Owner Direct Vacation
Rentals in Winnipeg
The Best Owner Direct Vacation Rentals in Winnipeg. Explore thousands of vacation home rentals, large cabins, and villas near Winnipeg
GUESTS
Explore the Best Winnipeg Vacation Homes
Looking for the perfect place to stay in Winnipeg? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Winnipeg character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Pool
- Private Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Pet Friendly
- View
- Air Conditioner
- Parking
- Accessibility
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Security/Safety
- Internet
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
Why Travelers Love Using
Owner Direct to
Find Winnipeg Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Winnipeg
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Security/Safety
Popular Neighborhoods for Winnipeg Vacation Rentals
What are the best areas to stay in Winnipeg
Discover the top neighborhoods in Winnipeg and choose a place that suits your stay.
Sunday Feb 8
Winnipeg, Manitoba
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Winnipeg vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Winnipeg
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
How to Reserve Your Winnipeg Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Winnipeg Vacation Rental FAQs
1. What are the top vacation rentals in Winnipeg?
There are a lot of options in Winnipeg. If you plan on staying in the Winnipeg area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winnipeg:
- NEW ! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !
- FREE PARKING NY Style Condo in Exchange District
- theLOFTonJAMES, Historic Exchange District, Exposed Brick & Beams, High Ceilings
- NEW ! SPACIOUS ULTRA STYLISH 1450sf 2 BR 2 BA CONDO— HISTORIC OSBORNE VILLAGE.
- King Bed Astounding Cinematic Sunset in trendy location, South City
- Modern Home In Central River Heights
- Luxurious House in a Desired Location, King Bed
- Lovely St Boniface home w/king bed + private yard
- Modern house in trendy location in South Winnipeg-Bridgwater Area
- Bonavista Light House; a 2 bedroom Serene Suite
2. How many vacation rentals have private pools in Winnipeg?
There are 39 vacation rentals with private pools near Winnipeg. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Winnipeg are best for families?
If you are looking for a family-friendly vacation home in Winnipeg, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winnipeg:
4. How many vacation rentals are available in Winnipeg?
Currently, the total number of properties listed in 2026 is over 1137 in the Winnipeg area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Winnipeg.