Vacation rentals with a pool in Oshawa

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Top-rated rentals with a pool in Oshawa

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Guest favorite

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 290 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...

Guest favorite

Farm stay in Kawartha Lakes

4.88 out of 5 average rating, 121 reviews

Sky Haven Retreat & Equine Experience

LETS GET TOGETHER! Luxury spaces to host the whole family, Zen with horses, magnificent views. Private suite, Fire Pit, Covered patio, Hiking Trail, outdoor kitchen and BBQ. Billiards, shuffleboard, trampoline, table tennis, basketball, badminton, bocce ball. Something for everyone! Book an archery tag or axe throwing game! Sky Haven Equestrian in Bethany. On-site horse experiences and riding. Kids Stay Free! When booking enter number of adults only. Wutai Shan Bhuddist Garden is 4 min. away.

Guest favorite

Guest suite in Kawartha Lakes

4.96 out of 5 average rating, 119 reviews

Hidden Acres - a Stay and Play Retreat!

Are you looking for some nature therapy? You'll be nestled in several acres of forest, where you can hear the birds and enjoy the private backyard. The hot tub and campfire* beckon in all seasons, and the inground pool is open from mid-June to Labour Day each year. Please acknowledge that you read and understand our house rules when booking. Let us know who is coming, and provide details about your dog (breed, age, temperament). *We are excited to share that we now offer a Level 2 EV outlet!*

Guest favorite

Treehouse in Port Perry

4.98 out of 5 average rating, 553 reviews

Treehouse on private, isolated forest (300 acres)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

Guest favorite

Rental unit in Newmarket

4.99 out of 5 average rating, 163 reviews

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.

Guest favorite

Condo in Davisville Village

4.93 out of 5 average rating, 250 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.

Guest favorite

Guest suite in Lorne Park

4.93 out of 5 average rating, 149 reviews

Full apt on Upper floor near HWY - S Mississauga

Get the privacy & convenience of a hotel and comfort of a home. In the heart of Lorne Park in S. Mississauga, the apartment is built on the upper floor of a house with a separate entrance from the rear. One minute to QEW, 17 minutes from the airport, & 20 minutes to downtown Toronto, this spacious apartment is self-sufficient with a new, full kitchen with appliances, bathroom, laundry & parking. Ideal for all types of stays. A lot of our guests are repeat guests. No smoking property.

Guest favorite

Home in Port Perry

4.93 out of 5 average rating, 213 reviews

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.

Guest favorite

Home in The Beaches

4.99 out of 5 average rating, 118 reviews

Vacation Getaway:Heated Pool-Hottub Open 365 Days

Welcome to the Toronto Beach and to this century old home, right on the beach with a private pool and spa that is 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 (bring your own equipment) and lots of walking to be had. We decorate for for holidays, and the house has a real wood burning fireplace.

Superhost

Condo in Mississauga

4.76 out of 5 average rating, 206 reviews

Benetton Suite - Square One - 1 BR+Den+1 Parking

The Benetton Suite - Square One - 1 BR + Den + 1 Parking located in the heart of Mississauga, 600m from Square One Mall and 300m from Living Arts Centre. This centrally air-conditioned apartment. includes complimentary high speed wi-fi and 1 private parking free on site. Furnished in top quality style, the apartment has 2 bedrooms, a flat screen TV (with Netflix!), a fully equipped kitchen, dishwasher, microwave, washing machine, dryer with 1 bathroom with a bath.

Guest favorite

Condo in Mississauga

4.85 out of 5 average rating, 193 reviews

🔥Charming 1 BR Condo🔥 Steps To Square One!👌

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.

Guest favorite

Guest suite in Uxbridge

4.96 out of 5 average rating, 185 reviews

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

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oshawa rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favorite

Home in Ajax

4.91 out of 5 average rating, 35 reviews

Beautiful Cottage in Ajax

Guest favorite

Home in Scarborough

4.97 out of 5 average rating, 34 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

Guest favorite

Home in Scarborough

4.91 out of 5 average rating, 57 reviews

Ravine Paradise ! heated pool and hot tub!

Superhost

Home in Oshawa

4.75 out of 5 average rating, 12 reviews

PS4 + BBQ: 5 Bedroom, 3 Bath - 2 Units in 1!

Guest favorite

Home in Uxbridge

4.86 out of 5 average rating, 86 reviews

The Ridge Roost - Uxbridge Township

Superhost

Home in Ajax

4.83 out of 5 average rating, 12 reviews

Entire Modern Home | Spacious | Near Lake & Park

Guest favorite

Home in Brooklin

5 out of 5 average rating, 8 reviews

King Bed/Hot Tub/ Game Room/5 Bedrooms/Bungalow

Guest favorite

Home in Scarborough

4.93 out of 5 average rating, 112 reviews

Entire house with Pool, ravine, and nature trail

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Condo rentals with a pool

Guest favorite

Condo in Downtown Toronto

4.93 out of 5 average rating, 206 reviews

College Park :2Bd+2bth + Free parking

Guest favorite

Condo in Fort York

4.95 out of 5 average rating, 125 reviews

One Of A Kind Downtown Sanctuary w/ CN Tower View

Guest favorite

Condo in Fort York

4.89 out of 5 average rating, 404 reviews

Lakeside Condo Studio In Downtown Toronto

Superhost

Condo in Downtown Toronto

4.87 out of 5 average rating, 105 reviews

Luxury 1BR Executive Suite with Stunning Views!

Guest favorite

Condo in Fort York

4.89 out of 5 average rating, 124 reviews

Lakeside Downtown Oasis accommodating 4 ppl

Guest favorite

Condo in Downtown Toronto

4.9 out of 5 average rating, 283 reviews

Closest condo to Rogers Centre/CN tower in Toronto

Guest favorite

Condo in Downtown Toronto

5 out of 5 average rating, 113 reviews

Luxury Downtown Condo For 6 (Near CN Tower)

Guest favorite

Condo in Downtown Toronto

4.94 out of 5 average rating, 155 reviews

Stylish 1BR/2 bed CN Tower view, Free Parking

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Quick stats about vacation rentals with a pool in Oshawa

Total rentals
10 properties
Total number of reviews
190 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Oshawa Centre, Tribute Communities Centre, and NEB's Fun World

Vacation rentals with a pool in Oshawa

Top-rated rentals with a pool in Oshawa

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Oshawa rentals with a pool

House rentals with a pool

Home in Ajax

Home in Scarborough

Home in Scarborough

Home in Oshawa

Home in Uxbridge

Home in Ajax

Home in Brooklin

Home in Scarborough

Condo rentals with a pool

Condo in Downtown Toronto

Condo in Fort York

Condo in Fort York

Condo in Downtown Toronto

Condo in Fort York

Condo in Downtown Toronto

Condo in Downtown Toronto

Condo in Downtown Toronto

Quick stats about vacation rentals with a pool in Oshawa

Total rentals

Total number of reviews

Family-friendly rentals

Wifi availability

Popular amenities

Local attractions

Destinations to explore