Holiday rentals with a pool in Greater Toronto and Hamilton Area

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

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!

Loft in Niagara-on-the-Lake

4.89 out of 5 average rating, 409 reviews

Luxury In The Heart Of Wine Country

Hidden along the shores of the Niagara River, Grayden Estate is nestled on a quiet dead end street in beautiful Queenston/Niagara on the Lake. A short drive to Old Town and within a few minute walk or bike to world class wineries, art galleries, farmers markets, hiking trails, parks and the waterfront, Grayden Estate is the ideal location for a peaceful quiet getaway for anyone looking to surrender to the simple living quiet life. Complimentary tour bikes are available for use. Lic # 112-2023

Apartment in Niagara Falls

4.97 out of 5 average rating, 589 reviews

Free parking 10 min walk to Falls & attractions!

Beautifully decorated upper unit in a fully remodeled 1800's home just steps away from everything you will want to see! Casino Niagara is a 1 minute walk. As well, Clifton Hill and all the attractions that Niagara has to offer are located close to our home. Enjoy your morning coffee in our garden oasis and take a dip in our heated in-ground pool when you are ready to just sit back, relax and plan your next adventure! You will enjoy all the comforts of home while you explore our beautiful city!

4.99 out of 5 average rating, 179 reviews

Apartment 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.

4.9 out of 5 average rating, 218 reviews

Cottage in Innisfil

Utopia Villa and Spa

Welcome to Utopia where you will make amazing long lasting memories with your family and friends. Just minutes from the beach, grocery stores, gas stations, and anything else you can need. There is so much to do here that you will never want to leave! Imagine a day full of good food by the fireplace, a dip in the hot tub, relaxing in the sauna and playing in the game room. Treat yourself with a stay! House rule: No smoking/eating in hot tub. Breaking this rule will result in $500 fine.

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, 174 reviews

Farm stay in Essa

The Schoolhouse

Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!

4.95 out of 5 average rating, 105 reviews

Condo in Innisfil

Upscale Spa Getaway w/ Private Sauna

Welcome to our most Dramatic, Romantic Spa Getaway Suite! Reconnect with your loved one in our incredible professionally designed to play with all your senses PH suite, this escape will melt away all your woes and leave you feeling refreshed and relaxed! Cozy up to any of 3 fire elements and cleanse your soul in your own private in suite infrared Sauna! Cook up a gourmet meal in our fully equipped kitchen and brand new Weber BBQ! Catch some rays in our pool and hot tub, NOW OPEN!

4.99 out of 5 average rating, 148 reviews

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

4.88 out of 5 average rating, 114 reviews

Cabin in Fergus

Luxury Oasis!! Heated Pool☆Sauna ☆Hot tub☆4Patios

Featured in Forbes "5 Charming Towns In Ontario" A cottage which has more to offer than a resort. Be it Summer or Winter! Indulge in the longest waterfront view you've ever seen from a cottage, nestled atop a hill. With an array of luxurious amenities, including heated pool, sauna, hot tub, gym, outdoor kitchen, fire pit, and multiple patios, this retreat exceeds all expectations. 4 family rooms, offices, a chef's kitchen, 10-person dining area, your every need is catered to.

Home in Niagara-on-the-Lake

4.94 out of 5 average rating, 108 reviews

Winery Escape Oasis | Pool | Hot Tub | BBQ | Bar

Don't delay on booking your next winery escape trip to Niagara-on-the-Lake! Our luxury 3 bedroom home has an incredible fully fenced backyard oasis including a heated in-ground pool (open May- end of September), hot tub, gas BBQ and a charcoal grill, outdoor dining, sun loungers, and more! Whether you're travelling with family or friends for a fun trip, our home will be the perfect choice and include everything you'll need. We look forward to hosting you soon!

