Vacation Rentals with Pool in Ontario

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Filtering by: Swimming pool

421 vacation rentals

(4) Very Good 

24

Beaver Valley Chalet

Grey County / Kimberley

Kimberley chalet

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Nearest beach 16 mi
  • Swimming pool
  • Ski

Price per night from

$346

Price per night from

$346

(26) Excellent 

Certificate of Excellence

9

Luxurious 1 Bed Condo in Downtown with parking

Ontario / Toronto

Toronto condo

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Certificate of Excellence

Price per night from

$90

Responds fast!
avg. 1 hour 39 minutes

Price per night from

$90

(1) Excellent 

23

Luxury Estates

Ontario / Paris

Paris house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$491

Price per night from

$491

(31) Excellent 

104

8 Acre Wood Cottage Dorset, Algonquin & Huntsville

Lake of Bays / Dorset

Dorset cottage

5 24 2 nights min

  • 5 bedrooms
  • sleeps 24
  • 2 nights min
  • Nearest beach 10 mi
  • Swimming pool
  • Child Friendly

Price per night from

$259

Responds fast!
avg. 1 hour 57 minutes

Price per night from

$259

(4) Excellent 

27

Luxury 4Brd LAKE FRONT!! House with water access.

Ontario / Toronto

Toronto house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$419

Price per night from

$419

22

FREE Parking! Entertainment District, +40th Floor view, gym, pool and more

Ontario / Toronto

Toronto condo

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Swimming pool
  • Air conditioning

Price per night from

$112

Price per night from

$112

46

Breathtaking Waterfront @ Sandbanks

Prince Edward County / Cherry Valley

Cherry Valley cottage

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

Price per night from

$173

Price per night from

$173

(3) Excellent 

33

PRIME WATERFRONT LOCATION WITH AMAZING CN TOWER VIEW, NEXT TO UNION STATION

Ontario / Toronto

Toronto condo

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child Friendly

Price per night from

$113

Responds fast!
avg. 2 hours 9 minutes

Price per night from

$113

(2) Excellent 

12

Renewed Resort Style Getaway Barrie w/ Pool!

Ontario / Barrie

Barrie house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$129

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$129

(16) Excellent 

Certificate of Excellence

27

Bright, Cozy 1 bdrm apt. w/parking near Bluffs

Ontario / Toronto

Toronto apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Air conditioning

Certificate of Excellence

Price per night from

$70

Responds fast!
avg. 46 minutes

Price per night from

$70

(1) Excellent 

28

The Grand View at Blue Mountain

Blue Mountains / Craigleith

Craigleith condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$130

Price per night from

$130

(3) Very Good 

29

MUSKOKAN CLUB RESORT - YEAR-ROUND LUXURY

Muskoka Lakes / Port Carling

Port Carling villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$324

Price per night from

$324

(15) Very Good 

23

Cottage containing 2 executive suites

Ontario / Peterborough

Peterborough cottage

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

Price per night from

$216

Price per night from

$216

(12) Excellent 

24

New Luxury Furnished 2BR2BA Downtown Waterfront

Ontario / Toronto

Toronto condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$181

Responds fast!
avg. 37 minutes

Price per night from

$181

8

Off-Grid Solar Shipping Container Cottage

Kawartha Lakes / Bobcaygeon

Bobcaygeon cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$303

Price per night from

$303

18

Dragonfield House

Prince Edward County / Bloomfield

Bloomfield house

4 14 2 nights min

  • 4 bedrooms
  • sleeps 14
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$368

Price per night from

$368

(4) Excellent 

10

Executive Luxury Condo @ Bloor & Islington

Ontario / Toronto

Toronto apartment

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary
“Comfortable Condo in a Great Location” We were looking for a place to stay on our first visit to Toronto, knowing that we were also going to visit Niagra Falls, London and of course, Toronto, so location was important. Ideally, we wanted a place wit
…see more

Price per night from

$169

Price per night from

$169

(5) Excellent 

49

Pine Creek Acres Country Retreat

Ontario / Pelham

Pelham house

6 15 min stay varies

  • 6 bedrooms
  • sleeps 15
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$432

Responds fast!
avg. 3 hours 45 minutes

Price per night from

$432

(1) Excellent 

29

Luxury Studio Getaway at Blue Mountains!

