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Vacation rentals with a pool in Vaughan

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Vaughan

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

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Condo in Toronto

4.81 out of 5 average rating, 302 reviews

Spacious Downtown (midtown) 2bed 2 bath free parki

In the heart of Midtown (close to downtown), this is a modern 2 Bedroom, 2 Bathroom, 900 square foot loft, in a high rise building. My place is perfect for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends (pets) are welcome too! The condo is in pristine condition with a fully equipped kitchen, living area, two comfy beds, two full piece washrooms and a balcony with all the luxuries and amenities you need. My spot is close to Underground Subway Train Station - Yellow Line, 24/7 Bus Accessible, Yonge Street, 24 hour restaurants, 24 hour grocery store, Bars, Clubs, Restaurants, Movies, Highway 401. There is no shortage of things to do around here. Thank you for considering staying with me during your visit to Toronto. Whether you're coming for business, pleasure, or to visit family, I think you will tremendously enjoy my suite and my neighborhood.

Jul. 24 – 31

$346 CAD per night

Guest favourite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 215 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...

Apr. 24 – May 1

$184 CAD per night

Guest favourite

Guesthouse in Orangeville

4.95 out of 5 average rating, 310 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Sep. 16 – 23

$235 CAD per night

Guest favourite

Villa in Toronto

4.94 out of 5 average rating, 116 reviews

➊ The One Toronto Villa - Indoor Pool&Tennis Court

The One is a unique luxurious private midle-century modern villa escape in the center of north Toronto. Having a stunning and spacious lawn for events and social gathering, this modern house is featured a thermostatic indoor swimming pool. Being inspired from a farmhouse building, the house offering a traditional touch on the vintage furniture and a rustic interior that gives a warm and cozy feelings. It is a great escape from the hustle and bustle of city life without going out of town.

Sep. 26 – Oct. 3

$1,670 CAD per night

Guest favourite

Condo in Toronto

4.93 out of 5 average rating, 230 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.

Jan. 20 – 27

$363 CAD per night

Guest favourite

Farm stay in Essa

4.99 out of 5 average rating, 119 reviews

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!

Mar. 20 – 27

$246 CAD per night

Guest favourite

Guest suite in Orangeville

4.92 out of 5 average rating, 656 reviews

Private HotTub - Headwaters Retreat

Escape to our cozy and rustic queen suite with a modern touch. Private entrance & hot tub steps from your door, overlooking our peaceful conservation area. Spacious fireplace in main suite with en-suite bathroom, Apple TV, Netflix, and second bedroom with two twin beds. Steps from the hiking trails and just minutes from the town center. Perfect for outdoor adventures, art gallery visits, wine tours, weddings, sporting events, work trips or just a quiet getaway. Your getaway awaits!

Dec. 8 – 15

$121 CAD per night

Guest favourite

Cabin in Mono

4.94 out of 5 average rating, 273 reviews

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home and yoga studio, minutes to the Bruce Trail, Hockley Ski & Resort, and Mansfield Ski Club, enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Chef's creations and Private yoga and group classes available

Dec. 9 – 16

$260 CAD per night

Condo in Mississauga

4.78 out of 5 average rating, 189 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.

Dec. 16 – 23

$211 CAD per night

Guest favourite

Home in Toronto

4.91 out of 5 average rating, 264 reviews

King West Victorian Studio Gem

Victorian Century Home Quiet Residential Street in the Heart of Downtown Toronto Overlooks Park + Outdoor Public Pool Open Concept 735 sq ft Sunny, Exposed Brick, Chandeliers Hardwood Floors Throughout Soaring 11' Ceilings Fully Equipped Eat-in Kitchen Private Laundry Private Backyard/Garden Business Traveler Ready Steps to King Streetcar Minutes to Queen & King West Nightlife, Shops, Cafes + Restaurants & King West Theatre District Street Permit Parking

Dec. 9 – 16

$261 CAD per night

Guest favourite

Apartment in Newmarket

5.0 out of 5 average rating, 140 reviews

The Hilton BnB Adult Luxury Suite

A beautifully decorated open concept walkout suite in an elegant 2-story home with all the amenities, accommodates 1-2 adult guests, in Newmarket’s prestigious Stonehaven Estates. The Hilton BnB is located just 30 minutes from downtown Toronto. Dine by the warmth of a fireplace in the winter or relax and have a BBQ poolside in the summer. The suite is spacious and the grounds are breathtaking. Uniquely designed with luxury in mind!