Holiday rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Bungalows

Intimate homes, inviting architecture

Apartments

Convenient locations with everyday essentials

Popular amenities for Greater Toronto and Hamilton Area rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 25 reviews

Home in Mississauga

Luxury House with a Bright Sunroom & a heated pool

MargieRating, 5 stars1 week ago

A perfect spot for a large group! The pool was great and the common space was large and comfortable! Bedrooms were good size and beds were comfy! Our host was gracious and even brought a birthday cake for my husband. Would definitely stay again!

Home in The Blue Mountains

4.89 out of 5 average rating, 227 reviews

Large 4 Br - 4.5 Bath; Sauna/Heated Pool/2 King

KayeeRating, 5 stars2 weeks ago

Great stay at Blue Mountain. The kiddos really enjoyed the game room and the pool table. it was also super convenient to be able to schedule free shuttle to pick up and drop off to and from the village. Even if couldn't catch the shuttle it's only 20 min walk.

4.93 out of 5 average rating, 220 reviews

Home in Port Perry

Home away from home with a hot tub and pool

CourtneyRating, 5 stars2 weeks ago

lovely spot for some quiet outside time. backyard is spacious and welcoming. plenty of options for seating to enjoy sun or shade. kitchen was absolutely amazing to prepare food in, well organized and nicely laid out. rooms were tidy and clean, plenty of space to sleep 6 comfortably. would highly recommend this spot

4.91 out of 5 average rating, 107 reviews

Home in Niagara Falls

Luxury Family Oasis W/ GameRoom/King Bed/Hot Tub

BrittanyRating, 5 stars1 week ago

This is the perfect place to stay at Niagara Falls! It’s located in a quiet neighborhood away from the busy tourist areas, but close enough to walk to all of the fun. It’s a 5 minute drive to the falls, and a 10-15 minute walk to Clifton Hill. We walked down to Clifton Hill every night for dinner/ shopping/ and entertainment, and even walked to the falls at night to see the lights. The house is beautiful, and is thoughtfully stocked with everything you could want or need. Our kids especially loved the attic playroom, full of toys, games, and books, the large basket of blocks in the living room, and the pool and hot tub out back. There are also several games and puzzles in the dining room. The two full bathrooms and one half bath were convenient, and the washer and dryer were definitely a perk as well. We would absolutely stay here again!

Home in Niagara-on-the-Lake

5 out of 5 average rating, 12 reviews

Pool Hot Tub Private Vineyard Oasis for 6 in NOTL

AdamRating, 5 stars4 weeks ago

Great location, surrounded by vineyards! Shawn was also very responsive and helpful. We ran into an issue where the hot tub broke the first day there. Shawn had a repairman out to fix it within 24 hours. I really appreciated that.

Home in Niagara-on-the-Lake

4.79 out of 5 average rating, 230 reviews

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool

ChandraRating, 5 stars3 weeks ago

Beautiful place. The hosts were so kind and helpful. The area is safe and so close to the outlets which was a huge plus for us ladies! Hope to stay there again one day!

4.85 out of 5 average rating, 75 reviews

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.

4.89 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.

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Condo rentals with a pool

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

Condo in Markham

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!

4.93 out of 5 average rating, 152 reviews

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.

4.89 out of 5 average rating, 143 reviews

Condo in Innisfil

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Tanuja KajalRating, 5 stars3 weeks ago

We had an amazing time at Kevin’s place! It was the perfect peaceful getaway from the city. The home was clean, comfortable, and exactly what we needed to relax and unwind. Kevin was a great host—very responsive to messages and incredibly accommodating, even allowing us a late check-out which we really appreciated. He provided clear and detailed instructions for accessing the place, which made everything smooth and easy. Thank you, Kevin, for being so thoughtful and welcoming. We’d definitely love to come back again!

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.

4.84 out of 5 average rating, 269 reviews

Condo in Mississauga

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

IrinaRating, 5 stars2 weeks ago

Our family of three were staying in Omar place. It is great place to stay and really convenient location. Good communication and quickly response. I am really recommended this place to stay.