Holiday rentals with a pool in Pickering

4.98 out of 5 average rating, 49 reviews

Home in Scarborough

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

Surrounded By Nature,This East-End Toronto Gem Features A Heated 4Ft Deep Pool(Open May-Oct),Pergola w/Ample Seating+BBQ On An Over-Sized Deck.The HGTV Inspired Renos Will Make Your Stay Extra Special.A True Get-Away Where Lasting Memories Will Be Made! ✔ 5-7 Min to PanAM Centre, Toronto Zoo, Rouge Beach &Train Station ✔ 10 Min To Pickering Casino ✔ 35 Min to CNtower ✔ 35 Min To YYZ airport ✔ 5 Min Walk to TTC bus stop ✔ 5 Min To Groceries ✔ 5 Min To Highland Creek Village ✔ 10 Min To The Guild

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 384 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

4.95 out of 5 average rating, 105 reviews

Home in Scarborough

Modern Custom Home w/ Pool, Games & Parking

Welcome to our brand new, luxury modrn unit located in a quiet, family-friendly neighborhood only min from HWY401,407,DVP, TTC & countless amenities! Newly & lovingly modern space with luxury finishes throughout. Enjoy comfortable living quarters, brand new kitchen appliances, bright rooms, large windows, a dedicated workspace, in-unit washer/dryer, free WIFI, Netflix, Prime & free parking. This upscale oasis is truly the perfect space for business travelers, young professionals & couples alike!

4.99 out of 5 average rating, 179 reviews

Flat in Newmarket

The Hilton BnB Adult Luxury Suite

Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

5 out of 5 average rating, 13 reviews

Home in North York

Award Winning Luxury Home with Heated Pool + Sauna

Winner of the 2023 RESA Home Staging Industry Award, my house was professionally designed to ensure my guests have a 5-star atmosphere to enjoy their stay. It has 3 bedrooms with 4 beds total, as well as 3.5 bathrooms and a sauna. It is fully equipped with everything you'll need including comfortable Fairmont Royal beds, high-speed WiFi, several 4K TV's, spacious rooms and a large backyard in a ravine lot. It has been recently renovated and has a brand new deck to relax on by the pool.

Apartment in Davisville Village

4.93 out of 5 average rating, 269 reviews

SpectacularPenthouse VIEWS/ POOL /free Parking

Sparkling clean, lovely Penthouse Unit with panoramic city view. Lots of amenities, great neighbourhood. The building is 2 mins from subway-which leads you to Downtown Toronto- in ten minutes. Lots of amazing restaurants and pubs in the area for your enjoyment and entertainment. There is a gym, salt water pool and sauna on the 4th floor and 24 hour security; a secured parking garage with a spot for guests to park free; and there is additional paid public parking in the underground.

4.99 out of 5 average rating, 148 reviews

Home in The Beaches

Heated Pool-tub Open 365 Days

Welcome to the Toronto Beach. We are right next to the lake and have a HEATED private pool and spa that are both open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails, and lots of walking to be had. We decorate for the holidays, and the house has a real wood burning fireplace. **note quiet hours are 11:00 pm to 7:00AM

4.93 out of 5 average rating, 220 reviews

Home in Port Perry

Home away from home with a hot tub and pool

This spacious home is a short walk to downtown Port Perry. Enjoy your time around the pool or hot tub, relaxing by the outdoor fireplace, lounging at the bar or just spending your time under a large covered deck ( rain or sunshine, uv ray protection). Port Perry offers shopping, fun at the lake (fishing and boating), skiing, hiking, local brewery, many restaurant choices and easy access to the Blue Heron casino. Check local web site for the many events going on around town.

4.84 out of 5 average rating, 50 reviews

Home in Pickering

Toronto Vacation Pool/Park/Zoo/Casino

Welcome to our newly renovated 4-bedroom home. This spacious and stylish accommodation offers both a living room and a family room for your comfort and convenience. Dive into relaxation with access to our private heated pool. We take pride in upholding high cleanliness standers to ensure your stay is comfortable and enjoyable. Whether you’re here for a family getaway or a group retreat, our home provides the perfect blend of comfort and convenience.

4.88 out of 5 average rating, 107 reviews

Loft in Etobicoke

Beautifully Updated 2 Storey Condo w/ outdoor pool

Don't miss this perfectly located, 2 storey corner suite! Fully upgraded with a modern appeal. Steps away from Lake Ontario, 15 Minutes away from YYZ & DT Toronto (traffic varies) ! Enjoy peaceful amenities such as outdoor pool, sauna rooms & patio. Gym. Restaurants, grocery stores, Pharmacy, LCBO all within a 5 minute drive away & walking distance. **No parties permitted 1 Free parking with unit!

4.84 out of 5 average rating, 269 reviews

Apartment in Mississauga

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

This beautiful sunfilled condo is newly furnished and well cared for, equipped with everything you need to make you feel right at home! Free Wifi included with Netflix access and underground parking. Amenitites in the building include a swimming pool and gym. located very conveniently in the heart of Mississauga, steps to Square one, Hwy 403, Pearson Airport and only a short drive to Downtown Toronto.

4.96 out of 5 average rating, 209 reviews

Guest suite in Uxbridge

Mackenzie Cottage

Historic Log home in a country oasis. Nestled in the forest with a large pool just outside the back door, and quick access to some of the most beautiful and exciting trails in southern Ontario. Inside, surround yourself with the warmth of a log cabin circa 1815, as well as the soaring ceilings of the newer post and beam structure. Visit us on Insta @allbrightlane

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Popular amenities for Pickering rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.81 out of 5 average rating, 31 reviews

Home in Oshawa

Private Pool + BBQ + PS4: 5 Bedooms, 3 Bathrooms!

