Holiday rentals with a pool in Winnipeg

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Winnipeg

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite

Home in Winnipeg

4.98 out of 5 average rating, 61 reviews

Pool season ! Kg bed, Pet friendly & attached Grg

ElijahRating, 5 stars1 week ago

My partner and I thoroughly enjoyed our stay at Sandy's house! Our check in was easy and we instantly felt so relaxed. Everything was set up beautifully and was easy to find. Sandy was a phenomenal host and was very friendly and communicative throughout our stay. The house and property were immaculate and felt so well taken care of. We were drawn in to rent by the pool and hot tub, but the rest of the house made everything feel that much more special. Our dog loved the space in the back yard and we really enjoyed spending our days by the pool together. I would definitely recommend anyone to stay at Sandy's house!

Home in Winnipeg

3.67 out of 5 average rating, 3 reviews

Exclusive Luxury 4Br Villa w/ Pool & Table Tennis

TamaraRating, 5 stars4 weeks ago

I had a fantastic experience at this Airbnb! The location was ideal, with everything I needed just a short walk away. The place was clean and well-maintained, and the cozy bed was super comfortable. I would definitely recommend this spot for anyone looking for a convenient and relaxing stay!

Guest favourite

Apartment in Winnipeg

4.91 out of 5 average rating, 171 reviews

Lap of Luxury - New 2 Bdrm w Free Bonus Amenities

Live. Play. Stay or simply Relax to the Max in the Lap of Luxury, Terraces of Tuxedo. Winnipeg's most affluent and desirable neighbourhood - safe, clean, quiet yet, close to everything travellers are looking for. Surrounded by generational wealth, Tuxedo turns her nose to the rest. Discover her new sister - the Seasons of Tuxedo for some of the best shopping. Or find her old friend, the Assiniboine Forest for a forage not far from your door. Look at the latest upgrades 01/08/2024!!

Guest favourite

Tiny home in Richer

4.89 out of 5 average rating, 258 reviews

Little Western Cabin

Need a place to relax with your significant other, or maybe just get away on your own? Book your getaway to this cozy little Western Cabin. Located in Wild Oaks Campground this cabin is the perfect place to connect with nature and each other. Take a dip in the pond during the summer months, or enjoy the hot tub and pool. Bring your snow shoes in the winter and enjoy a hike outside on one of our many trails, or get cozy by the campfire.(Hot tub/pool is not available during the winter months)

Guest favourite

Flat in Winnipeg

4.92 out of 5 average rating, 12 reviews

Cozy &Modern Stay Great Location

Have fun with the whole family at this stylish and cozy space! Perfect for families or small groups, this modern apartment offers a comfy living area, fully equipped kitchen, and relaxing bedrooms—all designed with your comfort in mind. Enjoy fast Wi-Fi, smart TV, and a welcoming vibe that feels just like home. Located in a safe, convenient neighborhood close to shops, restaurants, and attractions. Book your stay and make great memories! *24/7 Host Support available! *Great location

Guest favourite

Apartment in Downtown Winnipeg

4.92 out of 5 average rating, 221 reviews

Executive Downtown Comfort with amenities galore

Thoughtfully decorated with all the conveniences of home. Whether working or just relaxing, you will surely love the balcony with barbecue, hot tub, sauna, or gym. Heated indoor parking for mid sized vehicle, sorry no trucks. Main floor of the building is connected to a convenience store, restaurant, and vape shop. Within walking distance of the art gallery, MTS, & Convention Centre , the Forks, & Osborne Village with trendy shops and restaurants. 2 day min. stay. Welcome!

Guest favourite

Guest suite in Winnipeg

4.93 out of 5 average rating, 102 reviews

The Luxe on Vista

This stylish place to stay is perfect for couples ! Sorry, no parties at all. You will love this getaway in St.Vital ! You have a private entrance to your 2 bedroom , 1 bath , full kitchen , living and dining room with a wood burning fireplace! Outside you’ll find your brand new 94 jet hot tub , a bar and a heated salt water pool with diving board ! Enjoy the bbq and have an amazing vacation. Pool is seasonal and closes beginning of October and reopens May. Hot tub is year round

Cabin in Warren

Camping Cabin at Rubber Ducky Resort

Our cozy one room camping cabin will make camping easy. Our cabin has a picnic table, BBQ, fire pit and 6 foot covered deck perfect for relaxing and gazing at the stars. Cabin 43 is equipped with a double bed, bunk beds, table, and bar fridge. Campers just need to bring their own linens, utensils, and anything else needed to create a comfortable stay. Clean, modern washrooms and showers are just a short walk from your cabin. The Rec Building is open year round

Guest favourite

Tiny home in Richer

4.76 out of 5 average rating, 34 reviews

Rosie's Place

You’ll treasure your time at this memorable place. This tiny home has some unique and creative decor. Enjoy stepping back in time but with the modern amenities. This little house is great for a family getaway, but still great for group of freinds or just for a couples getaway. Has one master bedroom with a queen bed. And a loft with 2 single beds. Kitchette, BBQ on covered deck. Beach side firepit.

Guest favourite

Tiny home in Richer

4.84 out of 5 average rating, 131 reviews

Little beach cabin

Need a place to relax with your significant other, or maybe just get away on your own? Located in Wild Oaks Campground this cute little Beach Cabin makes for the perfect summer getaway. Take a dip in the pond, or relax on the beach. Whether you decide to enjoy the hot tub and pool, or get cozy by the fire this Cabin is sure to make for a memorable stay!

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Popular amenities for Winnipeg rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in West Saint Paul

4.71 out of 5 average rating, 45 reviews

Beautiful dreaming house 5 Bdrooms

JadeRating, 5 stars6 days ago

Lots of space if travelling with a group or family. The property was very nice and spacious. Host was responsive. We had a great time staying here. We didn’t get a chance to swim but the pool and trampoline were a great bonus to this property!!

Home in Winnipeg

3.67 out of 5 average rating, 3 reviews

Exclusive Luxury 4Br Villa w/ Pool & Table Tennis

TamaraRating, 5 stars4 weeks ago

I had a fantastic experience at this Airbnb! The location was ideal, with everything I needed just a short walk away. The place was clean and well-maintained, and the cozy bed was super comfortable. I would definitely recommend this spot for anyone looking for a convenient and relaxing stay!

Top guest favourite

Home in Winnipeg

4.98 out of 5 average rating, 61 reviews

Pool season ! Kg bed, Pet friendly & attached Grg

ElijahRating, 5 stars1 week ago

My partner and I thoroughly enjoyed our stay at Sandy's house! Our check in was easy and we instantly felt so relaxed. Everything was set up beautifully and was easy to find. Sandy was a phenomenal host and was very friendly and communicative throughout our stay. The house and property were immaculate and felt so well taken care of. We were drawn in to rent by the pool and hot tub, but the rest of the house made everything feel that much more special. Our dog loved the space in the back yard and we really enjoyed spending our days by the pool together. I would definitely recommend anyone to stay at Sandy's house!