Sep. 4 – 11

$193 CAD per night

Condo in Mississauga

4.82 out of 5 average rating, 221 reviews

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.

May 8 – 15

$217 CAD per night

Vacation rentals for every style

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Popular amenities for Vaughan rentals with a pool

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Air conditioning

House rentals with a pool

Guest favourite

Home in Gormley

4.95 out of 5 average rating, 38 reviews

Lovely Home, Big Backyard + Pool

Mar. 24 – 31

$248 CAD per night

Guest favourite

Home in Newmarket

5.0 out of 5 average rating, 7 reviews

Beautiful Pond View stay!

Dec. 22 – 29

$187 CAD per night

Guest favourite

Home in Newmarket

4.82 out of 5 average rating, 17 reviews

Cozy Pool house in Newmarket

May 26 – Jun. 2

$333 CAD per night

Guest favourite

Home in Alton

4.96 out of 5 average rating, 70 reviews

Cheerful 3 bedroom home with outdoor pool & hottub

Dec. 13 – 20

$345 CAD per night

Guest favourite

Home in Toronto

5.0 out of 5 average rating, 17 reviews

Central Location Near Transit & Shops w/ Parking!

Oct. 22 – 29

$1,069 CAD per night

Guest favourite

Home in Mississauga

4.95 out of 5 average rating, 22 reviews

Carrera Cove - Spacious 3BR - 5 Mins to Go Train

Nov. 1 – 8

$368 CAD per night

Guest favourite

Home in King City

4.83 out of 5 average rating, 12 reviews

Family Luxury Retreat

Dec. 12 – 19

$1,149 CAD per night

Guest favourite

Home in Uxbridge

5.0 out of 5 average rating, 15 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

Mar. 13 – 20

$374 CAD per night

Condo rentals with a pool

Guest favourite

Condo in Toronto

4.9 out of 5 average rating, 355 reviews

Beautiful condominium with gorgeous city view!

Oct. 9 – 16

$242 CAD per night

Guest favourite

Condo in Toronto

4.97 out of 5 average rating, 218 reviews

Chic, High-Rise Apartment with CN Tower Views

Jun. 1 – 8

$478 CAD per night

Condo in Toronto

4.86 out of 5 average rating, 178 reviews

Best View in Downtown 5 Star Luxury 1+1 w/office

May 14 – 19

$312 CAD per night

Guest favourite

Condo in Toronto

4.89 out of 5 average rating, 273 reviews

CENTRAL DOWNTOWN LUXURY APT STEPS TO CN TOWER/LAKE

Sep. 29 – Oct. 6

$715 CAD per night

Guest favourite

Condo in Toronto

4.94 out of 5 average rating, 230 reviews

Luxury 1 Bedroom Suite In Heart Of Toronto

Jul. 24 – 31

$545 CAD per night

Guest favourite

Condo in Toronto

4.95 out of 5 average rating, 170 reviews

Upscale Luxurious Condo Free Parking

Aug. 25 – Sep. 1

$324 CAD per night

Condo in Etobicoke

4.83 out of 5 average rating, 109 reviews

Modern High-Rise 2 Bedroom Apr. With 400sf Terrace

Jun. 30 – Jul. 7

$468 CAD per night

Guest favourite

Condo in Toronto

4.96 out of 5 average rating, 110 reviews

Modern Downtown Condo Free Parking/ Walk to Lake

May 12 – 19

$526 CAD per night

Quick stats about vacation rentals with a pool in Vaughan

Total rentals
100 properties
Wifi availability
100 properties include access to wifi
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1K reviews

Destinations to explore