KajaRating, 5 stars1 week ago

Neil was an amazing host for my large group! Extremely responsive and helpful with any questions you might have and the Airbnb + pool are lovely! The home was clean and as pictured in the listing would highly recommend!!!

4.92 out of 5 average rating, 75 reviews

Home in Scarborough

Ravine Paradise ! heated pool and hot tub!

CelesteRating, 5 stars3 weeks ago

this was one of the best airbnbs we stayed at. the place was clean and even more beautiful than described. Preston communicated with me months before we rented, through tech difficulties, before during and after the stay. they were understanding, courteous, and helpful. would stay here again, even my sister who visited inquired for the future.

5 out of 5 average rating, 34 reviews

Home in Uxbridge

Redwood Haven East: Your Dream Getaway in Uxbridge

SarahRating, 5 stars2 weeks ago

This is a wonderful Airbnb in a really special place away from the hustle and bustle of everyday life. You are in a quiet location within easy access of trails where you can run or walk and if you like to ride, there are plenty of equestrian places providing this facility including part of the Airbnb itself. Youssef and his family were welcoming and on hand to provide advice as needed. That said, they were never intrusive. The accommodation is spacious and homely and you certainly do not feel like rushing out but rather enjoying the facilities. There is everything that you could need for a short or extended stay. Towels were plentiful as were shampoo and lots of extras in the bathrooms and kitchen. The heated pool is a real bonus for children or adults that like a daily swim and although shared with the family, I never felt restricted in its use and loved the fact that it was heated so was comfortable regardless of the external temperature. A wonderful stay and perfect host.

4.85 out of 5 average rating, 75 reviews

Home in North York

Toronto Pool Retreat

JasonRating, 5 stars4 weeks ago

Meysam’s place was a great fit for our large group. The location was convenient for getting around, and the house offered everything we needed for a comfortable stay. There was plenty of space to cook and hang out together, and the hot tub was a nice feature. Overall, a solid spot for a group getaway.

4.87 out of 5 average rating, 46 reviews

Home in Mimico-Queensway

private backyard SPA oasis in Toronto

WadeRating, 5 stars2 weeks ago

Awesome 👌 property with above average amenities and spa style options available; the hotubs alone were top notch, clean, hot and easy to use. The house itself was beautiful, well laid out and very clean. anither great property if anyone is looking to be in the mix of it all plus having the extras in your own back yard.

Home in Central Etobicoke

4.89 out of 5 average rating, 9 reviews

Luxury 2bedroom Unit in the city/heated salt pool.

TanyaRating, 5 stars9 months ago

We had a great time at Bessa’s. The house was beautifully decorated. The pool and back yard were amazing. We will definitely be back. I would highly recommend staying here.

4.94 out of 5 average rating, 53 reviews

Home in Appleton

The Lakeshore Cottage

MattRating, 5 stars3 days ago

Beautiful home and beautiful setting. Everything was clean and just as described. We definitely hope to stay again!

4.91 out of 5 average rating, 305 reviews

Home in Niagara

King West Victorian Studio Gem

TamerRating, 5 stars6 days ago

It was great to stay at Kathleen's. The place is very spacious and perfect for a one person or a couple. The location is very close to a lot of nice restaurants, coffee shops, bars, and a lot more. I like the neighborhood a lot. In the summer, you can also enjoy the park right across the street. The place was very clean, and Kathleen was a great communicator - on top of everything. It really felt like home. I stayed there for one month as I was in between places and honestly I wish I could have stayed more.

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Apartment rentals with a pool

Apartment in Davisville Village

4.85 out of 5 average rating, 106 reviews

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

NhatRating, 5 stars1 day ago

Great location, the place is clean and the host is very responsive.

4.91 out of 5 average rating, 114 reviews

Apartment in Unionville

Downtown Markham Unionville

AndreaRating, 5 stars3 months ago

We had a great stay at Thomas' place. He met us at check in, showed us the building, parking and any details we needed to know. He was very responsive, provided early check in, and coordinated parking spots for both our vehicles. The place was very clean and quiet. We would definitely stay again!

Apartment in Downtown Toronto

4.89 out of 5 average rating, 101 reviews

Beautiful Condo Across CN Tower and MTCC

Daniela Rating, 5 stars5 months ago

I really enjoyed staying at William’s airbnb. Host was always responsive, professional and nice. The instructions were clear and easy to follow. Really recommend it!

4.93 out of 5 average rating, 152 reviews

Apartment in Toronto

Hidden gem in Humber bay shores Toronto w/ parking

RebeccaRating, 5 stars2 months ago

Super convenient area for getting around the city. Very clean and super friendly host.

Apartment in Downtown Toronto

4.97 out of 5 average rating, 245 reviews

Chic, High-Rise Apartment with CN Tower Views

KevinRating, 5 stars2 weeks ago

We were in town to attend a couple Jays games and see DT Toronto. This location was great for both. Also easy access to Union station. Condo was just right for us.

4.98 out of 5 average rating, 121 reviews

Apartment in Fort York

Artsy and Comfy Home with a View

YomiRating, 5 stars1 week ago

Great Location if you're visiting the city close to everything downtown. Great view as well being on the 20th floor. Very clean apartment. The host used white sheets, pillowcases and towels which is always a plus in my opinion. Free parking was a HUGE plus for me (Parked my car and walked everywhere). I would definitely stay again and would recommend to anyone.