Vacation Rentals with Pool in Ontario

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Filtering by: Swimming pool

441 vacation rentals

(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

    $556

    Price per night from

    $556

    (3) Excellent 

      30

      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

      $129

      Responds fast!
      avg. 1 hour 1 minutes

      Price per night from

      $129

        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

        $364

        Price per night from

        $364

          22

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

          Ontario / Toronto

          Toronto condo

          1 3 5 nights min

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

          Price per night from

          $145

          Price per night from

          $145

          (31) Excellent 

            104

            8 Acre Wood Cottage Dorset, Algonquin & Huntsville

            Lake of Bays / Dorset

            Dorset cottage

            5 24 min stay varies

            • 5 bedrooms
            • sleeps 24
            • min stay varies
            • Nearest beach 10 mi
            • Swimming pool
            • Child Friendly

            Price per night from

            $256

            Responds fast!
            avg. 3 hours 0 minutes

            Price per night from

            $256

            (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

              $415

              Price per night from

              $415

                46

                Breathtaking Waterfront @ Sandbanks

                Prince Edward County / Cherry Valley

                Cherry Valley cottage

                3 6 min stay varies

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

                Price per night from

                $214

                Price per night from

                $214

                (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

                  $343

                  Price per night from

                  $343

                  (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

                    $116

                    Responds fast!
                    avg. 25 minutes

                    Price per night from

                    $116

                    (1) Excellent 

                      28

                      The Grand View at Blue Mountain

                      Blue Mountains / Craigleith

                      Craigleith condo

                      2 6 1 night min

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

                      Price per night from

                      $129

                      Price per night from

                      $129

                        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

                        $67

                        Price per night from

                        $67

                        (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

                          $179

                          Responds fast!
                          avg. 37 minutes

                          Price per night from

                          $179

                          (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

                            $428

                            Responds fast!
                            avg. 3 hours 15 minutes

                            Price per night from

                            $428

                            (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

                              $171

                              Responds fast!
                              avg. 2 hours 9 minutes

                              Price per night from

                              $171

                              (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

                                $214

                                Price per night from

                                $214

                                (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

                                  $171

                                  Responds fast!
                                  avg. 3 hours 55 minutes

                                  Price per night from

                                  $171

                                  (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

                                    $170

                                    Responds fast!
                                    avg. 2 hours 29 minutes

                                    Price per night from

                                    $170

                                    (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

                                      $167

                                      Responds fast!
                                      avg. 51 minutes

                                      Price per night from

                                      $167

                                      (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

                                        $129

                                        Responds fast!
                                        avg. 1 hour 20 minutes

                                        Price per night from

                                        $129

                                          8

                                          Collingwood Resort Sleeps 4-Elvis Presley Festival

                                          Ontario / Collingwood

                                          Collingwood hotel apartment

                                          1 4 7 nights min

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

                                          Price per night from

                                          $167

                                          Price per night from

                                          $167

                                          (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

                                            $321

                                            Price per night from

                                            $321

                                            (1) Excellent 

                                              10

                                              Welcome to Nirvana, downtown Toronto!

                                              Ontario / Toronto

                                              Toronto condo

                                              2 4 2 nights min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 2 nights min
                                              • Swimming pool
                                              • Child Friendly
                                              • Car not necessary

                                              Price per night from

                                              $265

                                              Price per night from

                                              $265

                                              (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

                                                $343

                                                Responds fast!
                                                avg. 3 hours 14 minutes

                                                Price per night from

                                                $343

                                                (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

                                                  $99

                                                  Responds fast!
                                                  avg. 1 hour 37 minutes

                                                  Price per night from

                                                  $99

                                                    29

                                                    Sandy Shore Cottages Resort

                                                    Ontario / Harwood

                                                    Harwood cottage

                                                    2 6 2 nights min

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

                                                    Price per night from

                                                    $223

                                                    Price per night from

                                                    $223

                                                    (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

                                                      $77

                                                      Responds fast!
                                                      avg. 44 minutes

                                                      Price per night from

                                                      $77

                                                      (2) Excellent 

                                                        12

                                                        Renewed Resort Style Getaway Barrie w/ Pool!

                                                        Ontario / Barrie

                                                        Barrie house

                                                        3 8 min stay varies

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

                                                        Price per night from

                                                        $128

                                                        Responds fast!
                                                        avg. 2 hours 28 minutes

                                                        Price per night from

                                                        $128

                                                          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

                                                          $145

                                                          Price per night from

                                                          $145

                                                            34

                                                            The Richmond House

                                                            Prince Edward County / Bloomfield

                                                            Bloomfield house

                                                            5 14 min stay varies

                                                            • 5 bedrooms
                                                            • sleeps 14
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $501

                                                            Price per night from

                                                            $501

                                                            (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

                                                              $154

                                                              Responds fast!
                                                              avg. 1 hour 23 minutes

                                                              Price per night from

                                                              $154

                                                              (3) Excellent 

                                                                14

                                                                Executive Rentals 2 BR + Den in Mississauga - 1907O1

                                                                Ontario / Mississauga

                                                                Mississauga apartment

                                                                3 6 min stay varies

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

                                                                Price per night from

                                                                $120

                                                                Responds fast!
                                                                avg. 1 hour 37 minutes

                                                                Price per night from

                                                                $120

                                                                (1) Excellent 

                                                                  31

                                                                  Bright, Sunny 1 Bedroom Private Apartment

                                                                  Clearview Township / Stayner

                                                                  Stayner apartment

                                                                  1 4 1 night min

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • 1 night min
                                                                  • Nearest beach 8 mi
                                                                  • Swimming pool
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $54

                                                                  Responds fast!
                                                                  avg. 16 minutes

                                                                  Price per night from

                                                                  $54

                                                                  (1)  

                                                                    16

                                                                    Stay up in the clouds on the 48th Floor

                                                                    Ontario / Toronto

                                                                    Toronto apartment

                                                                    1 5 1 night min

                                                                    • 1 bedroom
                                                                    • sleeps 5
                                                                    • 1 night min
                                                                    • Swimming pool
                                                                    • Car not necessary

                                                                    Price per night from

                                                                    $120

                                                                    Responds fast!
                                                                    avg. 1 hour 45 minutes

                                                                    Price per night from

                                                                    $120

                                                                      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

                                                                      $300

                                                                      Price per night from

                                                                      $300

                                                                      (3) Very Good 

                                                                        9

                                                                        Smooth - Luxury Exec Condo All In Financial Dist

                                                                        Ontario / Toronto

                                                                        Toronto apartment

                                                                        1 4 30 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 4
                                                                        • 30 nights min
                                                                        • Swimming pool
                                                                        • Air conditioning
                                                                        • Pet Friendly
                                                                        “Great selection, great service!” My wife and I made a rush decision to move to Toronto and had only 3 days to find a place. Taris and Lea were phenomenal! What a pleasure working with them. We told them what we were looking for and they delivered i

                                                                        Price per night from

                                                                        $112

                                                                        Price per night from

                                                                        $112

                                                                          16

                                                                          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

                                                                          $129

                                                                          Responds fast!
                                                                          avg. 59 minutes

                                                                          Price per night from

                                                                          $129

                                                                            14

                                                                            Beautiful Lake and City View Condo

                                                                            Ontario / Toronto

                                                                            Toronto condo

                                                                            1 5 2 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 5
                                                                            • 2 nights min
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $149

                                                                            Responds fast!
                                                                            avg. 3 hours 25 minutes

                                                                            Price per night from

                                                                            $149

                                                                            (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

                                                                              $99

                                                                              Price per night from

                                                                              $99