Vacation rentals in Headingley

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Top-rated vacation rentals in Headingley

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

Guest favorite

Home in Winnipeg

5.0 out of 5 average rating, 42 reviews

Winnipeg Perfect Vacation House

Gorgeous bungalow w/ open concept features 1 comfy king size Bdrm, and 2 queen size Bdrms, a full kitchen, WiFi access, smart TV, Netflix. The kitchen is truly the jewel of this home w/ a stunning island, SS appliances and quartz counters. A beautifully bath w/ glass shower doors. Spacious backyard and patio, gazebo w/ BBQ to enjoy our summers day. Great home located in one of the safest and quiet yet central neighborhood. Close to many amenities, Polo Park mall & Airport. Bus routes available

Apr 3 – 10

R2,700 ZAR per night
Guest favorite

Townhouse in Winnipeg

4.75 out of 5 average rating, 158 reviews

❤️ Fast CHECK-IN ❤️ 4 Bdr & 4 Beds, House.

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

Nov 14 – 21

R2,794 ZAR per night
Guest favorite

Home in Winnipeg

4.9 out of 5 average rating, 31 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 are numerous restaurants, also St. James civic centre with the pool and activities (only 15 min walking). Additionally, around 5-10 mins drive to The Assiniboine Zoo Park, Sargent Sundae, and Living Prairie Museum. Your family will be close to everything when you stay at this centrally located place.

Jun 8 – 15

R2,300 ZAR per night

Popular amenities for Headingley vacation rentals

Other great vacation rentals in Headingley

Guest favorite

Guest suite in Winnipeg

5.0 out of 5 average rating, 8 reviews

Beautiful 1 Bedroom suite near the airport

Dec 8 – 15

R1,299 ZAR per night
Superhost

Home in Winnipeg

4.79 out of 5 average rating, 43 reviews

Full Home in Winnipeg

Dec 27 – Jan 3

R1,856 ZAR per night
Superhost

Home in Winnipeg

4.78 out of 5 average rating, 27 reviews

Lower Level One Bedroom Suite

Sep 16 – 23

R1,445 ZAR per night
Guest favorite

Guesthouse in Winnipeg

4.91 out of 5 average rating, 11 reviews

“Grandpa’s Side” Private In-Home Suite

Jun 6 – 13

R1,299 ZAR per night

Home in Winnipeg

4.8 out of 5 average rating, 5 reviews

Spacious bungalow with basement

Apr 22 – 29

R2,018 ZAR per night

Home in Winnipeg

4.7 out of 5 average rating, 44 reviews

Basement Apartment - Winnipeg

Jan 2 – 9

R1,149 ZAR per night

Home in Winnipeg

4.94 out of 5 average rating, 17 reviews

Luxury 3 bedroom with HOT TUB!

Apr 21 – 28

R2,862 ZAR per night

Bungalow in Winnipeg

4.8 out of 5 average rating, 10 reviews

Luxury Bright 5 Bedroom Bungalow (Great Location)

May 7 – 14

R3,894 ZAR per night
Guest favorite

Home in Winnipeg

4.9 out of 5 average rating, 31 reviews

Airport Haven! 2BR Stylish Home!

Sep 20 – 27

R2,122 ZAR per night
Guest favorite

Guest suite in Winnipeg

4.7 out of 5 average rating, 27 reviews

Beautiful basement suite in bi-level house

Dec 30 – Jan 6

R896 ZAR per night

Bungalow in Winnipeg

4.75 out of 5 average rating, 4 reviews

Bungalow house in Winnipeg

Aug 12 – 19

R2,076 ZAR per night

Farm stay in Winnipeg

4.6 out of 5 average rating, 5 reviews

Right from the FARM

Apr 4 – 11

R3,592 ZAR per night
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