Blue Mountains / Craigleith

Craigleith studio

Studio 4 2 nights min

  • Studio
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$130

Responds fast!
avg. 2 hours 4 minutes

Price per night from

$130

(10) Excellent 

12

Summerland Summerland

Prince Edward County / Picton

Picton house

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly

Price per night from

$130

Responds fast!
avg. 1 hour 24 minutes

Price per night from

$130

13

Crystal Serenity Cottage

Fort Erie / Crystal Beach

Crystal Beach house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$130

Responds fast!
avg. 1 hour 20 minutes

Price per night from

$130

(1) Excellent 

7

Beautiful Fully Furnished 2 Bedroom apartment

Ontario / Mississauga

Mississauga house

2 4 10 nights min

  • 2 bedrooms
  • sleeps 4
  • 10 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$150

Responds fast!
avg. 3 hours 55 minutes

Price per night from

$150

9

Forks in the Trail Bed and Breakfast

Ontario / Horseshoe Valley

Horseshoe Valley b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 13 mi
  • Swimming pool
  • Child Friendly

Price per night from

$169

Price per night from

$169

(4) Excellent 

78

A COZY COTTAGE+ HEATED POOL OASIS IN GREATER TORONTO : FREE WIFI,MOVIES, PARKING

Ontario / Richmond Hill

Richmond Hill bungalow

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$169

Responds fast!
avg. 1 hour 29 minutes

Price per night from

$169

8

Furnished One Bedroom Apartment - Full Kitchen - Ensuite Laundry - St. Lawrence

Ontario / Cardinal

Cardinal apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 5 mi
  • Swimming pool

Price per night from

$68

Price per night from

$68

(8) Excellent 

17

Utica Guest House Your Home Away from Home

Ontario / Port Perry

Port Perry b and b

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$117

Responds fast!
avg. 1 hour 5 minutes

Price per night from

$117

(2) Excellent 

38

Roseneath on Prideaux Cottage

Ontario / Niagara-on-the-Lake

Niagara-on-the-Lake house

2 6 35 nights min

  • 2 bedrooms
  • sleeps 6
  • 35 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$397

Price per night from

$397

(3) Excellent 

8

Westhaver Boutique Residences - Garden Terrace Suite

Ontario / Toronto

Toronto condo

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 7 mi
  • Swimming pool
  • Car not necessary

Price per night from

$171

Responds fast!
avg. 1 hour 47 minutes

Price per night from

$171

15

02 Bedroom Furnished Apartment - Bombay Suites

Ontario / Mississauga

Mississauga apartment

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$83

Price per night from

$83

(4) Excellent 

26

Lakeside Niagara

Ontario / Niagara Falls

Niagara Falls house

6 16 min stay varies

  • 6 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$51

Price per night from

$51

(2) Excellent 

22

Otter River Farms Guesthouse

Bayham / Port Burwell

Port Burwell guest house

5 16 2 nights min

  • 5 bedrooms
  • sleeps 16
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 11 mi
  • Swimming pool

Price per night from

$216

Price per night from

$216

18

Niagara Falls Family Vacation Home

Ontario / Niagara Falls

Niagara Falls house

4 11 min stay varies

  • 4 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$51

Price per night from

$51

20

3BD 2WR BEST VALUE FOR LARGE FAMILY, SQUARE ONE

Ontario / Mississauga

Mississauga condo

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly

Price per night from

$129

Responds fast!
avg. 2 hours 0 minutes

Price per night from

$129

(10) Very Good 

11

Waterfront 3 Bedroom Cottage by Sandbanks

Prince Edward County / Cherry Valley

Cherry Valley cottage

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child Friendly
“Beautiful cottage, great view, great spot.” Our family of 5 spent a week in this beautiful cottage. Cherry Beach Resort is a nice place : swimming pool, small beach, basketball court and more. 10-15min only from the beautiful Outlet Beach. The cottage
…see more

Price per night from

$130

Price per night from

$130

(1) Excellent 

11

3 Bedroom family Cottage in Muskoka (Lake of Bays)

Muskoka District / Lake of Bays

Lake of Bays cottage

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$302

Responds fast!
avg. 2 hours 52 minutes

Price per night from

$302

(2) Excellent 

19

PRIME WATERFRONT LOCATION WITH AMAZING LAKEVIEW

Ontario / Toronto

Toronto condo

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$87

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$87

(4) Very Good 

19

Bright and Clean 2 BR Suite - Rideau Canal (2d)

Ontario / Ottawa

Ottawa condo

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$87

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$87

(3) Very Good 

15

Self Catering Suite - near Stratford, Ont Canada

Ontario / Mitchell

Mitchell apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$100

Price per night from

$100