Holiday rentals in Headingley

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Top-rated holiday rentals in Headingley

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Guest suite in Headingley

4.97 out of 5 average rating, 70 reviews

Private Luxury 2 bedrooms Basement Suite Winnipeg

New Fully Furnished Basement suite This suites offer 📌 2 bedrooms (1 King Size and 1 Queen Size) 📌 1 Full washroom 📌 spacious Living Area 📌 Large Kitchen 📌 Dining area 📌 Led Tv 4K UHD 65 Inches with Netflix 📌 Separate Entrance 📌 Lit path 📌 Free 24 Hrs Parking 📌 Free WiFi Welcome to our New Suite nestled in Very peaceful neighbourhood in Blumberg Trail Just Stones throw away from Trans Canada Hyw 1. Whether you're here for a relaxing getaway our location ensures Privacy nd convenience.

Superhost

Bungalow in Winnipeg

4.78 out of 5 average rating, 54 reviews

Luxury Bright 5 Bedroom Bungalow (Great Location)

Luxurious 5 bedroom bungalow 3500sqft living space, REC ROOM/DBL ATTACH GARAGE, Sleep upto 10 people. Park-like yard. The luxurious feel starts from the entry with marble like tile floors, large windows, modern chandeliers. Full service kitchen.The Master has walk in closet & 5 piece ensuite. The main bathroom is 4 piece with skylight. 15-20 minutes to airport, downtown, hospitals, University etc Located near Assiniboine Park, Zoo, Forest, Shopping at Seasons of Tuxedo, IKEA, lots of restaurants

Guest favourite

Home in Winnipeg

4.98 out of 5 average rating, 164 reviews

Albany Cottage: loft bedroom and close to airport

Take it easy at this cottage style home located on a quiet residential street just 10 minutes west of Downtown Winnipeg and 5 minutes from the James Armstrong Richardson International Airport. Albany Cottage, built in 1907, offers a loft bedroom and office plus a breezy boho porch for enjoying your morning coffee. Public transportation and bike/walking trails are right at the end of the street, and you are a 10-minute walk from one of Winnipeg's most popular public spaces, Assiniboine Park.

Superhost

Townhouse in Winnipeg

4.78 out of 5 average rating, 103 reviews

*Bali-Peg* Luxury Accommodation

TOP 10 WINNIPEG VACATION & HOLIDAY HOMES Our vetted home has been approved for comfort and quality. It is fully furnished, with well-equipped kitchens, luxury bathroom toiletries, and all linen included. Available for both short and long-term stays. Perfect location in a peaceful neighborhood! You will have FREE access to Wifi✔ Smart TV✔ Parking✔ Washer&Dryer✔ And much more✔ - Easy and fast access to the house via a Smart Lock - 4 Beds, 4 Bedrooms, 7 Sleeping spots - 9 am to 9 pm Support

Guest favourite

Home in Winnipeg

4.92 out of 5 average rating, 75 reviews

SweetHome Airport 7', Central 15'

Welcome to this comfortable family and kid-oriented home which is 7 min to Airport, 5 min to Polo Park mall, 15 min to the downtown business district, Canada Life Centre, the Forks & Museums. There're many restaurants, parks and also St. James civic centre with the pool (15 min walk). Additionally, ~5-10 mins drive to The Assiniboine Zoo Park, Sargent Sundae, and Living Prairie Museum. Your family will be close to everything while staying at this centrally located place. STRA-2024-2507455

Guest favourite

Home in Winnipeg

4.95 out of 5 average rating, 222 reviews

Entire Suite in Crestview

Welcome to our amazing new suite nestled in a peaceful neighborhood in Crestview, just a stone's throw away from Winnipeg's finest dining establishments and shopping centers. Whether you're here for a relaxing getaway or a business trip, our location ensures convenience and tranquility. Situated a mere 15-minute drive from Winnipeg Airport and Polo Park, our suite is easily accessible. As part of a new duplex-style home, this unit offers complete privacy with its own separate entrance.

Guest favourite

Home in Winnipeg

4.87 out of 5 average rating, 45 reviews

New Renovated Home With Jacuzzi

Our carefully inspected property has been approved for both comfort and quality. It is completely outfitted with upscale bathroom fixtures and fully functional kitchens. Fantastic location in a calm And really handy place! Free street parking, be aware that the City sometimes can prohibit the parking for the night because of the snow removal, etc, Among other things, a washer and dryer. - Easy and quick access to the house with a smart lock 9 a.m. to 9 p.m.: Assistance is offered.

Guest favourite

Home in Winnipeg

4.91 out of 5 average rating, 117 reviews

2022 House Build! 3 King Beds 2.5 Baths!

Welcome to your home away from home. This is a newer build, 2 storey private suite. All 3 bedrooms are furnished with king beds! Walking distance to some of Winnipeg's finest attractions including Assiniboine Park/Zoo, Sargent Sundae and just a few doors down from The Burger Place. Minutes away from Polo Park shopping mall, groceries and restaurants. This open concept suite comes equipped with everything you need to make your stay enjoyable, including Netflix and in suite laundry.

Guest favourite

Home in Winnipeg

4.9 out of 5 average rating, 20 reviews

Bungalow House Winnipeg -Short Term Rental

Kick back and relax in this calm, stylish space. Enjoy a stylish experience at this centrally located place. Accessible for both transient and long-term stays. Excellent location in a calm but extremely convenient neighborhood! Welcome to your temporary residence! The full house at our tastefully furnished Airbnb is ideal for a convenient and comfortable short or long stay. This house provides everything you need to feel at home, whether you're traveling for work or pleasure.

Guest favourite

Guest suite in Winnipeg

4.98 out of 5 average rating, 62 reviews

The Guest Expertise Luxury 2BR Retreat

Luxurious Stay Perfect for Group Trips Only 5 minutes from No Frills and Walmart Nearby access to Outlet Mall, Ikea, community center, parks, golf course, YMCA, restaurants, shopping, and hotels. Nestled in a truly beautiful and peaceful neighborhood. Access to the basement is through the main door, but a separate entrance maintains your privacy. Please note my family resides in the main part of the house. Ready to relax in style and convenience? Book your stay today!

Superhost

Home in Winnipeg

4.78 out of 5 average rating, 78 reviews

Winnipeg Top Stay

Welcome to your home away from home! We offer comfortable accommodation in the perfect spot. Our property features high end modern, open concept living area, 3 bedrooms with comfy queen beds and 2 full bathrooms. Fully loaded kitchen w/ high-end stainless steel appliances and dishwasher. WIFI access throughout the space, Smart TVs, Netflix. Lots of vanity counter space! Our guests can enjoy the bbq and in the spacious backyard. Great for small groups or families.

Guest favourite

Bungalow in Winnipeg

4.94 out of 5 average rating, 35 reviews

Banff-Themed King Size Retreat

Welcome to our Airbnb listing for Winnipeg! Our modest home in the quaint Charleswood area with a rustic Banff-inspired interior that transports you to the Rockies right in the middle of the city. Unwind in our inviting living room, which features plush armchairs and a big flat-screen TV. Your group will have enough room in the dining area, and the fully equipped kitchen is ideal for creating delectable meals. We wish you a relaxing and memorable stay with us!