114 reviews

Modern House, Close To All Amnts In South King Bd

apartment, WPG
Executive Downtown Comfort With Amenities Galore - Winnipeg
9.9 326 reviews

Executive Downtown Comfort With Amenities Galore

apartment, WPG
Riverfront Retreat With Hot Tub, Dock & Sunroom - Winnipeg
10 8 reviews

Riverfront Retreat With Hot Tub, Dock & Sunroom

apartment, WPG
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